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Hotels in Bennington

November 2026
December 2026

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Oct 30 - Nov 1
Next weekend
Nov 6 - Nov 8

Where to stay in Bennington?

An indoor swimming pool with clear water, metal railings, and lounge chairs.
A hotel reception area with a reception desk, a chandelier, framed pictures, and a coffee station.
A hotel room with two beds, a desk with a television, and a window with a mountain view.
A Hampton Inn hotel with a covered entrance and a clear sign indicating a 16-foot clearance.

1. Hampton Inn Bennington

Hampton Inn Bennington
Bennington
$155
$169 total
includes taxes & fees
Nov 1 - Nov 2
Hampton Inn Bennington
A hotel reception area with a modern design, featuring a reception desk, seating area, and artwork on the walls.
A hotel room with a large bed, a nightstand with a lamp, a small table with flowers, and a sliding glass door leading to an outdoor area with chairs.
A two-story hotel with a covered entrance, large windows, and a landscaped front yard with flower beds.
A modern kitchen area with built-in appliances, wooden tables, and red chairs.

2. New Englander Inn Bennington

New Englander Inn Bennington
Bennington
$92
$100 total
includes taxes & fees
Oct 28 - Oct 29
New Englander Inn Bennington
A hotel room with a large bed, a desk with a chair, a balcony with a view, and a TV mounted on the wall.
A hotel room with two beds, a desk, a chair, a TV, and a window with a view of greenery.
A hotel room with a red sofa, a round wooden table, a black armchair, a bed, and a large window with a view of greenery.
A tree with a fallen trunk in a grassy area with a blue building in the background.

3. Hotel Vervana, Trademark Collection by Wyndham

Hotel Vervana, Trademark Collection by Wyndham
Bennington
$99
$107 total
includes taxes & fees
Nov 2 - Nov 3
Hotel Vervana, Trademark Collection by Wyndham
A two-story building with a white exterior, a porch with a white railing, and a staircase leading to the upper floor.
A bathroom with a sink, two hair dryers, and a mirror.
A hotel room with two beds, a rocking chair, a door, and a window with curtains.
A BENNINGTON MOTOR INN sign with amenities like free continental breakfast and free wireless internet.

4. Bennington Motor Inn

Bennington Motor Inn
Bennington
$75
$82 total
includes taxes & fees
Nov 8 - Nov 9
Bennington Motor Inn
A bedroom with a double bed, two chairs, a small table with a hat, and floral curtains.
A dining room with a brick floor, large windows, and a chandelier.
A stone gate with a lantern, surrounded by trees and a grassy area.
A large, two-story house with a covered porch and multiple chimneys.

5. The Four Chimneys Inn

The Four Chimneys Inn
Bennington
$249
$271 total
includes taxes & fees
Nov 2 - Nov 3
The Four Chimneys Inn
A large tree with orange leaves in a grassy field.
A room with wooden paneling, a window with a white curtain, an air conditioning unit, and a wooden hanger rack.
A hotel room with a wooden floor, a bed with white bedding, a desk with a chair, a bedside table with a lamp, and a window with a view of greenery.
A sign for Starlight Inn in Bennington, featuring a star logo and the number 357.

6. Starlight Inn

Starlight Inn
Bennington
$99
$108 total
includes taxes & fees
Oct 28 - Oct 29
Starlight Inn
A spacious living area with a high ceiling, a wooden staircase, and a built-in kitchen visible through an open door.
A building with a covered outdoor area, wooden benches, and potted plants.
A spacious living room with a wooden staircase, a television, a sofa set, and a fireplace.
A living room with a sofa, a coffee table, a chess table, a TV, and a gaming console.

7. Brittany Motel

Brittany Motel
Manchester Center
$86
$95 total
includes taxes & fees
Oct 28 - Oct 29
Brittany Motel
A room with wooden paneling, a piano, a chair, and a door leading to another room.
A traditional living room with a wooden ceiling, green curtains, a fireplace, and a large armchair.
A covered porch with wicker furniture, a patterned rug, and an American flag.
A two-story house with a front porch, a flag, and a gravel driveway.

8. South Shire

South Shire
Bennington
$196
$224 total
includes taxes & fees
Oct 29 - Oct 30
South Shire
A spacious living room with a fireplace, a piano, and a dining area with round tables and chairs.
A motel with a swimming pool, lounge chairs, and a sign for Knotty Pine Motel.
A kitchen with wooden cabinets, a stainless steel sink, a microwave, a kettle, a toaster, and a refrigerator.
A compact kitchen with a microwave, utensils, and a sink. A sliding door leads to a bedroom with a bed and a radiator.

