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Hotels in Canaan

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Top 5 hotels in Canaan at a glance

Inn at Silver Maple Farm — 3-star hotel in East Chatham. Guest rating: 9.8/10 — Exceptional.
Best Western Plus Berkshire Hills Inn & Suites — 2.5-star hotel in Pittsfield. Guest rating: 8.4/10 — Very Good.
The Yankee Inn — 2.5-star hotel in Lenox. Guest rating: 9.2/10 — Wonderful.
Berkshire Travel Lodge — 2.5-star hotel in Austerlitz. Guest rating: 5.4/10.
Berkshire Mountain Lodge — 3-star hotel in Pittsfield. Guest rating: 9.0/10 — Wonderful.

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 spacious living room with a high ceiling, wooden beams, a fireplace, and a bookshelf filled with books.

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

Inn at Silver Maple Farm

East Chatham

$139

$156 total

includes taxes & fees

Sep 1 - Sep 2

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

A reception area with grey upholstered chairs, a wooden reception desk, and a colorful pear painting on the wall.

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.

Best Western Plus Berkshire Hills Inn & Suites

Pittsfield

$115

$128 total

includes taxes & fees

Sep 20 - Sep 21

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 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.

The Yankee Inn

Lenox

$101

$113 total

includes taxes & fees

Sep 7 - Sep 8

Berkshire Travel Lodge

Austerlitz

$75

$84 total

includes taxes & fees

Sep 1 - Sep 2

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

A hotel lobby with a snow-covered entrance and a sign reading "Lobby".

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

A garden with wooden Adirondack chairs and a stone pathway.

Berkshire Mountain Lodge

Pittsfield

$88

$120 total

includes taxes & fees

Oct 1 - Oct 2

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 seating areas, a coffee station, and large windows offering a view of greenery.

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

Pittsfield

$118

$132 total

includes taxes & fees

Sep 8 - Sep 9

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

Shaker Mill Inn

West Stockbridge

$168

$184 total

includes taxes & fees

Sep 8 - Sep 9

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 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.

Chatham Travel Lodge

Old Chatham

$112

$125 total

includes taxes & fees

Sep 8 - Sep 9

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 featuring a table and chairs, a kitchenette with a coffee machine, and a television on the wall.

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

A gazebo with a metal roof and wooden benches, surrounded by a white fence and lush greenery.

Howard Johnson by Wyndham Lenox

Lenox

$79

$88 total

includes taxes & fees

Sep 1 - Sep 2

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

A grocery store with shelves stocked with snacks and beverages, a refrigerated display case, and a wall with hexagonal patterns.

Hampton Inn & Suites Berkshires-Lenox

Lenox

$123

$138 total

includes taxes & fees

Sep 13 - Sep 14

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 bed, two chairs, a small table, and a lamp.

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

Pleasant Valley Motel West Stockbridge

West Stockbridge

$80

$88 total

includes taxes & fees

Sep 1 - Sep 2

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

A cozy library with bookshelves, a fireplace, and comfortable seating.

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

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

Berkshires Untold

Lenox

$145

$162 total

includes taxes & fees

Sep 28 - Sep 29

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

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

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

A hotel patio with outdoor seating and a fire pit.

Hilton Garden Inn Lenox Pittsfield

Pittsfield

$148

$165 total

includes taxes & fees

Sep 13 - Sep 14

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

A hotel room with a bed, a desk, a television, a microwave, and a sofa.

A hotel room with a sofa, armchair, desk with lamp, television, mini-fridge, and patterned carpet.

Quality Inn Lee - Lenox South

Lee

$110

$122 total

includes taxes & fees

Sep 20 - Sep 21

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 lodge with a large building and a dock by a lake, surrounded by forest.

The Black Swan Lee - Lenox, an Ascend Collection Hotel

Lee

$128

$142 total

includes taxes & fees

Sep 21 - Sep 22

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

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

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

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

Berkshire Inn

Pittsfield

$86

$96 total

includes taxes & fees

Sep 1 - Sep 2

A modern hotel room with a sofa, a TV, a kitchen area with bar stools, and a patterned floor.

A multi-story hotel with a brick facade and a flat roof.

