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Hotels in Canaan

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Where to stay in Canaan?

An aerial view of a large estate with multiple buildings, surrounded by dense greenery and trees.

A spacious kitchen with wooden beams, a dining area with a large table and chairs, and a view of the outdoors through large windows.

A wooden interior with a table, chair, and a view of a red barn through an open door.

A spacious living room with high ceilings, exposed wooden beams, a fireplace, and comfortable seating.

1. Inn at Silver Maple Farm

East Chatham

$194

$217 total

includes taxes & fees

Nov 4 - Nov 5

A hotel room with a large bed, a flat-screen TV, a fireplace, a desk with a chair, and a nightstand with lamps.

A Best Western Plus hotel with a two-story building, a covered front entrance, and a parking lot.

A hotel room with a patterned carpet, a sofa, a chair, a small table, a lamp, a television on a cabinet, and two framed pictures on the wall.

A reception area with a coffee machine, a water dispenser, and a sign indicating the fitness center.

2. Best Western Plus Berkshire Hills Inn & Suites

Pittsfield

$93

$104 total

includes taxes & fees

Nov 1 - Nov 2

3. Berkshire Travel Lodge

Austerlitz

$75

$84 total

includes taxes & fees

Oct 8 - Oct 9

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 cozy room with a wooden desk, a chair with a blanket, a fireplace with a fire, a mirror, and a poster on the wall.

4. The Yankee Inn

Lenox

$106

$118 total

includes taxes & fees

Nov 1 - Nov 2

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 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.

5. Shaker Mill Inn

West Stockbridge

$137

$150 total

includes taxes & fees

Nov 1 - Nov 2

A hotel room with a large bed, bedside lamps, a desk with a computer, a microwave, and framed pictures on the wall.

A hotel room with a dining area, a sofa, a coffee station, and a TV mounted on the wall.

A multi-story motel with a central courtyard, individual rooms with balconies, and a parking lot.

A hotel room with a dining area featuring a table and chairs, a kitchenette with a coffee machine, and a television on the wall.

6. Howard Johnson by Wyndham Lenox

Lenox

$79

$88 total

includes taxes & fees

Oct 8 - Oct 9

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

An indoor swimming pool with clear glass walls, a hot tub area, and a seating area with chairs and tables.

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.

7. Courtyard by Marriott Lenox Berkshires

Lenox

$126

$140 total

includes taxes & fees

Nov 1 - Nov 2

A wooden deck with white railings and hanging flower baskets.

A bathroom with a bathtub, toilet, and sink. There is a shower curtain, a towel rack, and a hairdryer.

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

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

8. Chatham Travel Lodge

Old Chatham

$112

$125 total

includes taxes & fees

Oct 8 - Oct 9

A spacious hotel lobby with multiple seating areas, large windows, and a television.

A hotel with a brick facade, a covered entrance, and an American flag.

A large indoor swimming pool with clear water, surrounded by tiled walls and a tiled floor.

9. Hampton Inn & Suites Berkshires-Lenox

Lenox

$115

$128 total

includes taxes & fees

Nov 5 - Nov 6

A spacious lobby with a fireplace, multiple seating areas, and a chandelier.

A garden with wooden Adirondack chairs and a stone pathway.

An indoor swimming pool with a high ceiling, multiple windows, and seating areas.

A spacious lobby with a fireplace, seating area, and a bar.

10. Berkshire Mountain Lodge

Pittsfield

$96

$129 total

includes taxes & fees

Oct 18 - Oct 19

An indoor swimming pool with clear water, tiled floors, and a blue wall.

A modern hotel with a large entrance, multiple floors, and a well-lit facade.

A reception area with a modern design, including a reception desk, a Holiday Inn Express sign, and a refrigerator stocked with beverages.

A modern cafe with a counter, seating area, and large windows.

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

Pittsfield

$103

$115 total

includes taxes & fees

Nov 5 - Nov 6

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 motel with a row of rooms, a parking lot, and a hilly backdrop.

A reception desk with a framed floral painting, a deer head, and a sign about pets.

12. Pleasant Valley Motel West Stockbridge

West Stockbridge

$77

$84 total

includes taxes & fees

Oct 8 - Oct 9

A modern kitchen with a central island, bar seating, and a dining area with chairs and a table.

A hotel with a covered entrance, multiple floors, and a landscaped area with flowers and shrubs.

A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a dining area with a wooden table and chairs.

An outdoor seating area with Adirondack chairs and a fire feature.

13. Element by Marriott Lenox Berkshires

Lenox

$135

$151 total

includes taxes & fees

Nov 5 - Nov 6

A restaurant with a large Buddha statue in the center, multiple dining tables with chairs, and a carpeted floor.

A large indoor swimming pool with multiple lanes, surrounded by lounge chairs and a glass wall.

A spacious living room with a large sofa, a coffee table, and a fireplace.

A bar area with a central island, red bar stools, and shelves stocked with bottles and glasses.

14. Hilton Garden Inn Lenox Pittsfield

Pittsfield

$128

$143 total

includes taxes & fees

Nov 1 - Nov 2

A building entrance with a large planter with purple flowers and a small tree.

A library with bookshelves, a television, and two armchairs.

A restaurant with a large open dining area, wooden tables and chairs, and a brick wall with a colorful mural.

A lobby with a red sofa, two armchairs, a wooden table with a vase, brick walls, and an ornate ceiling.

