𝗧𝗢𝗣 𝗛𝗼𝘁𝗲𝗹𝘀 𝗶𝗻 Hillsdale from RM273 (2026) - Fully Refundable Options

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

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

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

1. The Brooks Motel

Hillsdale

Nelson

RM595

RM667 total

includes taxes & fees

4 Nov - 5 Nov

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

A house with a stone patio and wooden stools.

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

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

Stacy

RM621

RM696 total

includes taxes & fees

2 Nov - 3 Nov

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

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

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

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

3. Prospect Berkshires

Egremont

Conor

RM1,158

RM1,430 total

includes taxes & fees

10 Nov - 11 Nov

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.

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.

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

Great Barrington

Kelly

RM587

RM655 total

includes taxes & fees

2 Nov - 3 Nov

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 bathroom, a bed, a desk, and a nightstand.

A Quality Inn sign, a brick building, and a parking lot with cars.

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

5. Quality Inn Great Barrington

Downtown Great Barrington

Joan

RM317

RM354 total

includes taxes & fees

10 Nov - 11 Nov

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

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

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

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

RM339

RM379 total

includes taxes & fees

10 Nov - 11 Nov

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 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.

7. the Alander

Copake

Joseph

RM694

RM778 total

includes taxes & fees

26 Oct - 27 Oct

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

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

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.

8. Granville House

Housatonic

Cynthia

RM1,037

RM1,159 total

includes taxes & fees

18 Oct - 19 Oct

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 motel with a parking lot and several cars parked.

A row of motel rooms with red doors, a covered walkway, and a view of mountains in the background.

9. Monument Mountain Motel

Great Barrington

Andrea

RM244

RM273 total

includes taxes & fees

1 Nov - 2 Nov

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.

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

10. East Rock Inn

Great Barrington

ERIK

RM584

RM652 total

includes taxes & fees

13 Nov - 14 Nov

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 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.

11. Travelodge by Wyndham Great Barrington Berkshires

Great Barrington

Mark

RM323

RM360 total

includes taxes & fees

15 Oct - 16 Oct

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.

12. Wilder House Berkshires

Sheffield

Mark

RM765

RM854 total

includes taxes & fees

26 Oct - 27 Oct

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.

13. The Little Lion

Great Barrington

Lidia

RM423

RM472 total

includes taxes & fees

18 Oct - 19 Oct

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 fire pit with two Adirondack chairs, a table with drinks, and a house in the background.

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

14. Changing Times Boutique Country Lodging

Craryville

Thomas

RM817

RM915 total

includes taxes & fees

14 Oct - 15 Oct

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 bar with wooden floors and shelves filled with bottles.

A covered porch with wicker furniture and hanging flower baskets.

15. The Red Lion Inn

Stockbridge

Stephan

RM643

RM922 total

includes taxes & fees

3 Nov - 4 Nov

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

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

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.

16. Courtyard by Marriott Lenox Berkshires

Lenox

Tracy

RM513

RM573 total

includes taxes & fees

1 Nov - 2 Nov

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 dining area with large windows, wooden furniture, and a view of a lake.

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

Lee

RM469

RM523 total

includes taxes & fees

8 Nov - 9 Nov

An indoor swimming pool with a concrete floor, a large window, and a vase with flowers.

A spacious bedroom with a large bed, a wooden headboard, a bedside table with a book and a glass, and a window with curtains.

A spacious room with leather seating, large windows, and exposed brick walls.

A restaurant with long tables, chairs, and a brick wall.

18. Pocketbook Hotel and Bath

Hudson

Vivien

RM989

RM1,302 total

includes taxes & fees

2 Nov - 3 Nov

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

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

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

Saugerties

Linda

RM519

RM581 total

includes taxes & fees

11 Nov - 12 Nov

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

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

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

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

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

South Lee

Jared

RM478

RM614 total

includes taxes & fees

28 Oct - 29 Oct

View all properties

Hotels recommended for families in Hillsdale

The Brooks Motel

Hillsdale

RM595

RM667 total

includes taxes & fees

4 Nov - 5 Nov

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Great Barrington

RM339

RM379 total

includes taxes & fees

10 Nov - 11 Nov

Monument Mountain Motel

Great Barrington

RM244

RM273 total

includes taxes & fees

1 Nov - 2 Nov

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Great Barrington

RM587

RM655 total

includes taxes & fees

2 Nov - 3 Nov

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 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.

The Yankee Inn

Lenox

RM433

RM484 total

includes taxes & fees

1 Nov - 2 Nov

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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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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

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent

"A wonderful stay not far away on a lake in the Berkshires with a copious breakfast buffet. The staff is very professional, helpful, delightful. Spectacular natural surroundings, cultural activities, and great restaurants make for a wonderful getaway. We didn't see beavers, but we did see fishermen catching nice sized trout... and Momma black bear and two cubs on a back road! Gifts from nature!"

Berkshire Mountain Lodge

8/10 Good

"We really enjoyed our stay at Berkshire Mountain Lodge. For what we paid - we absolutely feel like we got a great bang for our buck. The hotel is clean and well-maintained, and our suite was massive. It included a kitchen with all the bells and whistles (stove/stovetop, microwave, refrigerator, dishwasher), a full size living room, separate bedroom (with a kingsize mattress), and spacious bathroom. It was so comfortable. We absolutely recommend staying here, especially if you're looking for a reasonably priced accommodation."

