Hotels in Hillsdale

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Top 5 hotels in Hillsdale at a glance

1. The Brooks Motel — 2-star hotel in Hillsdale. Guest rating: 7.4/10 — Good.
2. Little Cat Lodge — 2-star hotel in Copake Falls. Guest rating: 9.8/10 — Exceptional.
3. Quality Inn Great Barrington — 2.5-star hotel in Great Barrington. Guest rating: 8.6/10 — Excellent.
4. Holiday Inn Express Hotel & Suites Great Barrington by IHG — 2.5-star hotel in Great Barrington. Guest rating: 8.8/10 — Excellent.
5. the Alander — 2.5-star hotel in Copake. Guest rating: 9.0/10 — Wonderful.

Where to stay in Hillsdale?

A modern bedroom with a large bed, two bedside tables, and a textured wall behind the bed.

A dining area with a wooden table, chairs, and a colorful striped rug.

A snow-covered landscape with a house and a sign that reads "the brooks".

A living room with a sofa, a coffee table, a fireplace, and a ceiling fan.

1. The Brooks Motel

Hillsdale

$146

$163 total

includes taxes & fees

Sep 3 - Sep 4

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 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.

2. Little Cat Lodge

Copake Falls

$199

$223 total

includes taxes & fees

Sep 7 - Sep 8

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

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

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

Great Barrington

$93

$103 total

includes taxes & fees

Sep 22 - Sep 23

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

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

A Holiday Inn Express & Suites building with a clear entrance, a covered parking area, and a stone facade.

An indoor swimming pool with a 6 feet 18 meters depth, surrounded by chairs and tables, with large windows offering views of trees.

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

Great Barrington

$111

$124 total

includes taxes & fees

Sep 7 - Sep 8

A modern building with a dark exterior, outdoor seating area with wooden chairs, and string lights.

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 dining table set with plates of food, wine glasses, and bottles, with a chandelier above and shelves above holding glasses and bottles.

A dog standing at a door entrance with a wooden floor and a mat with paw prints.

5. the Alander

Copake

$145

$162 total

includes taxes & fees

Sep 7 - Sep 8

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

A motel with a parking lot and several cars parked.

6. Monument Mountain Motel

Great Barrington

$95

$106 total

includes taxes & fees

Sep 7 - Sep 8

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

A corner market with a sign reading "the Corner Market" and shelves stocked with various snacks and groceries.

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

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

Great Barrington

$161

$179 total

includes taxes & fees

Sep 7 - Sep 8

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

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

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

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

8. Travelodge by Wyndham Great Barrington Berkshires

Great Barrington

$85

$95 total

includes taxes & fees

Sep 7 - Sep 8

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.

9. East Rock Inn

Great Barrington

$141

$157 total

includes taxes & fees

Sep 22 - Sep 23

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.

10. Prospect Berkshires

Egremont

$365

$441 total

includes taxes & fees

Sep 7 - Sep 8

A large house with a balcony and a grassy yard.

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

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

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.

11. The Little Lion

Great Barrington

$125

$140 total

includes taxes & fees

Sep 3 - Sep 4

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

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

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

12. The Yankee Inn

Lenox

$100

$112 total

includes taxes & fees

Sep 28 - Sep 29

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

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

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

A cozy living room with a sofa, a small table, and a bookshelf. There is a window with curtains, and a painting on the wall.

13. Shaker Mill Inn

West Stockbridge

$160

$176 total

includes taxes & fees

Sep 8 - Sep 9

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

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

A modern kitchen with a coffee machine, a refrigerator, and a dining area with chairs and tables.

14. Quality Inn Lee - Lenox South

Lee

$110

$122 total

includes taxes & fees

Sep 22 - Sep 23

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.

15. Wilder House Berkshires

Sheffield

$223

$249 total

includes taxes & fees

Sep 10 - Sep 11

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

A bar with wooden floors and shelves filled with bottles.

A covered porch with wicker furniture and hanging flower baskets.

A backyard with a swimming pool, lounge chairs, and a hot tub.

16. The Red Lion Inn

Stockbridge

$167

$237 total

includes taxes & fees

Sep 30 - Oct 1

17. Berkshire Travel Lodge

Austerlitz

$75

$84 total

includes taxes & fees

Sep 13 - Sep 14

A dining table with pastries, a coffee pot, and a vase of sunflowers.

A pool table in a room with a patterned rug, a shelf with decorative items, and a window with a view of greenery.

A large, two-story white building with a symmetrical facade, columns, and a central entrance.

A small cabin with two Adirondack chairs in a grassy field, surrounded by trees and a mountain in the background.

18. Granville House

Housatonic

$275

$307 total

includes taxes & fees

Sep 3 - Sep 4

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 multi-story building with a symmetrical facade, multiple balconies, and a central tower.

An indoor swimming pool with clear water, a lifeguard station, and a sign indicating no lifeguard on duty.

