Best Hillsdale Hotels in 2026 from HK$544 - Fully Refundable Options

A rural landscape with snow-covered fields, a winding road, and scattered trees.

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Go beyond your typical stay in Hillsdale

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Our top choices for Hillsdale hotels

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

A compact kitchen with a wooden countertop, a coffee machine, and a small shelf with a hair dryer and cups.

1. The Brooks Motel

Hillsdale

Nelson

HK$1,143

HK$1,280 total

includes taxes & fees

24 Aug - 25 Aug

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

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

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

2. Little Cat Lodge

Copake Falls

Kees

HK$1,475

HK$1,652 total

includes taxes & fees

23 Aug - 24 Aug

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

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.

An indoor swimming pool with clear water, surrounded by chairs and tables, large windows, and a tiled floor.

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

Great Barrington

BJORN

HK$902

HK$1,007 total

includes taxes & fees

20 Sept - 21 Sept

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

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.

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

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

Great Barrington

Lisa

HK$1,526

HK$1,705 total

includes taxes & fees

21 Sept - 22 Sept

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 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.

5. Quality Inn Great Barrington

Great Barrington

Sisile

HK$726

HK$811 total

includes taxes & fees

21 Sept - 22 Sept

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

A wooden cabin with a bed, a chair, and a table by a large window overlooking a lake.

A wooden wall with a white pendant light fixture.

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

6. Prospect Berkshires

Egremont

Kellee

HK$2,576

HK$3,141 total

includes taxes & fees

17 Sept - 18 Sept

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

A bar area with a green counter, two pendant lights, and shelves stocked with bottles.

7. the Alander

Copake

Jerry

HK$1,333

HK$1,493 total

includes taxes & fees

31 Aug - 1 Sept

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.

8. Wilder House Berkshires

Sheffield

Jennifer

HK$1,541

HK$1,721 total

includes taxes & fees

1 Sept - 2 Sept

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

A modern living room with a grey sofa, a wooden coffee table, and a dining area with a round table and chairs.

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

9. East Rock Inn

Great Barrington

ERIK

HK$988

HK$1,104 total

includes taxes & fees

14 Sept - 15 Sept

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

A bedroom with a wooden bed, bedside tables, a desk, and a chair.

10. Granville House

Housatonic

Nicole

HK$2,156

HK$2,408 total

includes taxes & fees

26 Aug - 27 Aug

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

A row of white plastic chairs on a covered outdoor area with a white building in the background.

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.

11. Monument Mountain Motel

Great Barrington

John

HK$670

HK$749 total

includes taxes & fees

1 Sept - 2 Sept

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

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.

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.

12. Shaker Mill Inn

West Stockbridge

Mervin

HK$1,388

HK$1,522 total

includes taxes & fees

8 Sept - 9 Sept

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

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.

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

13. Travelodge by Wyndham Great Barrington Berkshires

Great Barrington

Elspeth

HK$619

HK$692 total

includes taxes & fees

1 Sept - 2 Sept

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

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

14. The Little Lion

Great Barrington

Anne

HK$882

HK$985 total

includes taxes & fees

1 Sept - 2 Sept

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

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.

15. Quality Inn Lee - Lenox South

Lee

Christine

HK$860

HK$960 total

includes taxes & fees

21 Sept - 22 Sept

A wooden deck with a lattice railing, surrounded by lush greenery and a gravel path.

A wooden deck with a staircase leading to a porch, a white door, and hanging flower baskets.

A wooden deck with a staircase leading to a covered porch.

A cozy living room with a gray sofa, wooden ceiling beams, a black TV stand, and a dining area with a table and chairs.

16. Micosta Leisure Inn

Hudson

Andrea

HK$1,015

HK$1,137 total

includes taxes & fees

27 Aug - 28 Aug

A bedroom with a large mural of a waterfall, two bedside lamps, a bed with multiple pillows, and a nightstand with a lamp.

A traditional living room with a fireplace, floral patterned sofa, and a patterned rug.

A two-story house with a porch, a front door, and a mailbox.

A room with a white door, a window, and a wall with various framed pictures.

17. Changing Times Boutique Country Lodging

Craryville

Thomas

HK$1,568

HK$1,756 total

includes taxes & fees

31 Aug - 1 Sept

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

A bar with wooden floors and shelves filled with bottles.