9. Knotty Pine

Knotty Pine
Bennington
$151
$164 total
includes taxes & fees
Oct 27 - Oct 28
Knotty Pine
A bedroom with a fireplace, two beds, a chair, and a nightstand.
A large, two-story house with a central entrance, surrounded by trees and a mountain backdrop.
A living room with a fireplace, a sofa, a coffee table, and a view through a sliding glass door.
A living room with a fireplace, a sofa, a coffee table, a cabinet, and two chairs.

10. The Manchester View

The Manchester View
Manchester Center
$113
$124 total
includes taxes & fees
Nov 3 - Nov 4
The Manchester View
A two-story building with a patio area featuring outdoor seating and a stone fire pit.
A treats display with snacks and sundries.
A spacious living area with a fireplace, comfortable seating, and a stone accent wall.
A hotel with a covered entrance, a flagpole with an American flag, and a brick building with multiple windows.

11. Hampton Inn and Suites Manchester

Hampton Inn and Suites Manchester
Manchester Center
$128
$141 total
includes taxes & fees
Nov 8 - Nov 9
Hampton Inn and Suites Manchester
A cozy room with a fireplace, green sofas, a pool table, and a lamp.
A bedroom with a wooden floor, a bed with a white bedspread, a nightstand with a lamp, a dresser, and a television on the dresser.
A wooden interior with a dining table set for four, a wooden cabinet with glass doors, and a kitchen area with a refrigerator and cabinets.
A hotel hallway with wooden walls, a reception desk, and a sign indicating 'Employees Only'.

12. Bromley View Inn

Bromley View Inn
Bondville
$96
$105 total
includes taxes & fees
Nov 22 - Nov 23
Bromley View Inn
A spacious living area with a sofa, armchairs, a television, a fireplace, and a dining area with a table and chairs.
A red house with a white picket fence, surrounded by lush greenery and trees.
A two-story house with a porch and a garden area covered in yellow leaves.
A gazebo, a red barn, and a white house in a garden with trees and flowers.

13. Arlington Inn

Arlington Inn
Arlington
$202
$220 total
includes taxes & fees
Nov 1 - Nov 2
Arlington Inn
A patio with four wooden chairs and a table set on a stone platform, overlooking a natural landscape with trees and distant hills.
A modern kitchen with a curved island, bar stools, wine bottles, and a television.
A spacious dining area with multiple tables and chairs, large windows, and a view of the outdoors.
An indoor swimming pool with clear water, surrounded by chairs and a bench.

14. The Palmer House Resort, an Ascend Collection Hotel

The Palmer House Resort, an Ascend Collection Hotel
Manchester Center
$107
$135 total
includes taxes & fees
Nov 22 - Nov 23
The Palmer House Resort, an Ascend Collection Hotel
A cozy living room with two sofas, a coffee table, and a lamp. There is a wooden ceiling with exposed beams and a ceiling fan.
A cozy living room with wooden furniture, a coffee table, and a fireplace.
A cozy living room with a fireplace, a wooden coffee table, a sofa, and a lamp. There is a dog bed and a welcome sign on the floor.
A welcoming entrance with a 'WELCOME' sign, a red door, and various seasonal flowers and decorations.

15. The Olympia Lodge

The Olympia Lodge
Manchester Center
$193
$220 total
includes taxes & fees
Oct 30 - Oct 31
The Olympia Lodge
A cozy indoor space with a chalkboard sign advertising free fire entertainment from 7pm to 9pm.
A garden with various flowers and a stream.
A cozy interior with a fireplace, wooden furniture, and a large window offering a view of the city at night.
A modern building with a glass facade, a brick exterior, and a metal roof.

16. Toll Road Inn

Toll Road Inn
Manchester Center
$129
$142 total
includes taxes & fees
Nov 3 - Nov 4
Toll Road Inn
A large two-story house with a front porch and a well-maintained lawn.
A cozy interior with a bar area, wooden furniture, and a Christmas tree.
An aerial view of a residential area with houses, a tennis court, and a swimming pool.
A rustic interior with wooden beams, a fireplace, and a chandelier.

17. The Landgrove

The Landgrove
Londonderry
$171
$187 total
includes taxes & fees
Nov 2 - Nov 3
The Landgrove
A hotel room with two beds, a window with blinds, a desk with a television, and a lamp.
A reception desk with a wooden finish, a small plant, and a seating area with tables and chairs.
A lobby with a stone fireplace, leather sofas, and a reception desk.
A stone wall surrounding a swimming pool with a metal handrail.

18. The Black Bear Lodge at Stratton Mountain Resort

The Black Bear Lodge at Stratton Mountain Resort
Stratton
$149
$180 total
includes taxes & fees
Oct 27 - Oct 28
The Black Bear Lodge at Stratton Mountain Resort
A spacious kitchen with wooden cabinets, a large island, and a dining area with floral tablecloths.
A hotel room with a bed, bedside lamps, a telephone, a window with curtains, and an air conditioning unit.
A picnic table in a grassy field with a white building with a red roof in the background.
A two-story white building with a red roof, a small porch, and a signboard in front.

