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

Hotels in Canaan

Q: What accommodations do travelers like in Canaan?

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

Where to?

Dates

November 2026

December 2026

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Where to stay in Canaan?

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

1. Inn at Silver Maple Farm

East Chatham

$184 total

includes taxes & fees

Dec 2 - Dec 3

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

2. Best Western Plus Berkshire Hills Inn & Suites

Pittsfield

$104 total

includes taxes & fees

Dec 1 - Dec 2

3. Berkshire Travel Lodge

Austerlitz

$85 total

includes taxes & fees

Nov 9 - Nov 10

Two Adirondack chairs facing a river with a forested hill in the background.

4. The Yankee Inn

Lenox

$142 total

includes taxes & fees

Nov 20 - Nov 21

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

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

Pittsfield

$111 total

includes taxes & fees

Dec 4 - Dec 5

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

6. Hampton Inn & Suites Berkshires-Lenox

Lenox

$122 total

includes taxes & fees

Nov 11 - Nov 12

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

7. Pleasant Valley Motel West Stockbridge

West Stockbridge

$78 total

includes taxes & fees

Nov 6 - Nov 7

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

8. Howard Johnson by Wyndham Lenox

Lenox

$88 total

includes taxes & fees

Nov 8 - Nov 9

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

9. Shaker Mill Inn

West Stockbridge

$159 total

includes taxes & fees

Nov 8 - Nov 9

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

10. Courtyard by Marriott Lenox Berkshires

Lenox

$140 total

includes taxes & fees

Nov 15 - Nov 16

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

11. Hotel On North

Pittsfield

$130 total

includes taxes & fees

Nov 29 - Nov 30

12. Berkshire Mountain Lodge

Pittsfield

$120 total

includes taxes & fees

Dec 6 - Dec 7

A restaurant with multiple dining tables, chairs, and a large Buddha statue centerpiece.

13. Hilton Garden Inn Lenox Pittsfield

Pittsfield

$133 total

includes taxes & fees

Nov 15 - Nov 16

A wooden deck with white railings and hanging flower baskets.

14. Chatham Travel Lodge

Old Chatham

$125 total

includes taxes & fees

Nov 8 - Nov 9

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

15. Element by Marriott Lenox Berkshires

Lenox

$151 total

includes taxes & fees

Nov 11 - Nov 12

16. Garden Gables

Lenox

$219 total

includes taxes & fees

Nov 8 - Nov 9

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

17. Berkshires Untold

Lenox

$147 total

includes taxes & fees

Dec 2 - Dec 3

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

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

Great Barrington

$101 total

includes taxes & fees

Nov 30 - Dec 1

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

19. Berkshire Inn

Pittsfield

$92 total

includes taxes & fees

Nov 28 - Nov 29

A lakeside setting with Adirondack chairs and a covered seating area, surrounded by trees and hills in the background.

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

Lee

$122 total

includes taxes & fees

Dec 3 - Dec 4

View all properties

Go beyond your typical stay in Canaan

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

Check out reviews of Canaan hotels guests love

Inn at Silver Maple Farm

East Chatham

10/10 Exceptional

Michelle

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

Pittsfield

10/10 Exceptional

William

The Yankee Inn

Lenox

10/10 Exceptional

We had a fantastic stay at the Yankee! Our adjoining rooms were clean, large and comfortable. We loved that the rooms had a fireplace and balcony! All the amenities were appreciated. The breakfast had so many offerings, including fresh fruit and two kinds of eggs. The front desk staff (especially George) were professional, helpful and friendly. This was our first stay at the Yankee, but it won't be the last!

Colleen

Shaker Mill Inn

West Stockbridge

10/10 Exceptional

This was the most comfortable B&B I have every heard of let alone stayed at. It does not have the awkwardness of eating breakfast in a community room of strangers. All the breakfast amenities are in you room, including the food that is stock daily by the inn keepers, so you get to enjoy in the comforts of your room (which is a cozy as home). The room was so spacious and well kept. Every detail is thought of by the innkeepers and if they forgot something they are accessible and gracious to...

Joe

Hotel On North

Pittsfield

10/10 Exceptional

The Hotel on North is a thoughtful and beautiful transformation of 2 old contiguous buildings, a store and factory, into a hip and fun hotel. The spaces are extremely large and open from the common spaces to the guest rooms, including the bathrooms. The aesthetic is colorful and friendly rather than the cookie cutter faux luxury I usually find in expensive hotels. The quirky design features such as vintage furniture and painted floors are a great juxtaposition to the perfect bed linens and...

Steve

Best Western Plus Berkshire Hills Inn & Suites

Pittsfield

10/10 Exceptional

Gregory

Courtyard by Marriott Lenox Berkshires

Lenox

10/10 Exceptional

Alyssa

Berkshire Mountain Lodge

Pittsfield

10/10 Exceptional

Elliott

Hilton Garden Inn Lenox Pittsfield

Pittsfield

10/10 Exceptional

Berkshires Untold

Lenox

10/10 Exceptional

High end feel at a budget friendly price. The room was boho fun but needs a few tweaks. I still give it 5 stars but wish that they had a variety of pillows on the bed, they were very nice but too thick for a stomach or back sleeper. There is a full mini bar with prices only available by QR reader, there is a free bottle of still water but since it was not marked i wasn’t sure what it was or if it was free. There is a fun wardrobe with robes but no place but the floor to put your suit case. Oh...

Jill

The Black Swan Lee - Lenox, an Ascend Collection Hotel

Lee

10/10 Exceptional

Sheila

A large, two-story house with a wrap-around porch, a covered front porch, and a small front yard.

Brook Farm Inn

Lenox

10/10 Exceptional

roberta

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

The Cornell Inn, Lenox & The Berkshires

Lenox

10/10 Exceptional

Lawrence

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Great Barrington

10/10 Exceptional

Michael

Quality Inn Lee - Lenox South

Lee

10/10 Exceptional

Anonymous traveler

A large house with a covered patio area featuring outdoor seating and a fire pit.

The Whitlock

Lenox

10/10 Exceptional

LOVED The Whitlock. Location, quality and vibe can't be beat. The outdoor gardens and patio were unexpected bonuses that are as cared for as the interior spaces. The restaurant menu was limited but the offerings were truly inspired and delicious (better than other restaurants we experienced during the trip). The bartender made a mean spicy margarita and was friendly and informed. The one low point was the complimentary continental bkfst that doesn't live up to other Whitlock experiences....

Jeff

A two-story house with a brick entrance and a white facade.

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

Stockbridge

10/10 Exceptional

Charles

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.