19. Holiday Inn Club Vacations Oak 'n Spruce Resort

South Lee

$103

$134 total

includes taxes & fees

Sep 7 - Sep 8

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

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.

A lodge with a large building and a dock by a lake, surrounded by forest.

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

Lee

$128

$142 total

includes taxes & fees

Sep 23 - Sep 24

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Go beyond your typical stay in Hillsdale

Pet friendly

Pool

Spa

Hot tub

Cottage

Family friendly

Our prices for hotels in Hillsdale are cheapest in April

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.

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Copake Lake

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

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Hillsdale Town Hall

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

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Mosquito Island

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

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Community Library

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

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Roe Jan Brewing Co.

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

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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 Copake Lake and Hillsdale Town Hall 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

Quality Inn Great Barrington

10/10 Excellent

"Staff at the front desk were welcoming, friendly, and helpful throughout my stay. The room was very clean. The bed was comfortable. The shower had good water pressure and plenty of hot water. The room was equipped with a refrigerator, microwave, and coffeemaker, as well as a TV, and the WiFi worked fine. The breakfast area in the office building had several tables, and included a "make-your-own-waffles" station (love that!), buffet-style scrambled eggs and sausage, as well pre-packaged muffins. Yogurt and other items were available in a refrigerator. Parking was in a a space right outside the room entrance on the first floor, which was ground level. The location is on Main Street (Route 7) in Great Barrington, but set back from the road so there's less traffic noise. There are restaurants and shops in easy walking distance of this motel, and it is an easy drive of 15 mins. or so to the nearby towns of Lenox, Lee (location of Mass. Turnpike exit/entrance), West Stockbridge, and Stockbridge that have their own shops, restaurants, sites, and venues of interest. I highly recommend this motel."

The Red Lion Inn

10/10 Excellent

"this grand old hotel is warm and welcoming — a real hub of Bershires life and history"

Berkshire Mountain Lodge

8/10 Good

"Clean rooms.."

Berkshires Untold

10/10 Excellent

"The entry , bar, and dining room along with the outside patio was beautifully done. It made you happy to be there as it was so welcoming. Ample parking space, great amenities, and comfy quiet room made our stay great. The only thing missing was a floor lamp in our room so we couldn’t read at night as the small lamps were dim."

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

10/10 Excellent

"Breakfast was the weakest thing, but it was free, loved the hot tub and having a couch in our room"

Pocketbook Hotel and Bath

10/10 Excellent

"It's rare to find a place that entices you to stay put because the room is so comfortable, the food is delicious, the staff is warm and inviting, and because the amenities (the baths!) are plentiful. We had a fantastic stay and will be back again!"

Howard Johnson by Wyndham Saugerties

8/10 Good

"Clean comfortable room and restaurant."

Hotel On North

8/10 Good

"Nice room! Comfortable bed. Super friendly staff."

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent

"We had a fantastic stay at the Black Swan Inn in Lee, MA. Our room was incredibly clean, comfortable, and featured a beautiful view of the lake. Both check-in and check-out were completely hassle-free .A special shoutout goes to Carrie, the breakfast attendant! The breakfast area was exceptionally clean and well-stocked thanks to her hard work. Carrie was not only helpful, pleasant, and polite, but she also worked tirelessly to ensure all food items were fresh and fully available. Her excellent service truly made our mornings. We highly recommend this inn!"

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 46 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.

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More ways to book

Book Hotels in Hillsdale on Hotels.com

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

Top 5 hotels in Hillsdale at a glance

Where to stay in Hillsdale?

1. The Brooks Motel

2. Little Cat Lodge

3. Quality Inn Great Barrington

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

5. the Alander

6. Monument Mountain Motel

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

8. Travelodge by Wyndham Great Barrington Berkshires

9. East Rock Inn

10. Prospect Berkshires

11. The Little Lion

12. The Yankee Inn

13. Shaker Mill Inn

14. Quality Inn Lee - Lenox South

15. Wilder House Berkshires

16. The Red Lion Inn

17. Berkshire Travel Lodge

18. Granville House

19. Holiday Inn Club Vacations Oak 'n Spruce Resort

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

Go beyond your typical stay in Hillsdale

Price trends for hotels in Hillsdale

Typical weather for Hillsdale

Top landmarks in Hillsdale

Catamount Aerial Adventure Park

Copake Lake

Hillsdale Town Hall

Mosquito Island

Community Library

Roe Jan Brewing Co.

Learn more about Hillsdale

Check out reviews of Hillsdale hotels guests love

Quality Inn Great Barrington

The Red Lion Inn

Berkshire Mountain Lodge

Berkshires Untold

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

Pocketbook Hotel and Bath

Howard Johnson by Wyndham Saugerties

Hotel On North

The Black Swan Lee - Lenox, an Ascend Collection Hotel

Frequently asked questions

Keep exploring