Quality Inn Lee - Lenox South

10/10 Excellent

"The rooms were clean and parking what’s convenient."

Hotel On North

10/10 Excellent

"This is a great hotel.. likely the best place to stay in Pittsfield. Just an overnight stop so not time to get a good read on the area but a good option for the Berkshires if you you don't want to pay the Lenox/Stockbridge premium."

The Yankee Inn

8/10 Good

"Everything at the Yankee Inn was very good with the exception of, wasn’t the most comfortable bed I’ve ever slept in, but everything else was very good"

The Cornell Inn, Lenox & The Berkshires

10/10 Excellent

"It's a perfect stop on our little Berkshires trip. The Inn had everything we needed and more. The property was beautiful, and the staff was beyond helpful. We will certainly be back."

The Red Lion Inn

8/10 Good

"We had a nice stay at the Red Lion Inn. Our room was clean and had a fireplace, but did not have a mini-refrigerator and the TV was placed to the side of the bed. The restaurant charged a lot ($65 for a filet mignon entree) and the food was not up to that price. The bread and salad were a la carte. The whole place seemed in need of a refresh."

Berkshires Untold

8/10 Good

"First this is a gorgeous property, the outdoor areas are wonderful, with comfy furniture, flowers and fire pits. The main area is an intimate restaurant and bar, with a seating area with books and plants. We enjoyed drinks and dinner there and it was excellent, particularly with the sunset and fire pit to begin our evening, Absolutely lovely! Upon checking in, we were assigned a “premium” room, which sounded great, however it turned out to be on the second floor, at the end of a very long outside corridor, parking and lobby quite distant. They have no elevator. We did lug our bags and a cooler to the room, which was lovely, but we knew we would be much more comfortable on the first floor closer to the lobby, as we are somewhat older. We asked to be moved, and we accommodated, found the room the same, but lacking the coffee service and luggage rack. We were brought a luggage rack, and complimentary coffee was available in the lobby in the morning, but it seemed odd that those would be considered premium in such a nice place. The star of the place is the beautiful outdoor space, and restaurant, we just loved that!"

FairBridge Inn Express

8/10 Good

"Room was clean . Overall property was average but expected for the price"

More cheap stays in Hillsdale

FairBridge Inn Express

16 Cheshire Road Pittsfield MA

RM254

RM283 total

15 Oct - 16 Oct

includes taxes & fees

5.4/10 (923 reviews)

Quality Inn Great Barrington

372 Main Street Great Barrington MA

RM317

RM354 total

10 Nov - 11 Nov

includes taxes & fees

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

1055 South Street Pittsfield MA

RM404

RM452 total

10 Nov - 11 Nov

includes taxes & fees

The Yankee Inn

461 Pittsfield Rd Lenox MA

RM433

RM484 total

1 Nov - 2 Nov

includes taxes & fees

9.2/10 Wonderful! (1,006 reviews)

St. Charles Hotel

16 Park Place Hudson NY

RM735

RM831 total

19 Oct - 20 Oct

includes taxes & fees

6.6/10 (996 reviews)

Pocketbook Hotel and Bath

549 Washington Street Hudson NY

RM989

RM1,302 total

2 Nov - 3 Nov

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 traveller data. Two other options for your trip 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.

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

Yes! Most hotel reservations are refundable provided that you cancel prior to the hotel's cancellation deadline, which is often 24 or 48 hours before check in. If you have a non-refundable reservation, you might be able to still cancel and be given a refund within a 24-hour period of booking. Filter your search by fully refundable to find flexible hotel deals in Hillsdale.

What's the best dog-friendly place to stay in Hillsdale?

The Brooks Motel is a top dog-friendly option for your stay. See more pet-friendly hotel accommodations in Hillsdale.

What are some accommodation options 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 that feature an on-site pool. View all hotels with pools in Hillsdale.

What's it like staying in Hillsdale?

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

What should I see while I'm in 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 itinerary are Catamount Aerial Adventure Park and Catamount Ski Area. Take a look at what more there is to see and do in Expedia's Hillsdale guide.

What's the seasonal weather in Hillsdale?

The hottest months are usually July and August, with an average temperature of 20°C, while the coldest months are January and February, with an average of -1°C. The snowiest months in Hillsdale are January, March, February and November, with each month seeing an average of 18 cm of snowfall.

Hillsdale hotels from RM273

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Hillsdale

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Hillsdale hotels

1. The Brooks Motel

2. Little Cat Lodge

3. Prospect Berkshires

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

5. Quality Inn Great Barrington

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

7. the Alander

8. Granville House

9. Monument Mountain Motel

10. East Rock Inn

11. Travelodge by Wyndham Great Barrington Berkshires

12. Wilder House Berkshires

13. The Little Lion

14. Changing Times Boutique Country Lodging

15. The Red Lion Inn

16. Courtyard by Marriott Lenox Berkshires

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

18. Pocketbook Hotel and Bath

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

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

Hotels recommended for families in Hillsdale

The Brooks Motel

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Monument Mountain Motel

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

The Yankee Inn

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

The Black Swan Lee - Lenox, an Ascend Collection Hotel

Berkshire Mountain Lodge

Quality Inn Lee - Lenox South

Hotel On North

The Yankee Inn

The Cornell Inn, Lenox & The Berkshires

The Red Lion Inn

Berkshires Untold

FairBridge Inn Express

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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