A stone staircase leading up to a blue arched entrance, surrounded by lush greenery and birch trees.

Hotels in Stockbridge

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A large, multi-story building with a swimming pool, surrounded by dense greenery and trees.

A brick pathway lined with autumn foliage and pumpkins, leading to a white building with a porch decorated with hanging flowers.

A swimming pool with lounge chairs and umbrellas, surrounded by greenery and a building in the background.

A bar with wooden floors and shelves filled with bottles.

1. The Red Lion Inn

Stockbridge

$161

$230 total

includes taxes & fees

Nov 4 - Nov 5

A living room with a fireplace, leather sofas, and a dog.

A stone fountain surrounded by trees in a park setting.

2. The Inn at Stockbridge

Stockbridge

$365

$428 total

includes taxes & fees

Nov 1 - Nov 2

A two-story house with a brick entrance and a white facade.

A neatly arranged bedroom with a bed, bedside table, and a dresser.

A cozy room with a wooden floor, a dining table with a lamp, a chair, a cabinet, and a window with curtains.

A well-maintained garden with a swimming pool, surrounded by lush greenery and a white building.

3. The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

Stockbridge

$382

$462 total

includes taxes & fees

Nov 4 - Nov 5

A building with a porch and multiple windows, surrounded by purple flowers.

A hotel room with a large bed, a bathroom with a bathtub, a vanity with a mirror, and a window with curtains.

A café with a display case, a frozen food section, and a marketplace sign.

A living room with a sofa, armchair, coffee table, and a patterned rug.

4. Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires

South Lee

$117

$150 total

includes taxes & fees

Oct 26 - Oct 27

A lakeside setting with Adirondack chairs and a covered seating area, surrounded by trees and hills in the background.

A lakeside dock with kayaks and a covered boat ramp.

A lakeside lodge with a dock, fishing rods, and outdoor seating.

A dining area with large windows, wooden furniture, and a view of a lake.

5. The Black Swan Lee - Lenox, an Ascend Collection Hotel

Lee

$112

$125 total

includes taxes & fees

Nov 15 - Nov 16

A large house with a balcony and a grassy yard.

A two-story building with a gabled roof and a chimney.

A sign for The Little Lion Inn with a lion emblem, indicating a themed establishment.

A hotel room with two beds, a nightstand with a lamp, and a framed picture on the wall.

6. The Little Lion

Great Barrington

$115

$128 total

includes taxes & fees

Oct 22 - Oct 23

A modern hotel lobby with seating areas, tables, and a reception desk.

A coffee station with two coffee machines and a variety of coffee pods and cups.

A breakfast area with a counter, coffee machine, and a display of pastries.

A kitchenette with a microwave, coffee maker, and coffee cups.

7. Holiday Inn Express Hotel & Suites Great Barrington by IHG

Great Barrington

$83

$93 total

includes taxes & fees

Nov 18 - Nov 19

A hotel room with a bed, a desk, a television, a microwave, and a sofa.

A modern living room with a fireplace, two blue armchairs, and decorative vases on the mantel.

A hotel room with a sofa, armchair, desk with lamp, television, mini-fridge, and patterned carpet.

8. Quality Inn Lee - Lenox South

Lee

$93

$103 total

includes taxes & fees

Nov 10 - Nov 11

A red building with a sign reading "Shaker Mill Inn."

A covered patio with a round glass table and metal chairs, a wooden deck, and a view of trees and hills.

A stone fireplace with a television above it, a kitchen area to the left, and a wooden floor.

A cozy room with a bed, a sofa, a small table, and a desk. There are two lamps on the bed and a window with curtains.

9. Shaker Mill Inn

West Stockbridge

$124

$136 total

includes taxes & fees

Nov 3 - Nov 4

A modern bathroom with a freestanding bathtub, a fireplace, and two framed posters on the wall.

A view from a balcony with a wooden railing, a grassy landscape, and a mountain in the distance.

A swimming pool with a surrounding deck, a stone wall, and a building in the background.

A hotel room with a four-poster bed, two armchairs, a small table with a book, and a decorative canopy.

10. The Yankee Inn

Lenox

$106

$118 total

includes taxes & fees

Nov 1 - Nov 2

A Fairfield by Marriott hotel with a covered entrance, multiple stories, and a well-maintained lawn.

A modern hotel lobby with a seating area, a sofa, and a large window with curtains.

