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Hotels in Hillsdale

October 2026
17
November 2026

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Next weekend
Oct 23 - Oct 25
In two weeks
Oct 30 - Nov 1

Where to stay in Hillsdale?

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

The Brooks Motel
Hillsdale
$146
$163 total
includes taxes & fees
Oct 18 - Oct 19
The Brooks Motel
A rustic interior with wooden tables and chairs, brick walls, and a large wooden beam structure.
A wooden fire pit surrounded by six Adirondack chairs in a forested area.
A house with a stone patio and wooden stools.
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

Little Cat Lodge
Copake Falls
$152
$170 total
includes taxes & fees
Nov 2 - Nov 3
Little Cat Lodge
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'.

3. Quality Inn Great Barrington

Quality Inn Great Barrington
Downtown Great Barrington
$76
$85 total
includes taxes & fees
Nov 8 - Nov 9
Quality Inn Great Barrington
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 breakfast area with a counter, coffee machine, and a display of pastries.

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

Holiday Inn Express Hotel & Suites Great Barrington by IHG
Great Barrington
$83
$93 total
includes taxes & fees
Nov 17 - Nov 18
Holiday Inn Express Hotel & Suites Great Barrington by IHG
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 wall with a white pendant light fixture.
A wooden deck with a dog silhouette against a backdrop of autumn foliage.

5. Prospect Berkshires

Prospect Berkshires
Egremont
$284
$350 total
includes taxes & fees
Nov 10 - Nov 11
Prospect Berkshires
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 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.

6. the Alander

the Alander
Copake
$140
$157 total
includes taxes & fees
Oct 19 - Oct 20
the Alander
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.

7. Monument Mountain Motel

Monument Mountain Motel
Great Barrington
$67
$74 total
includes taxes & fees
Nov 1 - Nov 2
Monument Mountain Motel
A Fairfield by Marriott hotel with a covered entrance, multiple stories, and a well-maintained lawn.
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.
An indoor swimming pool with a diving board, lounge chairs, and a 'No Diving' sign.

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

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Great Barrington
$144
$160 total
includes taxes & fees
Nov 2 - Nov 3
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
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 sign for East Rock Inn with a mountainous logo, surrounded by lush greenery and a gravel path leading to a building.

9. East Rock Inn

East Rock Inn
Great Barrington
$122
$136 total
includes taxes & fees
Nov 14 - Nov 15
East Rock Inn
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 hotel room with a sofa, a wooden table, a lamp, a telephone, and a painting on the wall.
A motel with a two-story structure, multiple rooms with red doors, and a central staircase.

10. Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires
Great Barrington
$79
$88 total
includes taxes & fees
Oct 18 - Oct 19
Travelodge by Wyndham Great Barrington Berkshires
A large house with a balcony and a grassy yard.
A two-story building with a gabled roof and a chimney.
A hotel room with two beds, a nightstand with a lamp, and a framed picture on the wall.
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

The Little Lion
Great Barrington
$115
$128 total
includes taxes & fees
Oct 18 - Oct 19
The Little Lion
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 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.

12. Granville House

Granville House
Housatonic
$254
$284 total
includes taxes & fees
Oct 25 - Oct 26
Granville House
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 stone fireplace with a television above it, a kitchen area to the left, and a wooden floor.
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.

13. Shaker Mill Inn

Shaker Mill Inn
West Stockbridge
$128
$140 total
includes taxes & fees
Nov 1 - Nov 2
Shaker Mill Inn
A reception area with a fireplace, seating, and a doormat with the logo "Quality".
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

Quality Inn Lee - Lenox South
Lee
$93
$103 total
includes taxes & fees
Nov 8 - Nov 9
Quality Inn Lee - Lenox South
A hotel room with a bed, a desk, and two wall-mounted lamps.
A small kitchenette with a coffee maker, toaster, and cabinets. There is a red and green patterned floor and a plant on the left.
A motel with a parking lot, a signboard, and a lawn with plants.
A hotel reception desk with an orange counter, a computer, a beverage cooler, and framed awards on the wall.

15. Econo Lodge Lee - Great Barrington

Econo Lodge Lee - Great Barrington
Lee
$65
$73 total
includes taxes & fees
Nov 6 - Nov 7
Econo Lodge Lee - Great Barrington
A modern bathroom with a freestanding bathtub, a fireplace, and two framed posters 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.
A swimming pool with a surrounding deck, a stone wall, and a building in the background.

