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

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

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Go beyond your typical stay in Hillsdale

Pet friendly

Apartment

Pool

Spa

Hot tub

Cottage

Family friendly

Waterpark

Condo

Check prices for these dates

Tonight

Tomorrow

Next weekend

In two weeks

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 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.

1. The Brooks Motel

Hillsdale

Nelson

RM595

RM666 total

includes taxes & fees

18 Oct - 19 Oct

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 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

Stacy

RM621

RM695 total

includes taxes & fees

2 Nov - 3 Nov

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 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.

3. Prospect Berkshires

Egremont

Conor

RM1,157

RM1,429 total

includes taxes & fees

10 Nov - 11 Nov

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 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.

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

Great Barrington

RM586

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 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'.

5. Quality Inn Great Barrington

Downtown Great Barrington

Scott Patterson

RM309

RM345 total

includes taxes & fees

8 Nov - 9 Nov

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

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

Great Barrington

Cynthia

RM339

RM378 total

includes taxes & fees

17 Nov - 18 Nov

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.

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

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

7. the Alander

Copake

Luis

RM571

RM640 total

includes taxes & fees

19 Oct - 20 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 large, two-story white building with a symmetrical facade, columns, and a central entrance.

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

RM1,158 total

includes taxes & fees

25 Oct - 26 Oct

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

A motel with a parking lot and several cars parked.

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.

9. Monument Mountain Motel

Great Barrington

Andrea

RM244

RM273 total

includes taxes & fees

1 Nov - 2 Nov

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

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

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.

10. Travelodge by Wyndham Great Barrington Berkshires

Great Barrington

Mark

RM322

RM360 total

includes taxes & fees

18 Oct - 19 Oct

A large house with a balcony and a grassy yard.

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.

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

RM422

RM472 total

includes taxes & fees

18 Oct - 19 Oct

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

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.

12. Wilder House Berkshires

Sheffield

Mark

RM708

RM791 total

includes taxes & fees

29 Oct - 30 Oct

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 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.

13. Courtyard by Marriott Lenox Berkshires

Lenox

Vandhana

RM513

RM573 total

includes taxes & fees

1 Nov - 2 Nov

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 covered porch with wicker furniture and hanging flower baskets.

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

14. The Red Lion Inn

Stockbridge

Stephan

RM643

RM921 total

includes taxes & fees

4 Nov - 5 Nov

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.

15. East Rock Inn

Great Barrington

Sharon

RM542

RM605 total

includes taxes & fees

4 Nov - 5 Nov

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

A modern breakfast area with a coffee machine, cereal, and bakery options.

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.

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

Saugerties

Linda

RM502

RM562 total

includes taxes & fees

15 Nov - 16 Nov

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

A covered patio with a round glass table and metal chairs, a wooden deck, and a view of trees and hills.

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.

17. Shaker Mill Inn

West Stockbridge

Steven

RM510

RM560 total

includes taxes & fees

16 Nov - 17 Nov

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

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

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

South Lee

Michael

RM478

RM613 total

includes taxes & fees

20 Oct - 21 Oct

A lakeside setting with Adirondack chairs and a covered seating area, surrounded by trees and hills in the background.

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.

A lakeside dock with kayaks and a covered boat ramp.

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

Lee

Gustavo

RM465

RM519 total

includes taxes & fees

15 Nov - 16 Nov

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

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.

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

20. Changing Times Boutique Country Lodging

Craryville

Thomas

RM816

RM914 total

includes taxes & fees

19 Oct - 20 Oct

View all properties

Hotels recommended for families in Hillsdale

The Brooks Motel

Hillsdale

RM595

RM666 total

includes taxes & fees

18 Oct - 19 Oct

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Great Barrington

RM339

RM378 total

includes taxes & fees

17 Nov - 18 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

RM586

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

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

The Yankee Inn

Lenox

RM433

RM483 total

includes taxes & fees

1 Nov - 2 Nov

Save an average of 15% on thousands of hotels when you're signed in

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.

See properties

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.

See properties

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.

See properties

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.

See properties

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.

See properties

Mosquito Island

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

See properties

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 Red Lion Inn

10/10 Excellent

"This place is a must stay! We loved every bit of it and had a best time!!! Def recommend 100%"

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 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

RM290

RM324 total

18 Oct - 19 Oct

includes taxes & fees

5.4/10 (924 reviews)

Quality Inn Great Barrington

372 Main Street Great Barrington MA

RM309

RM345 total

8 Nov - 9 Nov

includes taxes & fees

8.6/10 Excellent! (1,003 reviews)

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

1055 South Street Pittsfield MA

RM388

RM433 total

17 Nov - 18 Nov

includes taxes & fees

9.4/10 Exceptional! (238 reviews)

The Yankee Inn

461 Pittsfield Rd Lenox MA

RM433

RM483 total

1 Nov - 2 Nov

includes taxes & fees

9.2/10 Wonderful! (1,002 reviews)

St. Charles Hotel

16 Park Place Hudson NY

RM520

RM588 total

15 Nov - 16 Nov

includes taxes & fees

6.6/10 (1,000 reviews)

Pocketbook Hotel and Bath

549 Washington Street Hudson NY

RM955

RM1,264 total

15 Nov - 16 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. Travelodge by Wyndham Great Barrington Berkshires

11. The Little Lion

12. Wilder House Berkshires

13. Courtyard by Marriott Lenox Berkshires

14. The Red Lion Inn

15. East Rock Inn

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

17. Shaker Mill Inn

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

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

20. Changing Times Boutique Country Lodging

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 Red Lion Inn

Holiday Inn Club Vacations Oak 'n Spruce Resort

Berkshires Untold

The Whitlock

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

Explore a world of travel with Expedia

Go further with the Expedia app