Hotels in Hillsdale

Free cancellation options if plans change

Earn rewards on every night you stay

Save more with Member Prices

Check prices for these dates

Tonight
Sep 24 - Sep 25
Tomorrow
Sep 25 - Sep 26
This weekend
Sep 25 - Sep 27
Next weekend
Oct 2 - Oct 4

Where to stay in Hillsdale?

A modern bedroom with a large bed, two bedside tables, and a textured wall behind the bed.
A living room with a sofa, a coffee table, a fireplace, and a ceiling fan.
A dining area with a wooden table, chairs, and a colorful striped rug.
A compact kitchen with a wooden countertop, a coffee machine, and a small shelf with a hair dryer and cups.

1. The Brooks Motel

The Brooks Motel
Hillsdale
$146
$163 total
includes taxes & fees
Sep 27 - Sep 28
The Brooks Motel
A rustic interior with wooden tables and chairs, brick walls, and a large wooden beam structure.
A house with a stone patio and wooden stools.
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.

2. Little Cat Lodge

Little Cat Lodge
Copake Falls
$199
$223 total
includes taxes & fees
Sep 27 - Sep 28
Little Cat Lodge
A spacious indoor area with a reception desk, multiple seating arrangements, and a view of the outdoors through large windows.
A Quality Inn sign, a brick building, and a parking lot with cars.
A hotel room with a bathroom, a bed, a desk, and a nightstand.
A hotel reception area with framed artwork, a coffee machine, and a sign indicating 'Quality by Choice Hotels'.

3. Quality Inn Great Barrington

Quality Inn Great Barrington
Great Barrington
$101
$113 total
includes taxes & fees
Oct 18 - Oct 19
Quality Inn Great Barrington
A hotel room with two beds, a bedside table with a lamp, and a window with a view of greenery.
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.
A hotel room with a wooden dresser, a television, a microwave, and a mirror.

4. Monument Mountain Motel

Monument Mountain Motel
Great Barrington
$76
$85 total
includes taxes & fees
Oct 25 - Oct 26
Monument Mountain Motel
A modern hotel lobby with seating areas, tables, and a reception desk.
A kitchenette with a microwave, coffee maker, and coffee cups.
A hotel room with two beds, a desk, a TV, and a window with curtains.
A coffee station with two coffee machines and a variety of coffee pods and cups.

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

Holiday Inn Express Hotel & Suites Great Barrington by IHG
Great Barrington
$129
$144 total
includes taxes & fees
Oct 25 - Oct 26
Holiday Inn Express Hotel & Suites Great Barrington by IHG
A modern building with a dark exterior, outdoor seating area with wooden chairs, and string lights.
A dining table set with plates of food, wine glasses, and bottles, with a chandelier above and shelves above holding glasses and bottles.
A modern living room with a sofa, armchair, and coffee table. There is a bed with a headboard and pillows, a lamp, and a shelf with items.
A dog standing at a door entrance with a wooden floor and a mat with paw prints.

6. the Alander

the Alander
Copake
$145
$162 total
includes taxes & fees
Sep 28 - Sep 29
the Alander
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 circular pool with a tiled edge, surrounded by a concrete deck and a grassy area with chairs and a small shed.
A hotel room with a sofa, a wooden table, a lamp, a telephone, and a painting on the wall.

7. Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires
Great Barrington
$75
$84 total
includes taxes & fees
Sep 27 - Sep 28
Travelodge by Wyndham Great Barrington Berkshires
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.
A hotel lobby with multiple seating areas, including tables and chairs, a large flat-screen TV mounted on the wall, and a patterned carpet.
A corner market with a sign reading "the Corner Market" and shelves stocked with various snacks and groceries.

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

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Great Barrington
$169
$189 total
includes taxes & fees
Sep 28 - Sep 29
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
A large house with a balcony and a grassy yard.
A room with a white desk, two floral chairs, a small round table with a plant, a hanging lamp, and two framed artworks on the wall.
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.

9. The Little Lion

The Little Lion
Great Barrington
$115
$128 total
includes taxes & fees
Oct 18 - Oct 19
The Little Lion
A lakeside cabin with a reflection in the water, surrounded by autumn-colored trees.
A wooden wall with a white pendant light fixture.
A wooden cabin with a bed, a chair, and a table by a large window overlooking a lake.
A wooden deck with a dog silhouette against a backdrop of autumn foliage.