19. Four Winds Country Motel

Four Winds Country Motel
Manchester Center
$116
$128 total
includes taxes & fees
Nov 1 - Nov 2
Four Winds Country Motel
A mountain with autumn foliage and a bridge in the foreground.
A circular seating arrangement with Adirondack chairs around a central fire pit, set on a gravel area with a grassy field and trees in the background.
A room with four light-colored armchairs arranged around a wooden coffee table, a stone wall with a shelf, and a framed map on the wall.
A cozy restaurant with wooden tables and chairs, a kitchen area, and a 'GATHER' sign on the wall.

20. Aerie Inn of Vermont

Aerie Inn of Vermont
East Dorset
$127
$138 total
includes taxes & fees
Oct 27 - Oct 28
Aerie Inn of Vermont
View all properties

Check out pet-friendly hotels in Bennington

An indoor swimming pool with clear water, metal railings, and lounge chairs.
A hotel reception area with a reception desk, a chandelier, framed pictures, and a coffee station.
A hotel room with two beds, a desk with a television, and a window with a mountain view.
A Hampton Inn hotel with a covered entrance and a clear sign indicating a 16-foot clearance.

Hampton Inn Bennington

Hampton Inn Bennington
Bennington
$155
$169 total
includes taxes & fees
Nov 1 - Nov 2
Hampton Inn Bennington
A hotel room with a large bed, a desk with a chair, a balcony with a view, and a TV mounted on the wall.
A hotel room with two beds, a desk, a chair, a TV, and a window with a view of greenery.
A hotel room with a red sofa, a round wooden table, a black armchair, a bed, and a large window with a view of greenery.
A tree with a fallen trunk in a grassy area with a blue building in the background.

Hotel Vervana, Trademark Collection by Wyndham

Hotel Vervana, Trademark Collection by Wyndham
Bennington
$99
$107 total
includes taxes & fees
Nov 2 - Nov 3
Hotel Vervana, Trademark Collection by Wyndham
A spacious living area with a high ceiling, a wooden staircase, and a built-in kitchen visible through an open door.
A building with a covered outdoor area, wooden benches, and potted plants.
A spacious living room with a wooden staircase, a television, a sofa set, and a fireplace.
A living room with a sofa, a coffee table, a chess table, a TV, and a gaming console.

Brittany Motel

Brittany Motel
Manchester Center
$86
$95 total
includes taxes & fees
Oct 28 - Oct 29
Brittany Motel
A room with wooden paneling, a piano, a chair, and a door leading to another room.
A traditional living room with a wooden ceiling, green curtains, a fireplace, and a large armchair.
A covered porch with wicker furniture, a patterned rug, and an American flag.
A two-story house with a front porch, a flag, and a gravel driveway.

South Shire

South Shire
Bennington
$196
$224 total
includes taxes & fees
Oct 29 - Oct 30
South Shire
A two-story building with a patio area featuring outdoor seating and a stone fire pit.
A treats display with snacks and sundries.
A spacious living area with a fireplace, comfortable seating, and a stone accent wall.
A hotel with a covered entrance, a flagpole with an American flag, and a brick building with multiple windows.

Hampton Inn and Suites Manchester

Hampton Inn and Suites Manchester
Manchester Center
$128
$141 total
includes taxes & fees
Nov 8 - Nov 9
Hampton Inn and Suites Manchester
A spacious living room with a fireplace, a piano, and a dining area with round tables and chairs.
A motel with a swimming pool, lounge chairs, and a sign for Knotty Pine Motel.
A kitchen with wooden cabinets, a stainless steel sink, a microwave, a kettle, a toaster, and a refrigerator.
A compact kitchen with a microwave, utensils, and a sink. A sliding door leads to a bedroom with a bed and a radiator.

Knotty Pine

Knotty Pine
Bennington
$151
$164 total
includes taxes & fees
Oct 27 - Oct 28
Knotty Pine
A large tree with orange leaves in a grassy field.
A room with wooden paneling, a window with a white curtain, an air conditioning unit, and a wooden hanger rack.
A hotel room with a wooden floor, a bed with white bedding, a desk with a chair, a bedside table with a lamp, and a window with a view of greenery.
A sign for Starlight Inn in Bennington, featuring a star logo and the number 357.

Starlight Inn

Starlight Inn
Bennington
$99
$108 total
includes taxes & fees
Oct 28 - Oct 29
Starlight Inn
A large two-story house with a front porch and a well-maintained lawn.
A cozy interior with a bar area, wooden furniture, and a Christmas tree.
An aerial view of a residential area with houses, a tennis court, and a swimming pool.
A rustic interior with wooden beams, a fireplace, and a chandelier.