16. The Yankee Inn

The Yankee Inn
Lenox
$106
$118 total
includes taxes & fees
Nov 1 - Nov 2
The Yankee Inn
Outdoor pool
Lobby sitting area
Front of property
Lobby sitting area

17. Berkshire Travel Lodge

Berkshire Travel Lodge
Austerlitz
$75
$84 total
includes taxes & fees
Oct 21 - Oct 22
Berkshire Travel Lodge
A wooden deck with a lattice railing, surrounded by lush greenery and a gravel path.
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.
A wooden deck with a staircase leading to a porch, a white door, and hanging flower baskets.

18. Micosta Leisure Inn

Micosta Leisure Inn
Hudson
$113
$127 total
includes taxes & fees
Oct 20 - Oct 21
Micosta Leisure Inn
A group of people performing yoga in an outdoor setting with grass and trees.
A reception desk with a framed floral painting, a deer head, and a sign about pets.
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 hilly backdrop.

19. Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge
West Stockbridge
$77
$84 total
includes taxes & fees
Oct 18 - Oct 19
Pleasant Valley Motel West Stockbridge
Interior detail
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.

20. Wilder House Berkshires

Wilder House Berkshires
Sheffield
$193
$215 total
includes taxes & fees
Oct 29 - Oct 30
Wilder House Berkshires
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Go beyond your typical stay in Hillsdale

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Pet friendly
Pet friendly
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Pool
Pool
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Hot tub
Hot tub
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Spa
Spa
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Family friendly
Family friendly
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Apart hotel
Apart hotel
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Apart­ment
Apart­ment
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Cottage
Cottage
Our prices for hotels in Hillsdale are cheapest in April

Price trends for hotels in Hillsdale

Pricing is based on two traveler single night rates
View properties in October

October

High 16°C / low 7°C. Sunny most days.
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Monthly weather averages (˚C)

Top landmarks in Hillsdale

Catamount Aerial Adventure Park

6.4/10 (5 reviews)
Catamount Aerial Adventure Park is 2.2 mi (3.5 km) from central Hillsdale, why not stop by during your stay.
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Copake Lake

Copake Lake is 0.7 mi (1.2 km) from central Copake Lake, why not stop by during your stay.
See properties

Hillsdale Town Hall

Hillsdale Town Hall is worth a visit when in central Hillsdale.
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Community Library

Community Library is worth a visit, located 0.9 mi (1.4 km) from central Hillsdale.
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Roe Jan Brewing Co.

You could stop off for a few afternoon drinks at Roe Jan Brewing Co. when visiting Hillsdale.
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Mosquito Island

Mosquito Island is 1.2 mi (1.9 km) from central Copake Lake, why not stop by during your stay.
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Learn more about Hillsdale

Hillsdale is well-known for its attractions such as Catamount Aerial Adventure Park and Catamount Ski Area. The city has something for everyone including sights like Copake Lake and Hillsdale Town Hall within a small-town setting.

See all hotels in Hillsdale
A landscape with a row of trees in autumn colors, a wooden fence, and a hilly background.

Check out reviews of Hillsdale hotels guests love

A rustic interior with wooden tables and chairs, brick walls, and a large wooden beam structure.
A wooden fire pit surrounded by six Adirondack chairs in a forested area.
A house with a stone patio and wooden stools.
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.

Little Cat Lodge

Little Cat Lodge
Copake Falls

10/10 Exceptional

United States
Elisabeth
Little Cat Lodge
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'.

Quality Inn Great Barrington

Quality Inn Great Barrington
Downtown Great Barrington

10/10 Exceptional

United States
Andrew
Quality Inn Great Barrington
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 wall with a white pendant light fixture.
A wooden deck with a dog silhouette against a backdrop of autumn foliage.

Prospect Berkshires

Prospect Berkshires
Egremont

10/10 Exceptional

United States
Emily
Prospect Berkshires
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 sign for East Rock Inn with a mountainous logo, surrounded by lush greenery and a gravel path leading to a building.

East Rock Inn

East Rock Inn
Great Barrington

10/10 Exceptional

United States
Heather
East Rock Inn
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.

Monument Mountain Motel

Monument Mountain Motel
Great Barrington

10/10 Exceptional

United States
Anthony
Monument Mountain Motel
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 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.

the Alander

the Alander
Copake

10/10 Exceptional

United States
Steve
the Alander
A Fairfield by Marriott hotel with a covered entrance, multiple stories, and a well-maintained lawn.
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.
An indoor swimming pool with a diving board, lounge chairs, and a 'No Diving' sign.