An indoor swimming pool with a diving board, lounge chairs, and a 'No Diving' sign.

A hotel lobby with multiple seating areas, including tables and chairs, a large flat-screen TV mounted on the wall, and a patterned carpet.

11. Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Great Barrington

$144

$160 total

includes taxes & fees

Nov 2 - Nov 3

A hotel room with a large bed, a desk with a coffee maker, a chair, a TV, and a window with curtains.

A living room with a patterned carpet, two sofas, a dining table, and chairs.

A hotel room with a sofa, a wooden table, a lamp, a telephone, and a painting on the wall.

A motel with a two-story structure, multiple rooms with red doors, and a central staircase.

12. Travelodge by Wyndham Great Barrington Berkshires

Great Barrington

$79

$88 total

includes taxes & fees

Oct 22 - Oct 23

A hotel room with two beds, a bedside table with a lamp, and a window with a view of greenery.

A hotel room with a wooden dresser, a television, a microwave, and a mirror.

A row of motel rooms with red doors, a covered walkway, and a view of mountains in the background.

A motel with a parking lot and several cars parked.

13. Monument Mountain Motel

Great Barrington

$67

$74 total

includes taxes & fees

Nov 1 - Nov 2

A hotel room with a bed, a desk, and two wall-mounted lamps.

A motel with a flagpole, a blue awning, and a parking lot.

A small kitchenette with a coffee maker, toaster, and cabinets. There is a red and green patterned floor and a plant on the left.

A hotel room with a bed, two bedside tables, a desk, two chairs, and a large window with a view of greenery.

14. Econo Lodge Lee - Great Barrington

Lee

$65

$73 total

includes taxes & fees

Nov 13 - Nov 14

A modern outdoor patio with seating, a fire pit, and a building with large windows and stone pillars.

A modern restaurant with wooden flooring, bar area, and seating arrangements.

A large, multi-story hotel with a symmetrical facade, multiple balconies, and a well-lit entrance.

An indoor swimming pool with clear glass walls, a hot tub area, and a seating area with chairs and tables.

15. Courtyard by Marriott Lenox Berkshires

Lenox

$126

$140 total

includes taxes & fees

Nov 1 - Nov 2

A group of people performing yoga in an outdoor setting with grass and trees.

A reception desk with a framed floral painting, a deer head, and a sign about pets.

A motel with a row of rooms, a parking lot, and a hilly backdrop.

A hotel room with a flat-screen TV, a microwave, a refrigerator, a wooden dresser, a bedside lamp, and a framed picture on the wall.

16. Pleasant Valley Motel West Stockbridge

West Stockbridge

$77

$84 total

includes taxes & fees

Oct 22 - Oct 23

A bathroom with a bathtub, a showerhead, and a towel rack.

A gym with exercise equipment including treadmills, a stationary bike, and free weights.

A spacious hotel lobby with multiple seating areas, large windows, and a television.

A hotel room with a bed, a nightstand with a lamp and phone, a chair, and framed pictures on the wall.

17. Hampton Inn & Suites Berkshires-Lenox

Lenox

$110

$122 total

includes taxes & fees

Nov 1 - Nov 2

A spacious indoor area with a reception desk, multiple seating arrangements, and a view of the outdoors through large windows.

A hotel reception area with framed artwork, a coffee machine, and a sign indicating 'Quality by Choice Hotels'.

A Quality Inn sign, a brick building, and a parking lot with cars.

A hotel room with a wooden desk, a television, a mirror, and a bathroom visible through an open door.

18. Quality Inn Great Barrington

Downtown Great Barrington

$76

$85 total

includes taxes & fees

Nov 10 - Nov 11

A snow-covered outdoor area with a patio, seating, and a covered dining area.

A dining area with a glass table, red walls, and framed artwork.

A two-story house with a balcony, a brick chimney, and a porch with Adirondack chairs.

A modern living room with a fireplace, comfortable seating, and a large window with curtains.

19. The Cornell Inn, Lenox & The Berkshires

Lenox

$156

$179 total

includes taxes & fees

Oct 27 - Oct 28

An indoor swimming pool with clear water, tiled floors, and a blue wall.

A reception area with a modern design, including a reception desk, a Holiday Inn Express sign, and a refrigerator stocked with beverages.

A modern hotel with a large entrance, multiple floors, and a well-lit facade.

A snack bar with shelves of snacks and a refrigerated display.

20. Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Pittsfield

$95

$106 total

includes taxes & fees

Nov 19 - Nov 20

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Go beyond your typical stay in Stockbridge

Our prices for hotels in Stockbridge are cheapest in May

Top landmarks in Stockbridge

Norman Rockwell Museum

9.4/10 (347 reviews)

Norman Rockwell Museum is 0.8 mi (1.2 km) from central Stockbridge, why not stop by during your stay. If you want to experience more of the culture Stockbridge has to offer, head to Berkshire Botanical Garden, Naumkeag Museum, and National Shrine of the Divine Mercy.

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National Shrine of the Divine Mercy

9.0/10 (83 reviews)

If seeing the sights is on your list of things to do, head to National Shrine of the Divine Mercy— just one of the landmarks located 0.5 mi (0.8 km) from central Stockbridge.

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Naumkeag Museum

9.4/10 (10 reviews)

If museums are on your list of things to see, then you might want to head to Naumkeag Museum, located in the heart of Stockbridge.If you want to see more of the museums in Stockbridge, you can easily walk to Mission House.

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Berkshire Botanical Garden

9.4/10 (14 reviews)

Ready for an education in local botany? Berkshire Botanical Garden should make your list of places to visit, located 1.2 mi (2 km) from central Stockbridge. Want to stretch your legs some more? Head to Naumkeag Museum and The Mount, both nearby.

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Schantz Galleries

7.2/10 (5 reviews)

Art fans might want to browse the collections at Schantz Galleries in Stockbridge. If you want to see more of the art galleries in Stockbridge, Norman Rockwell Museum and Art et Industrie aren't far.

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Stockbridge Bowl

Check out the water views and take some great vacation pics at Stockbridge Bowl in Stockbridge.

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Frelinghuysen Morris House and Studio

8.2/10 (10 reviews)

Frelinghuysen Morris House and Studio is 4.4 mi (7 km) from central Stockbridge, why not stop by during your stay. If you want to experience more of the culture Stockbridge has to offer, head to Tanglewood Music Center, Shakespeare and Company, and Lenox Library.

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Berkshire Theatre Festival

8.8/10 (3 reviews)

Berkshire Theatre Festival is 0.9 mi (1.5 km) from central Stockbridge, why not stop by during your stay. If you enjoy the show and want to see another, Shakespeare and Company and Tanglewood Music Center are both not far.

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Learn more about Stockbridge

Wander through Norman Rockwell's America at his museum, where small-town life springs from canvas to memory. The red-brick Main Street looks suspiciously like his famous Christmas painting because, well, it is. Summer brings world-class music when Tanglewood hosts the Boston Symphony Orchestra in nearby Lenox. History buffs can explore the Mission House and Naumkeag's elegant gardens with their curious blue stairs. The Berkshire Botanical Garden offers seasonal splendor without the crowds of bigger attractions. For a perfect afternoon, grab a coffee on Main Street before heading to the Housatonic River, where locals fish in spots they'll reluctantly share if asked nicely.

See all hotels in Stockbridge

Check out reviews of Stockbridge hotels guests love

The Inn at Stockbridge

Stockbridge

10/10 Exceptional

Kevin

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

Stockbridge

10/10 Exceptional

Charles

The Red Lion Inn

Stockbridge

10/10 Exceptional

Michael

A large, two-story house with a well-maintained lawn and a fence.

A spacious living room with a fireplace, a dining area with a table and chairs, and large windows offering a view of the outdoors.

A bedroom with a large bed, a fireplace, a bathtub, and a window with a view of greenery.

A dining area with a table set for two, a view of a green landscape through large windows, and outdoor seating with a view.

Devonfield Inn B&B

Lee

10/10 Exceptional

Anonymous traveler

A wooden deck with a table and chairs, surrounded by a metal railing, overlooking a lush green landscape with trees.

A red door with a wreath, number 5, and flower baskets on either side.

A white bench with bright pink cushions, a small potted plant, and decorative wall art including a sun and a crescent moon.

A window view of a garden with rocks, bushes, and trees.

The Red Door B&B

Lee

10/10 Exceptional

Rudi

A lakeside cabin with a reflection in the water, surrounded by autumn-colored trees.

A wooden cabin with a staircase leading to a deck, surrounded by trees and a gravel path.

A wooden wall with a white pendant light fixture.

A wooden deck with a dog silhouette against a backdrop of autumn foliage.