The Landgrove

The Landgrove
Londonderry
$171
$187 total
includes taxes & fees
Nov 2 - Nov 3
The Landgrove
A cozy room with a fireplace, green sofas, a pool table, and a lamp.
A bedroom with a wooden floor, a bed with a white bedspread, a nightstand with a lamp, a dresser, and a television on the dresser.
A wooden interior with a dining table set for four, a wooden cabinet with glass doors, and a kitchen area with a refrigerator and cabinets.
A hotel hallway with wooden walls, a reception desk, and a sign indicating 'Employees Only'.

Bromley View Inn

Bromley View Inn
Bondville
$96
$105 total
includes taxes & fees
Nov 22 - Nov 23
Bromley View Inn
A mountain with autumn foliage and a bridge in the foreground.
A circular seating arrangement with Adirondack chairs around a central fire pit, set on a gravel area with a grassy field and trees in the background.
A room with four light-colored armchairs arranged around a wooden coffee table, a stone wall with a shelf, and a framed map on the wall.
A cozy restaurant with wooden tables and chairs, a kitchen area, and a 'GATHER' sign on the wall.

Aerie Inn of Vermont

Aerie Inn of Vermont
East Dorset
$127
$138 total
includes taxes & fees
Oct 27 - Oct 28
Aerie Inn of Vermont
View all properties

You may also like hotels with pools in Bennington

An indoor swimming pool with clear water, metal railings, and lounge chairs.
A hotel reception area with a reception desk, a chandelier, framed pictures, and a coffee station.
A hotel room with two beds, a desk with a television, and a window with a mountain view.
A Hampton Inn hotel with a covered entrance and a clear sign indicating a 16-foot clearance.

Hampton Inn Bennington

Hampton Inn Bennington
Bennington
$155
$169 total
includes taxes & fees
Nov 1 - Nov 2
Hampton Inn Bennington
A hotel room with a large bed, a desk with a chair, a balcony with a view, and a TV mounted on the wall.
A hotel room with two beds, a desk, a chair, a TV, and a window with a view of greenery.
A hotel room with a red sofa, a round wooden table, a black armchair, a bed, and a large window with a view of greenery.
A tree with a fallen trunk in a grassy area with a blue building in the background.

Hotel Vervana, Trademark Collection by Wyndham

Hotel Vervana, Trademark Collection by Wyndham
Bennington
$99
$107 total
includes taxes & fees
Nov 2 - Nov 3
Hotel Vervana, Trademark Collection by Wyndham
A bedroom with a fireplace, two beds, a chair, and a nightstand.
A large, two-story house with a central entrance, surrounded by trees and a mountain backdrop.
A living room with a fireplace, a sofa, a coffee table, and a view through a sliding glass door.
A living room with a fireplace, a sofa, a coffee table, a cabinet, and two chairs.

The Manchester View

The Manchester View
Manchester Center
$113
$124 total
includes taxes & fees
Nov 3 - Nov 4
The Manchester View
A two-story building with a patio area featuring outdoor seating and a stone fire pit.
A treats display with snacks and sundries.
A spacious living area with a fireplace, comfortable seating, and a stone accent wall.
A hotel with a covered entrance, a flagpole with an American flag, and a brick building with multiple windows.

Hampton Inn and Suites Manchester

Hampton Inn and Suites Manchester
Manchester Center
$128
$141 total
includes taxes & fees
Nov 8 - Nov 9
Hampton Inn and Suites Manchester
A spacious living room with a fireplace, a piano, and a dining area with round tables and chairs.
A motel with a swimming pool, lounge chairs, and a sign for Knotty Pine Motel.
A kitchen with wooden cabinets, a stainless steel sink, a microwave, a kettle, a toaster, and a refrigerator.
A compact kitchen with a microwave, utensils, and a sink. A sliding door leads to a bedroom with a bed and a radiator.

Knotty Pine

Knotty Pine
Bennington
$151
$164 total
includes taxes & fees
Oct 27 - Oct 28
Knotty Pine
A large two-story house with a front porch and a well-maintained lawn.
A cozy interior with a bar area, wooden furniture, and a Christmas tree.
An aerial view of a residential area with houses, a tennis court, and a swimming pool.
A rustic interior with wooden beams, a fireplace, and a chandelier.

The Landgrove

The Landgrove
Londonderry
$171
$187 total
includes taxes & fees
Nov 2 - Nov 3
The Landgrove
A cozy indoor space with a chalkboard sign advertising free fire entertainment from 7pm to 9pm.
A garden with various flowers and a stream.
A cozy interior with a fireplace, wooden furniture, and a large window offering a view of the city at night.
A modern building with a glass facade, a brick exterior, and a metal roof.

