Top 10 Hotels in Hillsdale, NY from ￥9,974 - Competitive Prices

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

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

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

Nelson

￥22,780

￥25,516 total

includes taxes & fees

Nov 2 - Nov 3

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 house with a stone patio and wooden stools.

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

2. Little Cat Lodge

Copake Falls

Kees

￥24,059

￥26,945 total

includes taxes & fees

Nov 2 - Nov 3

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

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

3. Prospect Berkshires

Egremont

Conor

￥49,059

￥60,094 total

includes taxes & fees

Nov 2 - Nov 3

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 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.

4. Quality Inn Great Barrington

Great Barrington

Joan

￥11,973

￥13,373 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 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.

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

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

Great Barrington

Bruce

￥22,697

￥25,351 total

includes taxes & fees

Nov 2 - Nov 3

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

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

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

6. the Alander

Copake

Thomas

￥22,831

￥25,571 total

includes taxes & fees

Oct 21 - Oct 22

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

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

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

Great Barrington

Maria Dulce

￥15,642

￥17,473 total

includes taxes & fees

Nov 8 - Nov 9

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

A motel with a parking lot and several cars parked.

8. Monument Mountain Motel

Great Barrington

Andrea

￥9,456

￥10,562 total

includes taxes & fees

Nov 5 - Nov 6

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.

9. Granville House

Housatonic

Marcia

￥40,132

￥44,828 total

includes taxes & fees

Oct 12 - Oct 13

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.

10. East Rock Inn

Great Barrington

ERIK

￥21,481

￥23,994 total

includes taxes & fees

Nov 8 - Nov 9

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

A covered porch with wicker furniture and hanging flower baskets.

A bar with wooden floors and shelves filled with bottles.

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

11. The Red Lion Inn

Stockbridge

Stephan

￥24,888

￥35,649 total

includes taxes & fees

Nov 8 - Nov 9

A large house with a balcony and a grassy yard.

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

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.

12. The Little Lion

Great Barrington

Lidia

￥16,353

￥18,267 total

includes taxes & fees

Oct 21 - Oct 22

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 circular pool with a tiled edge, surrounded by a concrete deck and a grassy area with chairs and a small shed.

13. Travelodge by Wyndham Great Barrington Berkshires

Great Barrington

Mark

￥12,482

￥13,943 total

includes taxes & fees

Oct 21 - Oct 22

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.

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

14. Quality Inn Lee - Lenox South

Lee

Christine

￥14,639

￥16,353 total

includes taxes & fees

Nov 8 - Nov 9

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 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.

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

Lee

Bob

￥18,802

￥21,001 total

includes taxes & fees

Nov 2 - Nov 3

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

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

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

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

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

South Lee

Jared

￥18,486

￥23,738 total

includes taxes & fees

Oct 12 - Oct 13

17. Holiday Inn Express & Suites Saugerties - Hudson Valley by IHG

Saugerties

Cindy

￥20,066

￥22,472 total

includes taxes & fees

Nov 8 - Nov 9

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

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

18. The Yankee Inn

Lenox

William

￥16,748

￥18,708 total

includes taxes & fees

Nov 1 - Nov 2

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

A covered outdoor area with stone pillars and a view of a road and green hills.

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.

19. Courtyard by Marriott Lenox Berkshires

Lenox

Tracy

￥19,846

￥22,167 total

includes taxes & fees

Nov 1 - Nov 2

A balcony with a table featuring a bottle, glasses, and binoculars, overlooking a river, greenery, and a house.

A dining area with a brick fireplace, wooden beams, and a chandelier.

A historic hotel with a prominent tower and a brick facade.

20. Diamond Mills Resort

Saugerties

￥41,993

￥50,982 total

includes taxes & fees

Oct 12 - Oct 13

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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 center with distinctive slate-shingled roof and Ionic columns. Visit during town board meetings to experience local governance.

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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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Mosquito Island

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

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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

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

10/10 Excellent

"This hotel was clean and in a good location. The staff was friendly and helpful. I loved their nice pool and jacuzzi and enjoyed it. Breakfast was OK. Rooms are clean and big enough to make your money worth for it. One more important thing for us was its free and big parking lot."

Quality Inn Lee - Lenox South

10/10 Excellent

"My wife and I were touring the Berkshires near the end of a long road trip. We’re so glad we chose this Quality Inn in Lee for our stay! Staff in the afternoon/evening, at breakfast, and at the morning desk were all professional, friendly, and helpful. Our room was very clean and comfortable, and the amenities worked well. The continental breakfast included not only stations for waffles and toast, it also included tasty Jimmy Dean breakfast sandwiches to microwave. Coffee and tea and hot chocolate were available 24/7. Art related to nature and the Berkshires was on the walls. A highly recommended property!"

The Yankee Inn

10/10 Excellent

"Not enough bath clothes towels not enough outlets around the bed for people who have cpap or breathing problems."

The Cornell Inn, Lenox & The Berkshires

8/10 Good

"Nice Inn/B&B in Lenox MA, about a mile from downtown."

Pocketbook Hotel and Bath

10/10 Excellent

"The room and property is clean, staffs are friendly. But the old warehouse structure makes it not the best sound proof, you can hear every steps from the upstairs. Overall a great experience, highly recommended!"

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

10/10 Excellent

"Nice little cabin, well situated to sightseeing"

The Red Lion Inn

8/10 Good

"Would go there again but would request to be in the main Inn, they have properties all over the town center that are considered the Inn. That was disappointing. A very unique property and super cute!"

St. Charles Hotel

8/10 Good

"The St. Charles hotel is a good place to stay if you are looking for a great location to stay. It's within walking distance of restaurants and close to places to visit. However the WiFi network does kick out a lot."

Quality Inn Great Barrington

8/10 Good

"The staff was very pleasant and helpful. Breakfast was good. They had delicious and fresh muffins. Parking was right outside our door."

More cheap stays in Hillsdale

FairBridge Inn Express

16 Cheshire Road Pittsfield MA

￥8,929

￥9,974 total

Nov 1 - Nov 2

includes taxes & fees

5.4/10 (918 reviews)

Quality Inn Great Barrington

372 Main Street Great Barrington MA

￥11,973

￥13,373 total

Nov 1 - Nov 2

includes taxes & fees