Prospect Berkshires

Egremont

10/10 Exceptional

Emily

An aerial view of a large estate with multiple buildings, surrounded by dense greenery and trees.

A spacious living room with a high ceiling, wooden beams, a fireplace, and a bookshelf filled with books.

A wooden interior with a table, chair, and a view of a red barn through an open door.

A spacious kitchen with wooden beams, a dining area with a large table and chairs, and a view of the outdoors through large windows.

Inn at Silver Maple Farm

East Chatham

10/10 Exceptional

Michelle

A two-story building with a sign reading "Chambéry Inn".

A hotel room with a large bed, a TV mounted above a fireplace, a desk, and a seating area with chairs.

A large, historic building labeled "Chambéry Inn" with a vintage turquoise truck parked in front.

A cozy room with a fireplace, a sofa, a table with a bottle and glasses, and a patterned pillow.

Chambery Inn

Lee

10/10 Exceptional

Elaine

A cozy living room with a fireplace, a bookshelf, a coffee table with a book, and a plaid sofa.

A room with a wooden floor, two red armchairs, a small table, and a window with a view of trees.

Wilder House Berkshires

Sheffield

10/10 Exceptional

joseph

Shaker Mill Inn

West Stockbridge

10/10 Exceptional

This was the most comfortable B&B I have every heard of let alone stayed at. It does not have the awkwardness of eating breakfast in a community room of strangers. All the breakfast amenities are in you room, including the food that is stock daily by the inn keepers, so you get to enjoy in the comforts of your room (which is a cozy as home). The room was so spacious and well kept. Every detail is thought of by the innkeepers and if they forgot something they are accessible and gracious to...

Joe

A modern living room with grey sofas, a wooden coffee table, a stone fireplace, and a kitchen in the background.

A hotel room with two beds, a desk, a TV, and a window with curtains.

A grassy outdoor area with four blue Adirondack chairs arranged in a circle.

East Rock Inn

Great Barrington

10/10 Exceptional

Heather

A modern kitchen with a central island, bar seating, and a dining area with chairs and a table.

A hotel with a covered entrance, multiple floors, and a landscaped area with flowers and shrubs.

A reception area with a wooden reception desk, modern pendant lighting, and a vertical garden wall.

An outdoor seating area with Adirondack chairs and a fire feature.

Element by Marriott Lenox Berkshires

Lenox

10/10 Exceptional

Jacqueline

A calm lake at dusk with a wooden dock and two chairs facing the water.

A room with two beds, a round mirror, a red box, and a hanging light fixture.

A two-story house with a covered porch, a driveway, and a lawn with outdoor seating.

A lakeside dock with chairs and a table, surrounded by greenery and a clear sky.

Berkshire Lake Lodge

Lee

10/10 Exceptional

brian

A building entrance with a large planter with purple flowers and a small tree.

A restaurant with a large open dining area, wooden tables and chairs, and a brick wall with a colorful mural.

A lobby with a red sofa, two armchairs, a wooden table with a vase, brick walls, and an ornate ceiling.

A spacious room with a large window, a brick wall, a sofa set, and a patterned carpet.

Hotel On North

Pittsfield

10/10 Exceptional

The Hotel on North is a thoughtful and beautiful transformation of 2 old contiguous buildings, a store and factory, into a hip and fun hotel. The spaces are extremely large and open from the common spaces to the guest rooms, including the bathrooms. The aesthetic is colorful and friendly rather than the cookie cutter faux luxury I usually find in expensive hotels. The quirky design features such as vintage furniture and painted floors are a great juxtaposition to the perfect bed linens and...

Steve

A rustic interior with wooden tables and chairs, brick walls, and a large wooden beam structure.

A poolside area with lounge chairs and blue umbrellas, surrounded by a forested area.

A cozy room with a wooden bench, a table with a pitcher, and a sofa with patterned cushions. Large windows with yellow blinds offer a view of greenery outside.

A wooden fire pit surrounded by six Adirondack chairs in a forested area.

Little Cat Lodge

Copake Falls

10/10 Exceptional

Elisabeth

A large, two-story house with a wrap-around porch, a covered front porch, and a small front yard.

A cozy living room with a fireplace, a blue sofa, a red armchair, and a coffee table with books and a teapot.

A loft bedroom with a sloped ceiling, a ceiling fan, a floor lamp, a bed with a patterned bedspread, a chair, and a small table.

A dining table set with a vase of flowers, a book, and cutlery.