Toll Road Inn

Toll Road Inn
Manchester Center
$129
$142 total
includes taxes & fees
Nov 3 - Nov 4
Toll Road Inn
A cozy living room with two sofas, a coffee table, and a lamp. There is a wooden ceiling with exposed beams and a ceiling fan.
A cozy living room with wooden furniture, a coffee table, and a fireplace.
A cozy living room with a fireplace, a wooden coffee table, a sofa, and a lamp. There is a dog bed and a welcome sign on the floor.
A welcoming entrance with a 'WELCOME' sign, a red door, and various seasonal flowers and decorations.

The Olympia Lodge

The Olympia Lodge
Manchester Center
$193
$220 total
includes taxes & fees
Oct 30 - Oct 31
The Olympia Lodge
A large red barn and a white house with a porch, surrounded by trees and a well-maintained lawn.
A wooden-paneled room with a white sofa, a red pillow, a dark wooden cabinet, and a television mounted on the wall.
A bar area with wooden flooring, a leather sofa, and a bar counter with a variety of liquor bottles.
A swimming pool with lounge chairs, a red building with a tower, and lush greenery.

The Inn at Manchester

The Inn at Manchester
Manchester Village Historic District
$155
$196 total
includes taxes & fees
Nov 5 - Nov 6
The Inn at Manchester
A covered patio area with a wicker sofa, a round table with drinks, and a chair.
A room with a fireplace, a sofa, a dining table with chairs, and large windows offering a view of the outside.
A spacious hotel lobby with a high ceiling, chandeliers, seating areas, and large windows.
A large indoor swimming pool with wooden beams and a central decorative element.

The Equinox Golf Resort And Spa

The Equinox Golf Resort And Spa
Manchester Village Historic District
$120
$186 total
includes taxes & fees
Nov 4 - Nov 5
The Equinox Golf Resort And Spa
View all properties

You can also stay at hotels with a hot tub in Bennington

An indoor swimming pool with clear water, metal railings, and lounge chairs.
A hotel reception area with a reception desk, a chandelier, framed pictures, and a coffee station.
A hotel room with two beds, a desk with a television, and a window with a mountain view.
A Hampton Inn hotel with a covered entrance and a clear sign indicating a 16-foot clearance.

Hampton Inn Bennington

Hampton Inn Bennington
Bennington
$155
$169 total
includes taxes & fees
Nov 1 - Nov 2
Hampton Inn Bennington
A room with wooden paneling, a piano, a chair, and a door leading to another room.
A traditional living room with a wooden ceiling, green curtains, a fireplace, and a large armchair.
A covered porch with wicker furniture, a patterned rug, and an American flag.
A two-story house with a front porch, a flag, and a gravel driveway.

South Shire

South Shire
Bennington
$196
$224 total
includes taxes & fees
Oct 29 - Oct 30
South Shire
A two-story building with a patio area featuring outdoor seating and a stone fire pit.
A treats display with snacks and sundries.
A spacious living area with a fireplace, comfortable seating, and a stone accent wall.
A hotel with a covered entrance, a flagpole with an American flag, and a brick building with multiple windows.

Hampton Inn and Suites Manchester

Hampton Inn and Suites Manchester
Manchester Center
$128
$141 total
includes taxes & fees
Nov 8 - Nov 9
Hampton Inn and Suites Manchester
A cozy indoor space with a chalkboard sign advertising free fire entertainment from 7pm to 9pm.
A garden with various flowers and a stream.
A cozy interior with a fireplace, wooden furniture, and a large window offering a view of the city at night.
A modern building with a glass facade, a brick exterior, and a metal roof.

Toll Road Inn

Toll Road Inn
Manchester Center
$129
$142 total
includes taxes & fees
Nov 3 - Nov 4
Toll Road Inn
A spacious living area with a sofa, armchairs, a television, a fireplace, and a dining area with a table and chairs.
A red house with a white picket fence, surrounded by lush greenery and trees.
A two-story house with a porch and a garden area covered in yellow leaves.
A gazebo, a red barn, and a white house in a garden with trees and flowers.

Arlington Inn

Arlington Inn
Arlington
$202
$220 total
includes taxes & fees
Nov 1 - Nov 2
Arlington Inn
A hotel room with two beds, a window with blinds, a desk with a television, and a lamp.
A reception desk with a wooden finish, a small plant, and a seating area with tables and chairs.
A lobby with a stone fireplace, leather sofas, and a reception desk.
A stone wall surrounding a swimming pool with a metal handrail.

The Black Bear Lodge at Stratton Mountain Resort

The Black Bear Lodge at Stratton Mountain Resort
Stratton
$149
$180 total
includes taxes & fees
Oct 27 - Oct 28
The Black Bear Lodge at Stratton Mountain Resort
A patio with four wooden chairs and a table set on a stone platform, overlooking a natural landscape with trees and distant hills.
A modern kitchen with a curved island, bar stools, wine bottles, and a television.
A spacious dining area with multiple tables and chairs, large windows, and a view of the outdoors.
An indoor swimming pool with clear water, surrounded by chairs and a bench.