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

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

10/10 Exceptional

United States
Anonymous traveler
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
A wooden deck with a lattice railing, surrounded by lush greenery and a gravel path.
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.
A wooden deck with a staircase leading to a porch, a white door, and hanging flower baskets.

Micosta Leisure Inn

Micosta Leisure Inn
Hudson

10/10 Exceptional

United States
marisa
Micosta Leisure Inn
Interior detail
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.

Wilder House Berkshires

Wilder House Berkshires
Sheffield

10/10 Exceptional

United States
joseph
Wilder House Berkshires
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.

Changing Times Boutique Country Lodging

Changing Times Boutique Country Lodging
Craryville

10/10 Exceptional

United States
Kathleen
Changing Times Boutique Country Lodging
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 stone fireplace with a television above it, a kitchen area to the left, and a wooden floor.
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.

Shaker Mill Inn

Shaker Mill Inn
West Stockbridge

10/10 Exceptional

United States
Joe
Shaker Mill Inn
A large house with a balcony and a grassy yard.
A two-story building with a gabled roof and a chimney.
A hotel room with two beds, a nightstand with a lamp, and a framed picture on the wall.
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.

The Little Lion

The Little Lion
Great Barrington

10/10 Exceptional

United States
Hong
The Little Lion
An indoor swimming pool with clear water, tiled floors, and a blue wall.
A reception area with a modern design, including a reception desk, a Holiday Inn Express sign, and a refrigerator stocked with beverages.
A modern hotel with a large entrance, multiple floors, and a well-lit facade.
A modern cafe with a counter, seating area, and large windows.

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

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

10/10 Exceptional

United States
Bruce
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
A modern kitchen with a built-in oven, microwave, and stainless steel range hood.
A two-story building with a brick facade and a flat roof.
A modern interior with a round mirror reflecting a dining area, a large vase, and a guitar.
An outdoor seating area with a stone table and wicker furniture.

Howard Hotel

Howard Hotel
Hudson

10/10 Exceptional

United States
Gianina
Howard Hotel
A kitchen with a stainless steel sink, a window with a view of a wooden deck and yellow chairs, and a door leading to an outdoor area.
A black rocking chair in front of a house with a sign that reads "The Nest" and a small potted plant beside the door.
A bedroom with a large bed, a desk with a mirror, a television on the wall, and a chandelier.
A hallway with a bed in the background, a door with the number 4, and a small table with water bottles and a coffee maker.

The Nest Hudson

The Nest Hudson
Hudson

10/10 Exceptional

United States
Thom
The Nest Hudson
An aerial view of a large estate with multiple buildings, surrounded by dense greenery and trees.
A wooden interior with a table, chair, and a view of a red barn through an open door.
A spacious living room with a high ceiling, wooden beams, a fireplace, and a bookshelf filled with books.
A spacious living room with high ceilings, exposed wooden beams, a fireplace, and comfortable seating.

Inn at Silver Maple Farm

Inn at Silver Maple Farm
East Chatham

10/10 Exceptional

United States
Michelle
Inn at Silver Maple Farm
A modern bathroom with a freestanding bathtub, a fireplace, and two framed posters 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.
A swimming pool with a surrounding deck, a stone wall, and a building in the background.

The Yankee Inn

The Yankee Inn
Lenox

10/10 Exceptional

United States
Colleen
The Yankee Inn

Frequently Asked Questions

What accommodations do travelers recommend in Hillsdale?

Guests like Quality Inn Great Barrington.

Can I book a refundable accommodation in Hillsdale?

If you want the flexibility to change your travel plans to Hillsdale, most hotels offer refundable* rates you can book. You can find these accommodations by searching our site and using the "fully refundable" filter to narrow the results down.

Where can I stay in Hillsdale if I want a vacation home instead of a traditional hotel?

If you want to find a good alternative to a hotel, review our selection of 46 vacation homes.

What will the weather in Hillsdale be like during my vacation?

The warmest months in Hillsdale are usually July and August with an average temp of 68°F. January and February are the chilliest months when the average temp is 29°F. The rainiest months are October and August.

Why should I book my Hillsdale accommodation with Hotels.com?

There are plenty of reasons to book your Hillsdale travel with us: our free cancellations on selected hotels* gives you the flexibility you're looking for, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™** on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.