10. Prospect Berkshires

Prospect Berkshires
Egremont
$365
$441 total
includes taxes & fees
Sep 27 - Sep 28
Prospect Berkshires
A modern living room with grey sofas, a wooden coffee table, a stone fireplace, and a kitchen in the background.
A grassy outdoor area with four blue Adirondack chairs arranged in a circle.
A sign for East Rock Inn with a mountainous logo, surrounded by lush greenery and a gravel path leading to a building.
A hotel room with two beds, a desk, a TV, and a window with curtains.

11. East Rock Inn

East Rock Inn
Great Barrington
$145
$162 total
includes taxes & fees
Oct 25 - Oct 26
East Rock Inn

12. Berkshire Travel Lodge

Berkshire Travel Lodge
Austerlitz
$75
$84 total
includes taxes & fees
Sep 27 - Sep 28
Berkshire Travel Lodge
A reception area with a fireplace, seating, and a doormat with the logo "Quality".
A modern living room with a fireplace, two blue armchairs, and decorative vases on the mantel.
A hotel room with a bed, a desk, a television, a microwave, and a sofa.
A modern kitchen with a coffee machine, a refrigerator, and a dining area with chairs and tables.

13. Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
Lee
$110
$122 total
includes taxes & fees
Oct 19 - Oct 20
Quality Inn Lee - Lenox South
A bedroom with a large bed, a dresser, a chair, and a mirror.
A room with a wooden floor, two red armchairs, a small table, and a window with a view of trees.
A cozy living room with a fireplace, a bookshelf, a coffee table with a book, and a plaid sofa.

14. Wilder House Berkshires

Wilder House Berkshires
Sheffield
$195
$218 total
includes taxes & fees
Sep 27 - Sep 28
Wilder House Berkshires
A group of people performing yoga in an outdoor setting with grass and trees.
A hotel room with a bed, two chairs, a small table, and a lamp.
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.
A motel with a row of rooms, a parking lot, and a hilly backdrop.

15. Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge
West Stockbridge
$77
$84 total
includes taxes & fees
Sep 27 - Sep 28
Pleasant Valley Motel West Stockbridge
A dining table with pastries, a coffee pot, and a vase of sunflowers.
A small cabin with two Adirondack chairs in a grassy field, surrounded by trees and a mountain in the background.
A large, two-story white building with a symmetrical facade, columns, and a central entrance.
A pool table in a room with a patterned rug, a shelf with decorative items, and a window with a view of greenery.

16. Granville House

Granville House
Housatonic
$224
$250 total
includes taxes & fees
Sep 27 - Sep 28
Granville House
A round wooden table with two wine glasses and a green bottle, set against a window with a view of a blue railing and trees.
A kitchenette with a refrigerator, coffee maker, toaster, and bread display.
A hotel room with a bed, a desk, and two wall-mounted lamps.
A motel with multiple rooms, a well-maintained lawn, and a stone pathway.

17. Econo Lodge Lee - Great Barrington

Econo Lodge Lee - Great Barrington
Lee
$69
$77 total
includes taxes & fees
Sep 30 - Oct 1
Econo Lodge Lee - Great Barrington
A large, multi-story building with a swimming pool, surrounded by dense greenery and trees.
A backyard with a swimming pool, lounge chairs, and a hot tub.
A covered porch with wicker furniture and hanging flower baskets.
A bar with wooden floors and shelves filled with bottles.

18. The Red Lion Inn

The Red Lion Inn
Stockbridge
$161
$230 total
includes taxes & fees
Sep 30 - Oct 1
The Red Lion Inn
A modern bathroom with a freestanding bathtub, a fireplace, and two framed posters on the wall.
A cozy room with a wooden desk, a chair with a blanket, a fireplace with a fire, a mirror, and a poster on the wall.
A hotel room with a four-poster bed, two armchairs, a small table with a book, and a decorative canopy.
A view from a balcony with a wooden railing, a grassy landscape, and a mountain in the distance.

19. The Yankee Inn

The Yankee Inn
Lenox
$109
$122 total
includes taxes & fees
Oct 25 - Oct 26
The Yankee Inn
A lakeside setting with Adirondack chairs and a covered seating area, surrounded by trees and hills in the background.
A dining area with large windows, wooden furniture, and a view of a lake.
A lodge with a large building and a dock by a lake, surrounded by forest.
A lakeside lodge with a dock, fishing rods, and outdoor seating.