The Palmer House Resort, an Ascend Collection Hotel

The Palmer House Resort, an Ascend Collection Hotel
Manchester Center
$107
$135 total
includes taxes & fees
Nov 22 - Nov 23
The Palmer House Resort, an Ascend Collection Hotel
A covered patio area with a wicker sofa, a round table with drinks, and a chair.
A room with a fireplace, a sofa, a dining table with chairs, and large windows offering a view of the outside.
A spacious hotel lobby with a high ceiling, chandeliers, seating areas, and large windows.
A large indoor swimming pool with wooden beams and a central decorative element.

The Equinox Golf Resort And Spa

The Equinox Golf Resort And Spa
Manchester Village Historic District
$120
$186 total
includes taxes & fees
Nov 4 - Nov 5
The Equinox Golf Resort And Spa
A swimming pool with a view of a barn and mountains in the background.
A rustic room with wooden floors, a metal cart, shelves with plants, and a refrigerator.
A wooden deck with potted plants, a white chair, and a scenic view of hills and trees.
A two-story house with a porch and outdoor seating area.

Hill Farm Inn

Hill Farm Inn
Arlington
$259
$507 total
includes taxes & fees
Nov 15 - Nov 16
Hill Farm Inn
A swimming pool with a stone border, surrounded by a snow-covered landscape and a wooden fence.
A snow-covered town with a church featuring a clock tower, surrounded by buildings and a mountain in the background.
A snow-covered landscape with a wooden cabin and modern buildings.
A bar area with wooden ceiling beams, bar stools, and a long counter with bottles and glasses.

Long Trail House at Stratton Mountain Resort

Long Trail House at Stratton Mountain Resort
Stratton
$355
$441 total
includes taxes & fees
Oct 27 - Oct 28
Long Trail House at Stratton Mountain Resort
View all properties

Go beyond your typical stay in Bennington

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Pet friendly
Pet friendly
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Pool
Pool
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Hot tub
Hot tub
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Resort
Resort
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Spa
Spa
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Family friendly
Family friendly
Cottage image
Cottage
Cottage
apart-hotel image
Apart hotel
Apart hotel
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Apart­ment
Apart­ment
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Condo
Condo
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Villa
Villa
Our prices for hotels in Bennington are cheapest in March

Price trends for hotels in Bennington

Pricing is based on two traveler single night rates
View properties in October

October

High 14°C / low 5°C. Cloudy most days.
14°
5°
7°
-1°
1°
-6°
-2°
-10°
0°
-9°
4°
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12°
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19°
8°
23°
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27°
16°
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11°
Monthly weather averages (˚C)

Top landmarks in Bennington

Bennington Battle Monument

9.0/10 (202 reviews)
Bennington Battle Monument is 0.4 mi (0.6 km) from central Old Bennington, why not stop by during your stay.
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Southern Vermont College

8.2/10 (22 reviews)
If you'd like to get a taste of Bennington student life, check out Southern Vermont College, located 1.1 mi (1.8 km) from central Bennington.
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Prospect Mountain Cross-Country Ski Center

9.0/10 (28 reviews)
Skiers and snowboarders might want to test out the slopes at Prospect Mountain Cross-Country Ski Center, a skiing spot located 0.5 mi (0.9 km) from central Woodford. If you master the slopes, Prospect Mountain Nordic Ski Center is also located nearby.
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Woodford State Park

8.8/10 (11 reviews)
Woodford State Park is 2.1 mi (3.3 km) from central Woodford, why not stop by during your stay.
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Bennington Center for the Arts

8.6/10 (22 reviews)
Bennington Center for the Arts is 0.8 mi (1.2 km) from central Bennington, why not stop by during your stay. If you have fun at Bennington Center for the Arts, you'll love Bennington Arts Guild Gallery, located nearby.
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Prospect Mountain Nordic Ski Center

8.6/10 (8 reviews)
Skiers and snowboarders might want to test out the slopes at Prospect Mountain Nordic Ski Center, a top skiing spot in the heart of Woodford. If you master the slopes, Prospect Mountain Cross-Country Ski Center is also located nearby.
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Bennington Museum

9.0/10 (50 reviews)
If museums are on your list of things to see, then you might want to head to Bennington Museum, located in the heart of Old Bennington.If you want to see more of the museums in Old Bennington, Robert Frost Stone House Museum isn't far either.
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Robert Frost Stone House Museum

9.2/10 (15 reviews)
If museums are on your list of things to see in Bennington, then you might want to head to Robert Frost Stone House Museum. If you want to see more of the museums in Bennington, Bennington Museum isn't far either.
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Bennington and related destinations

Beneath the watchful Bennington Battle Monument, this Vermont town blends Revolutionary War history with artistic flair. The Old First Church cemetery holds poet Robert Frost's grave, marked with his own "I had a lover's quarrel with the world." At Bennington Museum, Grandma Moses paintings capture rural life with childlike wonder and surprising depth. Downtown's historic buildings house pottery studios and galleries where local craftspeople continue centuries-old traditions. Hiking trails on Monument Mountain reward with panoramic views that inspired generations of painters. In winter, Prospect Mountain offers cross-country skiing through silent forests. Don't miss the quirky collection of covered bridges scattered throughout the surrounding countryside.