A pool area with a glass ceiling, multiple levels, and outdoor seating.

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Pittsfield

$118

$132 total

includes taxes & fees

Sep 7 - Sep 8

A hotel room with two beds, a desk, a TV, and a window with curtains.

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

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

An indoor swimming pool with a 6 feet 18 meters depth, surrounded by chairs and tables, with large windows offering views of trees.

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Great Barrington

$115

$128 total

includes taxes & fees

Sep 7 - Sep 8

A building with a registration sign above the entrance, a white porch railing, and flower baskets on the railing.

A modern apartment with a living room, kitchenette, and dining area.

A covered porch with a wooden floor and white railing, overlooking a green lawn and a clear blue sky.

A hotel room with two beds, a nightstand with a lamp, and a window with curtains.

The Central Downtown Inn & Suites

Pittsfield

$99

$111 total

includes taxes & fees

Sep 1 - Sep 2

A large, multi-story building with a swimming pool, surrounded by dense greenery and trees.

A covered porch with wicker furniture and hanging flower baskets.

A brick pathway lined with autumn foliage and pumpkins, leading to a white building with a porch decorated with hanging flowers.

A bar with wooden floors and shelves filled with bottles.

The Red Lion Inn

Stockbridge

$161

$230 total

includes taxes & fees

Sep 29 - Sep 30

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Go beyond your typical stay in Canaan

Pet friendly

Pool

Spa

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

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent

"We had a fantastic stay at the Black Swan Inn in Lee, MA. Our room was incredibly clean, comfortable, and featured a beautiful view of the lake. Both check-in and check-out were completely hassle-free .A special shoutout goes to Carrie, the breakfast attendant! The breakfast area was exceptionally clean and well-stocked thanks to her hard work. Carrie was not only helpful, pleasant, and polite, but she also worked tirelessly to ensure all food items were fresh and fully available. Her excellent service truly made our mornings. We highly recommend this inn!"

Pocketbook Hotel and Bath

8/10 Good

"Gorgeous stay - need to work out some kinks. Had to ask for a steamer 3 times to never get one. 3 times for extra pillows. The valet parking situation is a bit off. Hotel staff talking loudly with non guests how they wouldn’t spend the money to stay here. Our room had a window that was directly in the way of morning light with a window that had NO shade - brought this up and nothing was done nor apologized. The rooms are LOUD - yes the property is old and they make note but when you have old and steel tubs you need to add rugs in the room minimum. The aesthetic is beautiful and the design firm did great but if you want to charge these prices that I’m sure will climb you need to fix these small details. The restaurant was the star out our trip absolutely incredible food and lovely staff. Overall a good stay but again - some changes need to be made as you know the crowd you are attracting."

Hotel On North

10/10 Excellent

"Location is a bit in the middle of nowhere, but all else is great at this hotel. Would recommend."

Quality Inn Lee - Lenox South

8/10 Good

"Very nice and clean motel...better than I thought it would be, so we felt a lot better about staying there. We were a bit disappointed about the breakfast portion of the day so went out for brunch instead. The breakfast sandwiches weren't that great and not many tables to sit at. But overall, the rooms and bathrooms were very clean and modern."

Holiday Inn Club Vacations Oak 'n Spruce Resort

10/10 Excellent

"Great for families"

Jiminy Peak Mountain Resort

10/10 Excellent

"Nice to have a kitchenette to cook in"

Berkshire Mountain Lodge

10/10 Excellent

"Good experience"

Berkshires Untold

10/10 Excellent

"Although an excellent 2-night stay, our comments are intended to make future stays even better. Room temperature: virtually impossible to maintain a comfort level. Basically it was too cold in spite of raising the thermostat temp. At 80 when the heat came on, it was much too hot! Room lighting: too dark; only the bathroom was well lit. Bathroom moisture: in the absence of a ventilation or fan, the bathroom remained damp after a shower and keeping the door open resulted in everything in the bedroom becoming damp. But the positives far outweigh these few items."

Quality Inn Great Barrington

10/10 Excellent

"Location"

Frequently asked questions

What accommodations do travelers like in Canaan?

Guests like The Yankee Inn, Berkshire Mountain Lodge 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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