Top Chalets in Canaan in 2026

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

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Recommended hotels in Canaan

1. Secluded Cabin in the Woods, where the Berkshires meet the Hudson Valley.

Canaan

includes taxes & fees

8 Sept - 9 Sept

2. Inn at Silver Maple Farm

East Chatham

Erdem

includes taxes & fees

9 Sept - 10 Sept

3. Best Western Plus Berkshire Hills Inn & Suites

Pittsfield

Prasanna

includes taxes & fees

7 Sept - 8 Sept

4. The Yankee Inn

Lenox

Karen

includes taxes & fees

28 Sept - 29 Sept

5. Berkshire Travel Lodge

Austerlitz

Kris

includes taxes & fees

15 Sept - 16 Sept

6. Chatham Travel Lodge

Old Chatham

Andrew

includes taxes & fees

8 Sept - 9 Sept

7. Shaker Mill Inn

West Stockbridge

Mervin

includes taxes & fees

9 Sept - 10 Sept

8. Howard Johnson by Wyndham Lenox

Lenox

irene

includes taxes & fees

3 Sept - 4 Sept

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Top Canaan Hotel Reviews

Holiday Inn Club Vacations Oak 'n Spruce Resort

10/10 Excellent

"Perfect stay"

Berkshire Mountain Lodge

10/10 Excellent

"Enjoyed my stay! Spacious rooms, clean, quiet, surrounded by nature, free custom coffee ☕️ in lobby, free laundry facilities (bring your own detergent), no restaurant on-site. Pittsfield had lots of dining options nearby. I recommend the local nature trails at the Audubon Sanctuary, so beautiful 😍"

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."

Find out more about Canaan

Canaan Chalets information

Number of reviews	10,373
Accommodation	6 Chalets
Lowest Price	£48
Highest Price	£132

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