𝗧𝗢𝗣 𝟭𝟬 𝗛𝗼𝘁𝗲𝗹𝘀 𝗶𝗻 Hillsdale (2026)

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

Condo

Pool

Hot tub

Cottage

Family friendly

Waterpark

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 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

S$209

includes taxes & fees

12 Oct - 13 Oct

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

2. Little Cat Lodge

Copake Falls

Kees

S$218

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

3. Quality Inn Great Barrington

Great Barrington

Joan

S$108

includes taxes & fees

1 Nov - 2 Nov

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

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.

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

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

Great Barrington

Maria Dulce

S$119

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 modern hotel lobby with a seating area, a sofa, and a large window with curtains.

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

Bruce

S$205

includes taxes & fees

2 Nov - 3 Nov

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

A motel with a parking lot and several cars parked.

6. Monument Mountain Motel

Great Barrington

Andrea

S$86

includes taxes & fees

1 Nov - 2 Nov

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

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 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

S$244

includes taxes & fees

12 Oct - 13 Oct

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

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.

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

8. Prospect Berkshires

Egremont

Conor

S$448

includes taxes & fees

10 Nov - 11 Nov

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 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.

9. Travelodge by Wyndham Great Barrington Berkshires

Great Barrington

Mark

S$113

includes taxes & fees

12 Oct - 13 Oct

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.

10. East Rock Inn

Great Barrington

ERIK

S$178

includes taxes & fees

10 Nov - 11 Nov

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.

11. The Little Lion

Great Barrington

Lidia

S$148

includes taxes & fees

18 Oct - 19 Oct

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.

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

Lee

Bob

S$168

includes taxes & fees

10 Nov - 11 Nov

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.

A modern kitchen with a coffee machine, a refrigerator, and a dining area with chairs and tables.

13. Quality Inn Lee - Lenox South

Lee

Christine

S$133

includes taxes & fees

1 Nov - 2 Nov

A wooden deck with a lattice railing, surrounded by lush greenery and a gravel path.

A wooden deck with a staircase leading to a porch, a white door, and hanging flower baskets.

A cozy living room with a gray sofa, wooden ceiling beams, a black TV stand, and a dining area with a table and chairs.

A wooden deck with a staircase leading to a covered porch.

14. Micosta Leisure Inn

Hudson

Kim

S$143

includes taxes & fees

13 Oct - 14 Oct

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

A stone fireplace with a television above it, a kitchen area to the left, and a wooden floor.

A cozy room with a bed, a sofa, a small table, and a desk. There are two lamps on the bed and a window with curtains.

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.

15. Shaker Mill Inn

West Stockbridge

Steven

S$183

includes taxes & fees

10 Nov - 11 Nov

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

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.

A small cabin with two Adirondack chairs in a grassy field, surrounded by trees and a mountain in the background.

16. Granville House

Housatonic

Marcia

S$363

includes taxes & fees

12 Oct - 13 Oct

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 covered porch with wicker furniture and hanging flower baskets.

A bar with wooden floors and shelves filled with bottles.

17. The Red Lion Inn

Stockbridge

Stephan

S$289

includes taxes & fees

3 Nov - 4 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 traditional living room with a fireplace, floral patterned sofa, and a patterned rug.

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

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

18. Changing Times Boutique Country Lodging

Craryville

Thomas

S$287

includes taxes & fees

13 Oct - 14 Oct

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

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.

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

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

South Lee

Jared

S$192

includes taxes & fees

13 Oct - 14 Oct

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.

20. The Yankee Inn

Lenox

Basil

S$152

includes taxes & fees

1 Nov - 2 Nov

View all properties

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

Holiday Inn Club Vacations Oak 'n Spruce Resort

10/10 Excellent

"The room was incredible. Just need to be a little friendly at the arrival."

Hotel On North

10/10 Excellent

"The little things, like a small extra mirror in the bathroom that has a magnifier lens."

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

10/10 Excellent

"We requested a room on the first floor in advance. When we got there there were aware and assigned us accordingly! Staff very accommodating to our questions and food inquiries"

Berkshires Untold

10/10 Excellent

"Great, we'll run hotel"

The Black Swan Lee - Lenox, an Ascend Collection Hotel

8/10 Good

"Nice motel located on Laurel Lake. Convenient location. We did not upgrade to a room with a view of lake, but should consider. Lovely breakfast with big windows on the lake. Everything worked fine, would stay again."

The Cornell Inn, Lenox & The Berkshires

10/10 Excellent

"Lovely room, comfortable bed and a nice breakfast."

The Yankee Inn

10/10 Excellent

"Although it's an older hotel, it's well maintained.Clean and updated also very friendly staff."

Pocketbook Hotel and Bath

10/10 Excellent

"Beautiful building. Glad to see it repurposed."

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!"

More cheap stays in Hillsdale

FairBridge Inn Express

16 Cheshire Road Pittsfield MA

S$76

10 Nov - 11 Nov

includes taxes & fees

Quality Inn Great Barrington

372 Main Street Great Barrington MA

S$108

1 Nov - 2 Nov

includes taxes & fees

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

1055 South Street Pittsfield MA

S$142

9 Nov - 10 Nov

includes taxes & fees

9.2/10 Wonderful! (234 reviews)

The Yankee Inn

461 Pittsfield Rd Lenox MA

S$152

1 Nov - 2 Nov

includes taxes & fees

9.2/10 Wonderful! (1,002 reviews)

St. Charles Hotel

16 Park Place Hudson NY

S$260

12 Oct - 13 Oct

includes taxes & fees

6.6/10 (990 reviews)

Pocketbook Hotel and Bath

549 Washington Street Hudson NY

S$408

1 Nov - 2 Nov

includes taxes & fees

8.6/10 Excellent! (89 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.

Explore a world of travel with Expedia

Things to do in Albany

Hillsdale Hotels from S$76

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. Quality Inn Great Barrington

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

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

6. Monument Mountain Motel

7. the Alander

8. Prospect Berkshires

9. Travelodge by Wyndham Great Barrington Berkshires

10. East Rock Inn

11. The Little Lion

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

13. Quality Inn Lee - Lenox South

14. Micosta Leisure Inn

15. Shaker Mill Inn

16. Granville House

17. The Red Lion Inn

18. Changing Times Boutique Country Lodging

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

20. 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

Holiday Inn Club Vacations Oak 'n Spruce Resort

Hotel On North

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

Berkshires Untold

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Cornell Inn, Lenox & The Berkshires

The Yankee Inn

Pocketbook Hotel and Bath

Quality Inn Lee - Lenox South

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