18. The Red Lion Inn

Stockbridge

Patricia

HK$1,304

HK$1,847 total

includes taxes & fees

14 Sept - 15 Sept

A bedroom with a large bed, a chair, and a window with curtains.

A covered porch with a dining area, a sofa, and decorative wall art.

A large, two-story house with a porch and multiple windows, surrounded by a well-maintained lawn.

A framed painting of a white horse on a wooden dresser, a white fireplace with a black mantle, and two green vases with white flowers on the wall.

19. The White Hart

Salisbury

William

HK$2,692

HK$3,096 total

includes taxes & fees

24 Aug - 25 Aug

A modern kitchen with white cabinetry, a wooden table, and a large window providing a view of the outdoors.

A spacious living area with a wooden ceiling, a brick fireplace, and a kitchen in the background.

A spacious living area with a brick fireplace, a dining table with chairs, and a view of the outdoors.

A wooden staircase leading to a second floor, a living room with a sofa and a coffee table, and a patterned rug on the floor.

20. Charming 6 Bdrm Countryside Stay

Great Barrington

HK$2,837

HK$7,088 total

includes taxes & fees

8 Sept - 9 Sept

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Stay near popular Hillsdale attractions

Catamount Aerial Adventure Park

6.4/10 (5 reviews)

Scale New England's largest aerial adventure park with over 150 treetop challenges across nine difficulty levels. Glide between zip lines and navigate bridges while surrounded by serene forest scenery.

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Copake Lake

This glacial lake in the Hudson Valley offers pristine waters for boating, fishing, and swimming year-round. Enjoy serene morning kayaking or lively afternoons of water skiing surrounded by picturesque natural scenery.

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Hillsdale Town Hall

This historic former library now serves as Hillsdale's administrative centre with distinctive slate-shingled roof and Ionic columns. Visit during town board meetings to experience local governance.

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Mosquito Island

Commune with nature and explore the great outdoors at Mosquito Island during your travels in Copake Lake.

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Community Library

The Roeliff Jansen Community Library serves as a vital cultural hub for Hillsdale, Copake, and Ancram communities. Visitors enjoy book clubs, writing groups, and educational workshops in its welcoming atmosphere.

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Roe Jan Brewing Co.

After visiting Roe Jan Brewing Co., make a plan to see the other sights and activities in Hillsdale. Discover the sunrises while you're in the area.

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Learn more about Hillsdale

Tucked in the Hudson Valley, this rural hamlet offers scenic hikes through Taconic State Park and charming farm-to-table dining. Explore nearby art galleries in Copake or visit Catamount Mountain Resort for outdoor adventures in all seasons.

See all hotels in Hillsdale

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

Top Hillsdale Hotel Reviews

FairBridge Inn Express

10/10 Excellent

"It was very nice and everyone was extremely helpful"

Howard Johnson by Wyndham Lenox

8/10 Good

"Room was clean and comfortable. Always nice to have a frig and microwave."

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

10/10 Excellent

"Loved my stay at the little cabin, will definitely be returning."

The Yankee Inn

10/10 Excellent

"Everything was clean and well maintained. Very good included breakfast, close to Tanglewood, the Manor, the Norman Rockwell Museum, Lenox and Stockbridge."

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

10/10 Excellent

"NA"

Quality Inn Great Barrington

8/10 Good

"Only real challenge—getting on the hotel wifi was a frustrating challenge! And every time you left your room you had to get on again."

Holiday Inn & Suites Pittsfield-Berkshires by IHG

8/10 Good

"I had 2 rooms. 1 room (414) did not have a phone, the microwave didn't have power. The other room was fine. We didn't like that there was only 1 elevator working as we had to wait quite a while sometimes to go up or down. We understand that the hotel is undergoing renovations. Overall, we enjoyed our stay."

St. Charles Hotel

8/10 Good

"The place was clean and reasonably priced and perfectly located for a jaunt around Hudson. However one of the lamps in my room wasn’t functional and there was no hair dryer. Small things but noticeable. The details are small but noticeable. But I would stay there again of traveling to Hudson"

voco James Newbury Hudson Valley by IHG

8/10 Good

"Not enough staff for the breakfast , otherwise charming place. Divine beds."