Hillsdale Hotels from €59 - Fully Refundable Options

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

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Go beyond your typical stay in Hillsdale

Pet friendly

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Hot tub

Pool

Spa

Cottage

Cabin

Farm

Waterpark

Family friendly

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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 dining area with a wooden table, chairs, and a colorful striped rug.

1. The Brooks Motel

Hillsdale

Nelson

€140

includes taxes & fees

26 Aug - 27 Aug

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

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

A house with a stone patio and wooden stools.

2. Little Cat Lodge

Copake Falls

Kees

€189

includes taxes & fees

26 Aug - 27 Aug

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 reception area with framed artwork, a coffee machine, and a sign indicating 'Quality by Choice Hotels'.

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

3. Quality Inn Great Barrington

Great Barrington

Sisile

€89

includes taxes & fees

23 Sept - 24 Sept

A Holiday Inn Express & Suites building with a stone facade, a covered entrance, and a parking lot.

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

An indoor swimming pool with clear water, surrounded by chairs and tables, large windows, and a tiled floor.

A buffet with labeled containers for omelets and other dishes.

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

Great Barrington

BJORN

€118

includes taxes & fees

23 Sept - 24 Sept

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.

5. Monument Mountain Motel

Great Barrington

John

€82

includes taxes & fees

1 Sept - 2 Sept

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

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.

6. the Alander

Copake

Tom

€163

includes taxes & fees

30 Aug - 31 Aug

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

7. Travelodge by Wyndham Great Barrington Berkshires

Great Barrington

Elspeth

€76

includes taxes & fees

1 Sept - 2 Sept

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 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.

8. East Rock Inn

Great Barrington

ERIK

€121

includes taxes & fees

14 Sept - 15 Sept

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 sign for The Little Lion Inn with a lion emblem, indicating a themed establishment.

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

9. The Little Lion

Great Barrington

Anne

€108

includes taxes & fees

15 Sept - 16 Sept

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.

10. Prospect Berkshires

Egremont

Kellee

€343

includes taxes & fees

17 Sept - 18 Sept

A group of people performing yoga in an outdoor setting with grass and trees.

A hotel room with a bed, two chairs, a small table, and a lamp.

A hotel room with a flat-screen TV, a microwave, a refrigerator, a wooden dresser, a bedside lamp, and a framed picture on the wall.

A motel with a row of rooms, a parking lot, and a red car parked in front.

11. Pleasant Valley Motel West Stockbridge

West Stockbridge

Peter

€65

includes taxes & fees

26 Aug - 27 Aug

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.

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

Jennifer

€184

includes taxes & fees

27 Aug - 28 Aug

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 backyard with a swimming pool, lounge chairs, and a hot tub.

A bar with wooden floors and shelves filled with bottles.

13. The Red Lion Inn

Stockbridge

Patricia

€193

includes taxes & fees

8 Sept - 9 Sept

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.

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

Great Barrington

Lisa

€186

includes taxes & fees

1 Sept - 2 Sept

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

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

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

15. Shaker Mill Inn

West Stockbridge

Mervin

€168

includes taxes & fees

26 Aug - 27 Aug

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

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.

16. Quality Inn Lee - Lenox South

Lee

Christine

€105

includes taxes & fees

15 Sept - 16 Sept

A wooden deck with white railings and hanging flower baskets.

A building with a balcony covered in pink flowers, a paved driveway, and a car parked in the background.

A two-story building with a balcony, a red door, and a staircase leading to the second floor.

A hotel room with two queen beds, a desk, a chair, a lamp, and a window with curtains.

17. Chatham Travel Lodge

Old Chatham

Shruti

€107

includes taxes & fees

27 Aug - 28 Aug

18. Berkshire Travel Lodge

Austerlitz

Kris

€65

includes taxes & fees

3 Sept - 4 Sept

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

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.

A traditional living room with a fireplace, floral patterned sofa, and a patterned rug.

19. Changing Times Boutique Country Lodging

Craryville

Thomas

€192

includes taxes & fees

31 Aug - 1 Sept

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

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

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

Lee

Rinat

€122

includes taxes & fees

15 Sept - 16 Sept

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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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Mosquito Island

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

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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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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

"Clean room. Nice hotel. Great option in the Lenox area."

Best Western Plus Berkshire Hills Inn & Suites

10/10 Excellent

"Fine place to stay in the Lenox area."

Quality Inn Great Barrington

10/10 Excellent

"If you're looking for a nice basic hotel with breakfast and free parking, I highly recommend this Quality Inn in Great Barrington, MA. Our room was clean, comfortable, and well priced. Breakfast included a nice variety of hot and cold food items. The scrambled eggs and sausage links were very tasty, and so were the make-your-own waffles. The staff were very nice. I look forward to returning. Note: A freight rail line runs through Great Barrington once a day."

voco James Newbury Hudson Valley by IHG

8/10 Good

"Great setting along the Hudson River. Kind of noisy . Lots of hard surfaces. Staff were very nice. Food was good. Needed a lite blanket, one on bed was heavy . Thanks for a lovely stay."

