Top 10 Hotels in Hillsdale, NY from ￥10,186 - 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 dining area with a wooden table, chairs, and a colorful striped rug.

1. The Brooks Motel

Hillsdale

Nelson

￥23,023

￥25,786 total

includes taxes & fees

Oct 8 - Oct 9

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

￥24,018

￥26,901 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

￥49,031

￥60,059 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 bathroom, a bed, a desk, and a nightstand.

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

4. Quality Inn Great Barrington

Great Barrington

Joan

￥12,053

￥13,464 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 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.

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

￥22,723

￥25,382 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 kitchenette with a microwave, coffee maker, and coffee cups.

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

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

Great Barrington

Maria Dulce

￥16,107

￥17,991 total

includes taxes & fees

Oct 25 - Oct 26

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

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

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

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

7. the Alander

Copake

Thomas

￥22,818

￥25,554 total

includes taxes & fees

Oct 12 - Oct 13

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

￥9,451

￥10,556 total

includes taxes & fees

Nov 1 - Nov 2

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

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

9. Granville House

Housatonic

Marcia

￥40,109

￥44,802 total

includes taxes & fees

Oct 12 - Oct 13

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

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

10. The Red Lion Inn

Stockbridge

Stephan

￥24,917

￥35,692 total

includes taxes & fees

Nov 3 - Nov 4

A large house with a balcony and a grassy yard.

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

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.

11. The Little Lion

Great Barrington

Lidia

￥16,344

￥18,257 total

includes taxes & fees

Oct 18 - Oct 19

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.

12. Travelodge by Wyndham Great Barrington Berkshires

Great Barrington

Mark

￥12,475

￥13,934 total

includes taxes & fees

Oct 18 - Oct 19

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

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

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

13. East Rock Inn

Great Barrington

ERIK

￥22,787

￥25,454 total

includes taxes & fees

Nov 7 - Nov 8

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.

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

14. Quality Inn Lee - Lenox South

Lee

Christine

￥14,630

￥16,342 total

includes taxes & fees

Nov 1 - Nov 2

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 lakeside lodge with a dock, fishing rods, and outdoor seating.

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

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

Lee

Bob

￥18,254

￥20,389 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 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.

A hotel room with a four-poster bed, two armchairs, a small table with a book, and a decorative canopy.

16. The Yankee Inn

Lenox

William

￥16,738

￥18,697 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.

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

A large, multi-story hotel with a symmetrical facade, multiple balconies, and a well-lit entrance.

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

17. Courtyard by Marriott Lenox Berkshires

Lenox

Tracy

￥19,835

￥22,155 total

includes taxes & fees

Nov 1 - Nov 2

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

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.

A dining area with yellow chairs and tables, a kitchen in the background, and a clock on the wall.

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

18. The White Hart

Salisbury

William

￥115,235

￥132,520 total

includes taxes & fees

Oct 24 - Oct 25

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

A cozy living room with a fireplace, a bookshelf, a coffee table with a book, and a plaid sofa.

19. Wilder House Berkshires

Sheffield

Mark

￥33,882

￥37,847 total

includes taxes & fees

Oct 18 - Oct 19

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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

Berkshire Mountain Lodge

10/10 Excellent

"Very spacious and inviting..Loved the coffee maker in lobby!!!! All the girls at the front desk were extremely nice and welcoming. Very clean property and great location.. to Great Barrington, Lenox, Stockbridge, and Lee with great restaurants near by in those towns as well"

Quality Inn Lee - Lenox South

8/10 Good

"Wonderful location. Nearby Norman Rockwell museum. Perfect for a stopover."

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!"

Holiday Inn Club Vacations Oak 'n Spruce Resort

10/10 Excellent

"Went here for our 24th Wedding Anniversary!! We picked the area so we could go to the Norman Rockwell museum. To our surprise we were upgraded to a Villa. Thank you so much Becky for the accommodations. We will be back!"

The Cornell Inn, Lenox & The Berkshires

10/10 Excellent

"Delightful and charming! When you go to an inn that is over 200 years old you don’t know what to expect and everything was a wonderful surprise. Super clean, stylish, and staff that was warm and friendly. We had what we believe was the smallest room in the Inn, not much over 100 ft.², and it was perfect for a one night stay. The breakfast options were a real treat!"

Pocketbook Hotel and Bath

8/10 Good

"."

Hotel On North

10/10 Excellent

"Beautiful boutique hotel. We will be back!"

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."

More cheap stays in Hillsdale

FairBridge Inn Express

16 Cheshire Road Pittsfield MA

￥9,120

￥10,186 total

Oct 20 - Oct 21

includes taxes & fees

Quality Inn Great Barrington

372 Main Street Great Barrington MA

￥12,053

￥13,464 total

Nov 1 - Nov 2

includes taxes & fees

8.6/10 Excellent! (1,000 reviews)

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

1055 South Street Pittsfield MA

￥16,265

￥18,168 total

Nov 4 - Nov 5

includes taxes & fees

The Yankee Inn

461 Pittsfield Rd Lenox MA

￥16,738

￥18,697 total

Nov 1 - Nov 2

includes taxes & fees

9.2/10 Wonderful! (1,007 reviews)

St. Charles Hotel

16 Park Place Hudson NY

￥23,727

￥26,812 total

Oct 12 - Oct 13

includes taxes & fees

6.6/10 (990 reviews)

Pocketbook Hotel and Bath

549 Washington Street Hudson NY

￥31,912

￥43,211 total

Nov 1 - Nov 2

includes taxes & fees

8.6/10 Excellent! (87 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 ￥10,186

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. Granville House

10. The Red Lion Inn

11. The Little Lion

12. Travelodge by Wyndham Great Barrington Berkshires

13. East Rock Inn

14. Quality Inn Lee - Lenox South

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

16. The Yankee Inn

17. Courtyard by Marriott Lenox Berkshires

18. The White Hart

19. Wilder House Berkshires

Stay near popular Hillsdale attractions

Catamount Aerial Adventure Park

Copake Lake

Hillsdale Town Hall

Community Library

Mosquito Island

Roe Jan Brewing Co.

Learn more about Hillsdale

Top Hillsdale Hotel Reviews

Berkshire Mountain Lodge

Quality Inn Lee - Lenox South

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

The Red Lion Inn

Holiday Inn Club Vacations Oak 'n Spruce Resort

The Cornell Inn, Lenox & The Berkshires

Pocketbook Hotel and Bath

Hotel On North

St. Charles Hotel

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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