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

The Black Swan Lee - Lenox, an Ascend Collection Hotel
Lee
$128
$143 total
includes taxes & fees
Sep 30 - Oct 1
The Black Swan Lee - Lenox, an Ascend Collection Hotel
View all properties
Our prices for hotels in Hillsdale are cheapest in April
Price trends for hotels in Hillsdale
Pricing is based on two traveler single night rates
View properties in September
Typical weather for Hillsdale
September
High 23°C / low 12°C. Sunny most days.
View properties in September
23°
12°
16°
7°
9°
0°
3°
-4°
0°
-8°
1°
-7°
6°
-3°
13°
3°
20°
9°
25°
13°
28°
17°
27°
16°
Monthly weather averages (˚C)

Top landmarks in Hillsdale

Catamount Aerial Adventure Park

6.4/10 (5 reviews)
Catamount Aerial Adventure Park is 2.2 mi (3.5 km) from central Hillsdale, why not stop by during your stay.
See properties

Copake Lake

Copake Lake is 0.7 mi (1.2 km) from central Copake Lake, why not stop by during your stay.
See properties

Hillsdale Town Hall

Hillsdale Town Hall is worth a visit when in central Hillsdale.
See properties

Community Library

Community Library is worth a visit, located 0.9 mi (1.4 km) from central Hillsdale.
See properties

Mosquito Island

Mosquito Island is 1.2 mi (1.9 km) from central Copake Lake, why not stop by during your stay.
See properties

Roe Jan Brewing Co.

You could stop off for a few afternoon drinks at Roe Jan Brewing Co. when visiting Hillsdale.
See properties

Learn more about Hillsdale

Hillsdale is well-known for its attractions such as Catamount Aerial Adventure Park and Catamount Ski Area. The city has something for everyone including sights like Hillsdale Town Hall and Copake Lake within a small-town setting.

See all hotels in Hillsdale
A landscape with a row of trees in autumn colors, a wooden fence, and a hilly background.

Check out reviews of Hillsdale hotels guests love

The Yankee Inn

The Yankee Inn

10/10 Excellent
"Facility was very clean. Staff pleasant. Enjoyed breakfast."
James 1-night trip
Posted less than an hour ago
The Yankee Inn
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

10/10 Excellent
"A solo travelers dream."
Robert 4-night trip
Posted 18 hours ago
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
Berkshire Mountain Lodge

Berkshire Mountain Lodge

8/10 Good
"One of the most important aspects of a good hotel is the smell of it when I first walk in the door. This lodge smelled clean and was clean. The second important thing is the customer service. This place was just okay. Polite but not very friendly. The third important aspect is the plumbing and that was just okay too. Workable enough so we didn’t have to ask for another room but the little soaps were tiny and the toilet was in okay condition. A little hard to flush sometimes. They act like it’s someplace special but it really isn’t. It was a good stay but nothing special. Location was convenient to everything - restaurants and stores."
Karen 2-night trip
Posted 19 hours ago
Berkshire Mountain Lodge
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

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

10/10 Excellent
"Every one was very kind and helpful."
Jean 1-night trip
Posted 2 days ago
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Holiday Inn Club Vacations Oak 'n Spruce Resort

Holiday Inn Club Vacations Oak 'n Spruce Resort

8/10 Good
"The facilities and property made for a wonderful family visit to the Bershires."
Jared 5-night trip
Posted 2 days ago
Holiday Inn Club Vacations Oak 'n Spruce Resort
Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South

8/10 Good
"Great location for our trip into NE."
Mark 1-night trip
Posted 2 days ago
Quality Inn Lee - Lenox South
Berkshires Untold

Berkshires Untold

8/10 Good
"Liked he cleanliness. Room was very cold and no heat was available."
Anne E 2-night trip
Posted 3 days ago
Berkshires Untold
Howard Johnson by Wyndham Saugerties

Howard Johnson by Wyndham Saugerties

8/10 Good
"Clean but the bed is ROCK hard..."
Heather 1-night trip
Posted 4 days ago
Howard Johnson by Wyndham Saugerties
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

10/10 Excellent
"Good"
Kauan 1-night trip
Posted 5 days ago
Howard Johnson by Wyndham Lenox

Frequently asked questions

What accommodations do travelers recommend in Hillsdale?
Guests like Quality Inn Great Barrington.
Can I book a refundable accommodation in Hillsdale?
If you want the flexibility to change your travel plans to Hillsdale, most hotels offer refundable* rates you can book. You can find these accommodations by searching our site and using the "fully refundable" filter to narrow the results down.
Where can I stay in Hillsdale if I want a vacation home instead of a traditional hotel?
If you want to find a good alternative to a hotel, review our selection of 45 vacation homes.
What will the weather in Hillsdale be like during my vacation?
The warmest months in Hillsdale are usually July and August with an average temp of 68°F. January and February are the chilliest months when the average temp is 29°F. The rainiest months are October and August.
Why should I book my Hillsdale accommodation with Hotels.com?
There are plenty of reasons to book your Hillsdale 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.

Keep exploring