Top 10 Hotels in Hillsdale, NY from ￥10,563 - 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 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.

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

1. The Brooks Motel

Hillsdale

Nelson

￥23,039

￥25,805 total

includes taxes & fees

Oct 25 - Oct 26

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

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

2. Little Cat Lodge

Copake Falls

Stacy

￥22,352

￥25,034 total

includes taxes & fees

Nov 17 - Nov 18

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

3. Prospect Berkshires

Egremont

Conor

￥43,195

￥53,546 total

includes taxes & fees

Nov 4 - Nov 5

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 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.

4. Quality Inn Great Barrington

Downtown Great Barrington

Scott Patterson

￥11,954

￥13,352 total

includes taxes & fees

Nov 11 - Nov 12

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.

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

Great Barrington

￥22,711

￥25,368 total

includes taxes & fees

Nov 2 - Nov 3

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

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

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

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

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

Great Barrington

Cynthia

￥13,116

￥14,650 total

includes taxes & fees

Nov 17 - Nov 18

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

7. the Alander

Copake

Luis

￥22,134

￥24,789 total

includes taxes & fees

Oct 19 - Oct 20

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

8. Monument Mountain Motel

Great Barrington

Andrea

￥9,457

￥10,563 total

includes taxes & fees

Nov 15 - Nov 16

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.

9. Travelodge by Wyndham Great Barrington Berkshires

Great Barrington

Mark

￥12,484

￥13,945 total

includes taxes & fees

Oct 21 - Oct 22

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 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.

10. The Little Lion

Great Barrington

Lidia

￥16,355

￥18,269 total

includes taxes & fees

Oct 21 - Oct 22

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

11. Granville House

Housatonic

Cynthia

￥40,157

￥44,856 total

includes taxes & fees

Oct 25 - Oct 26

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

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

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

A Holiday Inn Club Vacations sign for Oak N'Spruce Resort.

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

South Lee

Michael

￥18,488

￥23,740 total

includes taxes & fees

Oct 28 - Oct 29

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

13. East Rock Inn

Great Barrington

Sharon

￥19,001

￥21,224 total

includes taxes & fees

Nov 17 - Nov 18

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

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

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

A bar with wooden floors and shelves filled with bottles.

14. The Red Lion Inn

Stockbridge

Stephan

￥24,891

￥35,653 total

includes taxes & fees

Nov 16 - Nov 17

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.

15. Quality Inn Lee - Lenox South

Lee

Lucinda

￥14,641

￥16,355 total

includes taxes & fees

Nov 15 - Nov 16

A Holiday Inn Express hotel with a covered entrance, multiple floors, and a brick facade.

A hotel lobby with a reception desk, seating area, and a corridor leading to other rooms.

A modern lobby with a reception desk, seating area, and a dining section.

A Holiday Inn Express & Suites sign with a clear view of the hotel building in the background.

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

Saugerties

Linda

￥19,436

￥21,770 total

includes taxes & fees

Nov 15 - Nov 16

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

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

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

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

17. Courtyard by Marriott Lenox Berkshires

Lenox

Vandhana

￥19,859

￥22,183 total

includes taxes & fees

Nov 1 - Nov 2

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 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.

18. The Yankee Inn

Lenox

Basil

￥15,589

￥17,412 total

includes taxes & fees

Oct 21 - Oct 22

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

A bedroom with a large bed, a dresser, a chair, and a mirror.

19. Wilder House Berkshires

Sheffield

Mark

￥27,431

￥30,640 total

includes taxes & fees

Oct 29 - Oct 30

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 lakeside dock with kayaks and a covered boat ramp.