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A mountainous landscape with autumn foliage, a prominent church spire, and a winding road.

Check out reviews of Bennington hotels guests love

A two-story house with a porch, a fountain, and a flag.
A room with a large window, a round glass table with a lace tablecloth, and a potted plant on the table.
A large, two-story house with a wrap-around porch, a turret, and a flag.
A grand staircase with ornate woodwork, a floral-patterned carpet, and a potted plant.

Bentley House Bed and Breakfast

Bentley House Bed and Breakfast
Poultney

10/10 Exceptional

United States
Suzanne
Bentley House Bed and Breakfast
An outdoor deck with a wooden table and wicker chairs, surrounded by a wooden railing and string lights.
A bar area with wooden stools, a bar counter, and a liquor cabinet.
A wooden sign with an arrow pointing to the right, labeled "CHICKENS".
A cozy living room with a fireplace, wooden walls, a sofa, and a dining area.

The Wilmington Inn

The Wilmington Inn
Wilmington

10/10 Exceptional

United States
Sophia
The Wilmington Inn
A large red barn and a white house with a porch, surrounded by trees and a well-maintained lawn.
A wooden-paneled room with a white sofa, a red pillow, a dark wooden cabinet, and a television mounted on the wall.
A bar area with wooden flooring, a leather sofa, and a bar counter with a variety of liquor bottles.
A swimming pool with lounge chairs, a red building with a tower, and lush greenery.

The Inn at Manchester

The Inn at Manchester
Manchester Village Historic District

10/10 Exceptional

United States
Mary
The Inn at Manchester
A modern living room with a fireplace, large windows, and a cozy seating area.
A modern hotel room with a large bed, a desk, and a chair. There is a window with curtains, a painting of mountains, and a TV on the wall.
A large building with a symmetrical facade, a central entrance with a glass door, and two smaller structures on either side.
A modern living room with a large sofa, a coffee table, and a fireplace.

Inn At Mount Snow

Inn At Mount Snow
West Dover

10/10 Exceptional

United States
Steven
Inn At Mount Snow
A white two-story house with a front porch, a covered patio, and a well-maintained garden.
A dining table with plates of food, two glasses of white wine, and a bottle of wine.
A living room with a sofa, a coffee table, and a painting on the wall.
A bathroom with a glass shelf holding toiletries, a vase with sunflowers, and a window with blinds.

The Weston

The Weston
Weston

10/10 Exceptional

United States
Zje
The Weston
A restaurant with tables set for dining, chairs, and a fireplace in the background.
A bedroom with a large bed, bedside tables, a small bench, and a sofa in the corner.
A two-story building with a porch, American flag, and two white rocking chairs.
A room with a brown leather sofa, a wooden chest labeled "The Honorable Lieutenant Captain Greenwood's Bay," and two windows with floral curtains.

The Reluctant Panther Inn and Restaurant

The Reluctant Panther Inn and Restaurant
Manchester Village Historic District

10/10 Exceptional

United States
Anonymous traveler
The Reluctant Panther Inn and Restaurant
A two-story house with a snow-covered roof and yard, featuring multiple lit windows and a visible chimney.
A large, white two-story house with a stone wall and yellow flowers in the foreground.
A covered porch with wicker furniture, a white railing, and a view of greenery.
A traditional bedroom with a four-poster bed, a large bookcase, and a classic wooden floor.

The Inn at Ormsby Hill

The Inn at Ormsby Hill
Manchester Center

10/10 Exceptional

United States
Anonymous traveler
The Inn at Ormsby Hill
A large white building with a stone wall and a lawn covered in fallen leaves.
A room with two single beds, a desk, and a radiator.
A pathway leading to a gazebo in a park with a pond and trees.
A long banquet table set up in a rustic barn with string lights and paper lanterns.

Colonel Williams Inn

Colonel Williams Inn
Brattleboro

10/10 Exceptional

United States
Ann
Colonel Williams Inn
A bedroom with a bed, a desk, a chair, a window with blinds, and a nightstand with a lamp.
A staircase with wooden railings and a chandelier.
A cozy room with a fireplace, wooden beams, a bookshelf, and a television.
A swimming pool with a white fence, lounge chairs, and umbrellas, surrounded by lush greenery and a lake.

