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Check prices for these dates

Next weekend
31 Jan - 2 Feb
In two weeks
7 Feb - 9 Feb
In one month
21 Feb - 23 Feb
In two months
21 Mar - 23 Mar

Compare 6 Chalets in Canaan with updated reviews, rates, and availability.

Berkshires Hilltop Retreat w Magic View! 15 mins to Ski Butternut.
Main level open space (old setup)

Berkshires Hilltop Retreat w Magic View! 15 mins to Ski Butternut.

9.8 out of 10, Exceptional, (23)
"Short couples getaway to recharge. The house was perfect and the wood stove kept the house toasty through the cold windy stay. HINT: coming from NY/NJ, buy your groceries as you pass through Great Barrington and save that extra trip."
Berkshires Hilltop Retreat w Magic View! 15 mins to Ski Butternut.
Little Longbow Lakefront Chalet
Aerial view

Little Longbow Lakefront Chalet

10.0 out of 10, Exceptional, (9)
"The location was great. Very peaceful. Not far from Lee, Lenox or Great Barrington. The house was very cute and as described. Will absolutely stay again. "
Little Longbow Lakefront Chalet
Lakefront w/Dock! Family Friendly Amenities, Close to skiing and Hudson, NY
Terrace/patio

Lakefront w/Dock! Family Friendly Amenities, Close to skiing and Hudson, NY

8.8 out of 10, Excellent, (6)
"We very much enjoyed our time spent at Eagles Nest playing pickleball, ping pong, time at the pool and using the various boating equipment. Just beware as you may encounter a water snake or 2 but they are timid and we continued enjoying the dock activities such as fishing, kayaking, paddleboating or just laying on the floating mat. The kitchen and laundry room were extremely well appointed as was each bedroom with it's own tv. The lake is also an extremely quiet body of water. The one slight...
Lakefront w/Dock! Family Friendly Amenities, Close to skiing and Hudson, NY
Berkshire Chalet: Walk to Lenox. Mobility friendly, Amazing Views.Dog Friendly!
garden view of the back of the cabin, with the deck

Berkshire Chalet: Walk to Lenox. Mobility friendly, Amazing Views.Dog Friendly!

8.8 out of 10, Excellent, (3)
"We really enjoyed our stay at this adorable A frame home. The home was a quick drive to tanglewood and the views were beautiful. The owner was very communicative and prompt with answering any questions. "
Berkshire Chalet: Walk to Lenox. Mobility friendly, Amazing Views.Dog Friendly!
SRC-Hudson Valley/Berkshires Cultural Corridor
Property grounds

SRC-Hudson Valley/Berkshires Cultural Corridor

SRC-Hudson Valley/Berkshires Cultural Corridor
Majestic Lake Front Chalet
Interior

Majestic Lake Front Chalet

2.0 star property
Majestic Lake Front Chalet
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Canaan

Vacation Village in the Berkshires
Lobby

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1757)
"It had a great pool and hot tub. also right near the ski area, jiminey Peak."
The price is AED 689
AED 792 total
includes taxes & fees
26 Jan - 27 Jan
Vacation Village in the Berkshires
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
Welcome to The Freeman Berkshires

The Freeman - Newly Renovated 14K SF Estate on 40 Acres

10.0 out of 10, Exceptional, (33)
"We had a wonderful stay for our mother’s birthday with her 4 children and 10 of her 12 grandchildren. There was plenty to do for everyone especially with a 75 year difference in ages!!"
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (235)
"Very lovely place to stay. Everything was clean and the owner made everything simple."
The price is AED 551
AED 833 total
includes taxes & fees
26 Jan - 27 Jan
Berkshire Village Carriage House - Super Private!!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.