Pocketbook Hotel and Bath

10/10 Excellent

"Great spa"

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

10/10 Excellent

"We really enjoyed staying at postcard, room were clean and everything was so organized and clean. Really like we can cook our food. Only thing is it will be great if you can put small mirror in the bathroom or room."

Holiday Inn Club Vacations Oak 'n Spruce Resort

10/10 Excellent

"Oak’n’Spruce is a lovely resort in a wonderful area of the Berkshires. Very nice amenities, along with pools, tennis, mini golf, ping pong and other family activities. Best of all, it’s a short drive to the charming town of Stockbridge, a short drive to Tanglewood, and another short drive to Jacob’s pillow, a wonderful indoor and outdoor dance performance venue. We stay there often, and always makes four a cultural experience and wonderful family time."

Howard Johnson by Wyndham Saugerties

10/10 Excellent

"Very great stay and cleanest!"

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent

"I liked the balcony overlooking the lake"

More cheap stays in Hillsdale

FairBridge Inn Express

16 Cheshire Road Pittsfield MA

€59

15 Sept - 16 Sept

includes taxes & fees

Howard Johnson by Wyndham Lenox

462 Pittsfield Rd Lenox MA

€76

9 Sept - 10 Sept

includes taxes & fees

7.6/10 Good! (903 reviews)

Quality Inn Great Barrington

372 Main Street Great Barrington MA

€89

23 Sept - 24 Sept

includes taxes & fees

8.6/10 Excellent! (1,025 reviews)

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

1055 South Street Pittsfield MA

€114

24 Sept - 25 Sept

includes taxes & fees

The Yankee Inn

461 Pittsfield Rd Lenox MA

€151

22 Sept - 23 Sept

includes taxes & fees

9.2/10 Wonderful! (1,020 reviews)

Pocketbook Hotel and Bath

549 Washington Street Hudson NY

€256

31 Aug - 1 Sept

includes taxes & fees

8.6/10 Excellent! (66 reviews)

Frequently asked questions

Where is the best place to stay in Hillsdale?

Located 20.3 mi (32.7 km) from the heart of Hillsdale, The Yankee Inn is a top choice for your stay, based on our traveller data. Two other options for your trip to the area are Berkshire Mountain Lodge and FairBridge Inn Express. See all available top hotels, or vacation rentals in Hillsdale.

What are some of the best holiday rentals that Hillsdale has to offer?

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country: This holiday home rental outside of Hillsdale is located near skiing, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games. See all 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 family accommodation 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. Also, attractions in the area such as Hotchkiss Mobile Studio and Stoddard Corner are fun for children of all ages. Find more child-friendly accommodations in Hillsdale.

What's the best hotel for a romantic holiday in Hillsdale?

Farm House Getaway on beautiful horse farm! is a favourite country house for couples, and features in-room fireplaces and a garden. See all romantic hotels 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. Hudson valley and The Berkshires Cottage is another good option for you and your pet. See more pet-friendly hotel accommodations in Hillsdale.

What are some accommodation options with pools in Hillsdale?

The Yankee Inn: Features a seasonal outdoor pool, an indoor pool and buffet. Berkshire Mountain Lodge and Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG 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 58 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.

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Hudson Holiday Rentals

Hillsdale Hotels

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. Monument Mountain Motel

6. the Alander

7. Travelodge by Wyndham Great Barrington Berkshires

8. East Rock Inn

9. The Little Lion

10. Prospect Berkshires

11. Pleasant Valley Motel West Stockbridge

12. Wilder House Berkshires

13. The Red Lion Inn

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

15. Shaker Mill Inn

16. Quality Inn Lee - Lenox South

17. Chatham Travel Lodge

18. Berkshire Travel Lodge

19. Changing Times Boutique Country Lodging

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

Stay near popular Hillsdale attractions

Catamount Aerial Adventure Park

Copake Lake

Hillsdale Town Hall

Mosquito Island

Community Library

Roe Jan Brewing Co.

Learn more about Hillsdale

Top Hillsdale Hotel Reviews

Berkshire Mountain Lodge

Best Western Plus Berkshire Hills Inn & Suites

Quality Inn Great Barrington

voco James Newbury Hudson Valley by IHG

Pocketbook Hotel and Bath

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Holiday Inn Club Vacations Oak 'n Spruce Resort

Howard Johnson by Wyndham Saugerties

The Black Swan Lee - Lenox, an Ascend Collection Hotel

More cheap stays in Hillsdale

FairBridge Inn Express

Howard Johnson by Wyndham Lenox

Quality Inn Great Barrington

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

The Yankee Inn

Pocketbook Hotel and Bath

Frequently asked questions

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