Farm Road Estate

Farm Road Estate
West Dover

10/10 Exceptional

United States
Susan
Farm Road Estate
A white colonial-style building with a symmetrical facade, central entrance, and a small porch with chairs.
A spacious living area with a staircase, a red door, and a large window.
A long wooden table with red placemats and multiple wine glasses arranged for a tasting.
A serene pond with a statue in the center, surrounded by lush greenery and trees.

Four Columns Inn

Four Columns Inn
Newfane

10/10 Exceptional

United States
Janene
Four Columns Inn
A rustic dining area with wooden beams, tables, chairs, and a fireplace.
An outdoor event space with tables set for dining, surrounded by a covered area with a transparent roof.
A living room with a sofa, ottoman, armchair, and a television on a stand.
A bedroom with a large bed, a bedside table, a lamp, and a view of the outdoors through a sliding door.

The Inn at Weathersfield

The Inn at Weathersfield
Perkinsville

10/10 Exceptional

United States
Robert
The Inn at Weathersfield
A large, multi-story building with a prominent stone facade and a metal roof, surrounded by landscaped gardens and a pedestrian bridge.
A spacious interior with a wooden staircase, a seating area with patterned cushions, and large windows allowing natural light.
An outdoor seating area with stone fire pit, chairs, and a red building in the background.
A bar area with wooden beams, red chairs, and a long wooden table.

The Williams Inn

The Williams Inn
Williamstown

10/10 Exceptional

United States
Silvia
The Williams Inn
A swimming pool with a view of a barn and mountains in the background.
A rustic room with wooden floors, a metal cart, shelves with plants, and a refrigerator.
A wooden deck with potted plants, a white chair, and a scenic view of hills and trees.
A two-story house with a porch and outdoor seating area.

Hill Farm Inn

Hill Farm Inn
Arlington

10/10 Exceptional

United States
Michael
Hill Farm Inn
A large, two-story building with a symmetrical facade, multiple windows, and a central entrance with a covered porch.
A spacious living room with a large window, a sofa, a chair, and a dining area.
A gazebo in a lush garden with flowering plants and a large tree.
A room with a large sliding glass door leading to a garden. Inside, there is a table with chairs and a small table with a vase.

Harbour House Inn

Harbour House Inn
Cheshire

10/10 Exceptional

United States
Anonymous traveler
Harbour House Inn
A bedroom with a double bed, two chairs, a small table with a hat, and floral curtains.
A dining room with a brick floor, large windows, and a chandelier.
A stone gate with a lantern, surrounded by trees and a grassy area.
A large, two-story house with a covered porch and multiple chimneys.

The Four Chimneys Inn

The Four Chimneys Inn
Bennington

10/10 Exceptional

United States
Randall
The Four Chimneys Inn
A garden with a swing set, a blue chair, and a flower bed.
A house with a porch, snow-covered ground, and a Christmas tree with lights.
A breakfast buffet setup with cereal, milk, juice, and pastries.
A garden with a wooden pergola, potted plants, and a lawn with chairs.

Maple Terrace Motel

Maple Terrace Motel
Williamstown

10/10 Exceptional

United States
Eric
Maple Terrace Motel
A two-story building with a bar and restaurant on the ground floor, a vintage car parked in front, and a sign indicating "Main Mountain".
A bar area with a long counter, green upholstered bar stools, and a variety of bottles and glasses on shelves.
A wooden sign with the text "MAIN + MOUNTAIN" and a logo above it.
A modern hotel room with a bed, a seating area with a chair and a small table, a TV mounted on the wall, and a window with curtains.

Main and Mountain Bar & Motel

Main and Mountain Bar & Motel
Ludlow

10/10 Exceptional

United States
Anonymous traveler
Main and Mountain Bar & Motel

Frequently Asked Questions

What hotels do travelers like in Bennington?

Guests like Hotel Vervana, Trademark Collection by Wyndham, Knotty Pine and Bennington Motor Inn.

Can I book a refundable accommodation in Bennington?

If you're looking for the flexibility to change your plans to Bennington, most properties offer refundable* rates you can book. You can see these accommodations by searching our site and using the "fully refundable" filter to narrow down the results.

Where should I consider staying in Bennington if I'm looking for a reasonably priced accommodation?

An inexpensive option worth considering is Hotel Vervana, Trademark Collection by Wyndham. You may want to browse more choices on our site, including 5 motels.

Where can I stay in Bennington if I want a vacation rental instead of a hotel?

If you're looking for a good alternative to a hotel, review our selection of 16 vacation homes. You can also consider one of the 8 apartments or 8 cottages.

What will the weather in Bennington be like during my vacation?

July and August are typically the warmest months in Bennington when the average temp is 66°F. January and February are the coldest months when the average temperature is 26°F. October and June are the months with the most rain.

Why should I book my Bennington accommodation with Hotels.com?

There are lots of reasons to book your Bennington trip with us: our free cancellations on selected hotels* gives you flexibility, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™** on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.