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

Gustavo

￥18,008

￥20,115 total

includes taxes & fees

Nov 15 - Nov 16

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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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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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Mosquito Island

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

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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 Club Vacations Oak 'n Spruce Resort

10/10 Excellent

"We were able to get rental as a last minute deal for a villa here and we're very pleased with the property. The two rooms were very spacious each with its own bathroom, one with jacuuzi. Was quiet and you don't see or hear neighbor next to you. The rooms were quite roomy. All amenities in kitchen and nice livingroom/dining area. Nice outdoor seating with table and nice view of mountains. Only issue encountered was figuring out how the showers worked, figured it out by pulling down a round lever on bottom of faucet. Very clean and spacious, nice experience."

Berkshires Untold

10/10 Excellent

"Great room and great bar. It takes time but is worth it"

The Whitlock

10/10 Excellent

"This property was the perfect location to enjoy downtown Lennox and very close to our friends’ son’s wedding at Tanglewood. I’d stay again!"

Quality Inn Great Barrington

8/10 Good

"The hotel is in a good location. There are some good restaurants within walking distance. Only one complaint is that the bathroom fan is very loud."

The Red Lion Inn

10/10 Excellent

"Good stay"

Quality Inn Lee - Lenox South

8/10 Good

"Pleasant stay, nice and clean conditions."

The Yankee Inn

10/10 Excellent

"The room and the hotel looked very clean, and the staff were very friendly. Also, the breakfast offered a good variety."

FairBridge Inn Express

10/10 Excellent

"This motel was well-cared for and a good value compared to anywhere close boy on our early-October Saturday night in the busy Berkshires!"

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

10/10 Excellent

"New hotel with clean"

More cheap stays in Hillsdale

FairBridge Inn Express

16 Cheshire Road Pittsfield MA

￥10,229

￥11,426 total

Nov 1 - Nov 2

includes taxes & fees

5.4/10 (924 reviews)

Quality Inn Great Barrington

372 Main Street Great Barrington MA

￥11,954

￥13,352 total

Nov 11 - Nov 12

includes taxes & fees

8.6/10 Excellent! (1,003 reviews)

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

1055 South Street Pittsfield MA

￥15,012

￥16,768 total

Nov 17 - Nov 18

includes taxes & fees

9.4/10 Exceptional! (238 reviews)

The Yankee Inn

461 Pittsfield Rd Lenox MA

￥15,589

￥17,412 total

Oct 21 - Oct 22

includes taxes & fees

9.2/10 Wonderful! (1,002 reviews)

St. Charles Hotel

16 Park Place Hudson NY

￥20,148

￥22,768 total

Nov 15 - Nov 16

includes taxes & fees

6.6/10 (1,000 reviews)

Pocketbook Hotel and Bath

549 Washington Street Hudson NY

￥36,976

￥48,926 total

Nov 15 - Nov 16

includes taxes & fees

8.6/10 Excellent! (91 reviews)

Frequently asked questions

Where is the best place to stay in Hillsdale?

Located 20.9 mi (33.7 km) from the heart of Hillsdale, Berkshire Mountain Lodge is a top choice for your stay based on our traveler data. Two other choices for your visit to the area are Quality Inn Great Barrington and Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy. See all available top hotels, or vacation rentals in Hillsdale.

What's the top vacation rental in Hillsdale?

Modern Luxurious Cabin, Catskills - The Tiny Nook: This vacation home rental outside of Hillsdale is located in a rural location and offers a patio, air-conditioning, and WiFi to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. See all vacation rentals in Hillsdale.

If I need to cancel my hotel reservation in Hillsdale, will I receive a refund?

Yes! You'll find that most room reservations are fully refundable if cancelled before the hotel's cancellation deadline, which is often 24 or 48 hours before the scheduled arrival. If your reservation is non-refundable, it may still be possible to cancel it and get a refund within 24 hours of booking. Filter your search by fully refundable to find flexible hotel deals in Hillsdale.

Where can I learn more about changing or cancelling my trip to Hillsdale?

To access more information about changing or cancelling your trip to Hillsdale, head over to our customer service page.

What's the best accommodation for a family vacation in Hillsdale?