15. Hotel On North

Pittsfield

$114

$127 total

includes taxes & fees

Nov 4 - Nov 5

A spacious hotel lobby with high ceilings, large windows, and a central seating area with a chandelier.

An outdoor seating area with a sofa, chairs, and tables, and a building with large windows and a door labeled "Hotel Entrance".

A cozy library with bookshelves, a sofa, a coffee table, and a large window with a view of trees.

A spacious bar area with a long counter and multiple stools, a seating area with a sofa and chairs, and a view through large windows to the outdoors.

16. Berkshires Untold

Lenox

$136

$152 total

includes taxes & fees

Nov 1 - Nov 2

A hotel room with a large bed, two bedside lamps, a chair, and a window with curtains.

A fenced outdoor area with a pool, lounge chairs, and umbrellas.

A swimming pool with lounge chairs and umbrellas, surrounded by trees and buildings.

A residential street with a paved road, a lamp post, and flowering trees.

17. Berkshire Inn

Pittsfield

$86

$96 total

includes taxes & fees

Oct 12 - Oct 13

A modern living room with a fireplace, two blue armchairs, and decorative vases on the mantel.

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.

18. Quality Inn Lee - Lenox South

Lee

$93

$103 total

includes taxes & fees

Nov 1 - Nov 2

A snow-covered outdoor area with a patio, seating, and a covered dining area.

A two-story house with a balcony, a brick chimney, and a porch with Adirondack chairs.

A snow-covered outdoor area with a small bridge over a stream, surrounded by trees and illuminated by string lights.

A modern living room with a fireplace, comfortable seating, and a large window with curtains.

19. The Cornell Inn, Lenox & The Berkshires

Lenox

$156

$179 total

includes taxes & fees

Oct 27 - Oct 28

A large white house with a prominent tower, surrounded by lush greenery and a well-maintained lawn.

A sign for 'Hide Away Inn' with 'Hotel Entrance' below it, set against a snowy landscape with bare trees.

A room with a foosball table, a ping pong table, a bar area with stools, a fireplace, and a bookshelf.

A cozy room with a round table, a sofa, a leopard-print armchair, and a large window with a view.

20. Hideaway Inn Lenox

Lenox

$132

$147 total

includes taxes & fees

Nov 5 - Nov 6

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Go beyond your typical stay in Canaan

Pet friendly

Spa

Pool

Hot tub

Family friendly

Cottage

Top landmarks in Canaan

Queechy Lake

Queechy Lake is 1.7 mi (2.7 km) from central Canaan, why not stop by during your stay.

See properties

Learn more about Canaan

Canaan is well-known for its attractions such as Queechy Lake and Hollow FIelds Reserve.

See all hotels in Canaan

A calm lake with reflections of the sky and trees, surrounded by lush greenery and hills.

Check out reviews of Canaan hotels guests love

Berkshire Mountain Lodge

10/10 Excellent

"Very spacious and inviting..Loved the coffee maker in lobby!!!! All the girls at the front desk were extremely nice and welcoming. Very clean property and great location.. to Great Barrington, Lenox, Stockbridge, and Lee with great restaurants near by in those towns as well"

Vacation Village in the Berkshires

10/10 Excellent

"Very spacious and clean room , at an affordable price vast of amenities surrounded by nature"

Quality Inn Lee - Lenox South

8/10 Good

"Wonderful location. Nearby Norman Rockwell museum. Perfect for a stopover."

The Red Lion Inn

8/10 Good

"Would go there again but would request to be in the main Inn, they have properties all over the town center that are considered the Inn. That was disappointing. A very unique property and super cute!"

Holiday Inn Club Vacations Oak 'n Spruce Resort

10/10 Excellent

"Went here for our 24th Wedding Anniversary!! We picked the area so we could go to the Norman Rockwell museum. To our surprise we were upgraded to a Villa. Thank you so much Becky for the accommodations. We will be back!"

The Cornell Inn, Lenox & The Berkshires

10/10 Excellent

"Delightful and charming! When you go to an inn that is over 200 years old you don’t know what to expect and everything was a wonderful surprise. Super clean, stylish, and staff that was warm and friendly. We had what we believe was the smallest room in the Inn, not much over 100 ft.², and it was perfect for a one night stay. The breakfast options were a real treat!"

Pocketbook Hotel and Bath

8/10 Good

"."

Hotel On North

10/10 Excellent

"Beautiful boutique hotel. We will be back!"

Jiminy Peak Mountain Resort

10/10 Excellent

"Beautiful location plenty of activities and very convenient having the country store on site! Also the onsite restaurant was amazing!"

Frequently asked questions

What accommodations do travelers like in Canaan?

Guests like Berkshire Mountain Lodge, The Yankee Inn and Berkshires Untold.

Can I book refundable hotels in Canaan?

If you need the flexibility to change your plans to Canaan, most hotels offer refundable* bookable rates. You can see these accommodations by searching our site and using the "fully refundable" filter to narrow the results down.

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

Browse 7 vacation homes on our site.

What will the weather in Canaan be like during my visit?

July and August are typically the warmest months in Canaan when the average temp is 66°F. January and February are the coldest months when the average temperature is 27°F. October and August are the months with the most rain.

Why should I book my Canaan hotel through Hotels.com?

There are lots of reasons to book your Canaan trip with us: our free cancellations on selected hotels gives you flexibility, 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.

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