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Check prices for these dates

Next weekend
4 Apr - 6 Apr
In two weeks
11 Apr - 13 Apr
In one month
25 Apr - 27 Apr
In two months
23 May - 25 May

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

Little Longbow Lakefront Chalet
Smart TV, fireplace

Little Longbow Lakefront Chalet

9.2 out of 10, Wonderful, (10)
"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
Sunny Chalet Nestled in the Woods of Ashfield
Interior

Sunny Chalet Nestled in the Woods of Ashfield

9.4 out of 10, Exceptional, (15)
"Great spot for a friends' getaway! The house is spacious with a bright, big living room perfect for gatherings. The location is stunning, nestled in a beautiful area with a hiking trail right in the backyard. Plus, there are interesting places to visit nearby like Historic Deerfield and Shelburne Falls. The only downside was some machinery noise from the first floor, especially at night. Overall, a lovely stay!"
Sunny Chalet Nestled in the Woods of Ashfield
Private Luxury Chalet-Hot Tub-Heated Pool-Firepit-Game Rooms-Fits 16 people
Outdoor spa tub

Private Luxury Chalet-Hot Tub-Heated Pool-Firepit-Game Rooms-Fits 16 people

10.0 out of 10, Exceptional, (1)
"Rimon and Sallie's place is fantastic. Very clean with everything we needed for our stay. The kids were able to have their own separate space, and the common areas were great for food prep and sitting down for meals. The kids loved the hot tub and were in 3 separate times (even in the freezing temps!).The house is very private on a beautiful road, and is a short drive to Troy, Albany, etc. We had a great dinner at Hill Creek Tavern 5 minutes from the house. I would absolutely recommend this...
Private Luxury Chalet-Hot Tub-Heated Pool-Firepit-Game Rooms-Fits 16 people
SRC-Hudson Valley/Berkshires Cultural Corridor
Exterior

SRC-Hudson Valley/Berkshires Cultural Corridor

SRC-Hudson Valley/Berkshires Cultural Corridor
Secluded Mountain Chalet
Smart TV

Secluded Mountain Chalet

10.0 out of 10, Exceptional, (2)
"We had a wonderful time - delightfully snowy and the house was quiet and cozy."
Secluded Mountain 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 Cheshire

19th c. Barn in the Berkshires
Interior

19th c. Barn in the Berkshires

9.6 out of 10, Exceptional, (85)
"Amazing property, very clean- "
19th c. Barn in the Berkshires
Vacation Village in the Berkshires
Indoor pool, outdoor pool, pool umbrellas

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1792)
"Very nice accomodations, more like a mini apartment than a motel room. "
The price is AED 474
AED 560 total
includes taxes & fees
25 Mar - 26 Mar
Vacation Village in the Berkshires
Jiminy Peak Mountain Resort
Exterior

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very Good, (925)
"Staff was exceptionally helpful and friendly."
The price is AED 493
AED 540 total
includes taxes & fees
1 Apr - 2 Apr
Jiminy Peak Mountain Resort
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.