Farm House Getaway on beautiful horse farm! is a country house with in-room kitchens and laundry facilities, and it's a top choice on Expedia for families. Attractions in the area like Hotchkiss Mobile Studio and Stoddard Corner are also fun for kids of all ages. Find more child-friendly accommodations in Hillsdale.

What's the best accommodation for a romantic getaway to Hillsdale?

Farm House Getaway on beautiful horse farm! is a favorite country house for couples, and features in-room fireplaces and a garden. See all romantic hotels in Hillsdale.

What's the best pet-friendly accommodation in Hillsdale?

The Brooks Motel is a top pet-friendly option for your stay. Hudson valley and The Berkshires Cottage is another option for a stay with your pet. See more pet-friendly hotel accommodations in Hillsdale.

Where is the best hotel to stay close to Catamount Aerial Adventure Park?

Catamount Lodging is one of the top choices for your stay based on our traveler data, and this aparthotel offers private balconies and free WiFi. It's located just a short 0.3 mi (0.5 km) from Catamount Aerial Adventure Park. Another good option is Holiday House Motel, located 1.2 mi (2 km) away.

What are some accommodations with pools in Hillsdale?

Berkshire Mountain Lodge: Features free self parking, an indoor pool, and complimentary wireless internet access. Pocketbook Hotel and Bath and The Yankee Inn are a couple of other choices with an onsite pool. View all hotels with pools in Hillsdale.

What is the best hotel near Albany International Airport (ALB)?

Albany Airport Inn and Suites is a popular 3-star hotel featuring free breakfast and an outdoor pool. It's located a short 1.2 mi (2 km) from Albany Intl. Airport. Other places to stay close to the airport are Hilton Garden Inn Albany Airport and Red Lion Hotel Albany.

What's it like staying in Hillsdale?

Visitors can enjoy all that Hillsdale has to offer including the coffeehouses and ski areas. This city also attracts tourists with its relaxing and quaint setting. In Hillsdale, there are 59 hotels and other accommodations to choose from. Find out more about Hillsdale.

What should I do while I'm visiting Hillsdale?

The picturesque setting of Copake Lake and Mosquito Island exemplify the area's natural beauty. A couple of additional sights to add to your agenda are Catamount Aerial Adventure Park and Catamount Ski Area. Check out what more to see and do in Expedia's Hillsdale guide.

What's the weather like in Hillsdale?

The hottest months are usually July and August with an average temp of 68°F, while the coldest months are January and February with an average of 29°F. The snowiest months in Hillsdale are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.

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Find hotels in Hillsdale, NY from ￥10,563

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Hillsdale

Check prices for these dates

Filter by

Property class

Guest rating

Our top choices for Hillsdale hotels

1. The Brooks Motel

2. Little Cat Lodge

3. Prospect Berkshires

4. Quality Inn Great Barrington

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

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

7. the Alander

8. Monument Mountain Motel

9. Travelodge by Wyndham Great Barrington Berkshires

10. The Little Lion

11. Granville House

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

13. East Rock Inn

14. The Red Lion Inn

15. Quality Inn Lee - Lenox South

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

17. Courtyard by Marriott Lenox Berkshires

18. The Yankee Inn

19. Wilder House Berkshires

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

Stay near popular Hillsdale attractions

Catamount Aerial Adventure Park

Copake Lake

Hillsdale Town Hall

Community Library

Roe Jan Brewing Co.

Mosquito Island

Learn more about Hillsdale

Top Hillsdale Hotel Reviews

Holiday Inn Club Vacations Oak 'n Spruce Resort

Berkshires Untold

The Whitlock

Quality Inn Great Barrington

The Red Lion Inn

Quality Inn Lee - Lenox South

The Yankee Inn

FairBridge Inn Express

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

More cheap stays in Hillsdale

FairBridge Inn Express

Quality Inn Great Barrington

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

The Yankee Inn

St. Charles Hotel

Pocketbook Hotel and Bath

Frequently asked questions

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