Brook Farm Inn

Lenox

10/10 Exceptional

roberta

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Great Barrington

10/10 Exceptional

We were greeted by extremely friendly staff. Check in and check out was seamless. Room was very nice and immaculate. We especially liked the bathroom design - didn't have to trip over the toilet to get in the shower as in most hotels! Free breakfast was the usual fare, but in a very pleasant and uncrowded room. Appreciated the free US News and NY Times Beautiful indoor pool - wish we'd brought our bathing suits!

Anonymous traveler

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Pittsfield

10/10 Exceptional

Bruce

Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires

South Lee

10/10 Exceptional

I love this place and have stayed here before. Even with the precautions for COVID-19, my kids and I still had a great time. The check-in was smooth and safe. The room was clean and sanitized. In fact, we had to "break the seal" on the door to enter and the seal was evidence of the cleaning that was done. Of course, the arcade and movie theatre were closed, but that was no surprise. The pools were open and reservations required to ensure everyone could be safe and still have fun. Lots of...

David

Frequently Asked Questions

What hotels do travelers like in Stockbridge?

Guests like The Red Lion Inn, The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood and Berkshire Mountain Lodge.

Can I book refundable hotels in Stockbridge?

If you want the flexibility to change your plans to Stockbridge, most accommodations offer refundable* rates you can book. You can find these accommodations by searching our site and using the "fully refundable" filter to narrow down the results.

Where can I stay in Stockbridge if I want a vacation home instead of a hotel?

If you want to find a good alternative to a hotel, review our selection of 35 vacation homes. You can also consider one of the 5 apartments or 9 cottages.

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

The warmest months in Stockbridge are usually July and August with an average temp of 66°F. January and February are the chilliest months when the average temp is 27°F. The rainiest months are October and July.

Why should I book my Stockbridge hotel with Hotels.com?

There are plenty of reasons to book your Stockbridge travel with us: our free cancellations on selected hotels* gives you the flexibility you're looking for, 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.

Hotels in Stockbridge

Free cancellation options if plans change

Earn rewards on every night you stay

Save more with Member Prices

Check prices for these dates

Where to stay in Stockbridge?

1. The Red Lion Inn

2. The Inn at Stockbridge

3. The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

4. Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires

5. The Black Swan Lee - Lenox, an Ascend Collection Hotel

6. The Little Lion

7. Holiday Inn Express Hotel & Suites Great Barrington by IHG

8. Quality Inn Lee - Lenox South

9. Shaker Mill Inn

10. The Yankee Inn

11. Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

12. Travelodge by Wyndham Great Barrington Berkshires

13. Monument Mountain Motel

14. Econo Lodge Lee - Great Barrington

15. Courtyard by Marriott Lenox Berkshires

16. Pleasant Valley Motel West Stockbridge

17. Hampton Inn & Suites Berkshires-Lenox

18. Quality Inn Great Barrington

19. The Cornell Inn, Lenox & The Berkshires

20. Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Go beyond your typical stay in Stockbridge

Price trends for hotels in Stockbridge

October

Top landmarks in Stockbridge

Norman Rockwell Museum

National Shrine of the Divine Mercy

Naumkeag Museum

Berkshire Botanical Garden

Schantz Galleries

Stockbridge Bowl

Frelinghuysen Morris House and Studio

Berkshire Theatre Festival

Learn more about Stockbridge

Check out reviews of Stockbridge hotels guests love

The Inn at Stockbridge

10/10 Exceptional

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

10/10 Exceptional

The Red Lion Inn

10/10 Exceptional

Devonfield Inn B&B

10/10 Exceptional

The Red Door B&B

10/10 Exceptional

Prospect Berkshires

10/10 Exceptional

Inn at Silver Maple Farm

10/10 Exceptional

Chambery Inn

10/10 Exceptional

Wilder House Berkshires

10/10 Exceptional

Shaker Mill Inn

10/10 Exceptional

East Rock Inn

10/10 Exceptional

Element by Marriott Lenox Berkshires

10/10 Exceptional

Berkshire Lake Lodge

10/10 Exceptional

Hotel On North

10/10 Exceptional

Little Cat Lodge

10/10 Exceptional

Brook Farm Inn

10/10 Exceptional

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

10/10 Exceptional

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

10/10 Exceptional

Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires

10/10 Exceptional

Frequently Asked Questions

What hotels do travelers like in Stockbridge?