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Check prices for these dates

Next weekend
21 Saf. - 23 Saf.
In two weeks
28 Saf. - 2 Rab. I
In one month
14 Rab. I - 16 Rab. I
In two months
11 Rab. II - 13 Rab. II

Compare Chalets in Chesterfield with updated reviews, rates, and availability.

Sunny Chalet Nestled in the Woods of Ashfield
Dining

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
Little Longbow Lakefront Chalet
Aerial view

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
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 Chesterfield

Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (239)
"Property was very nice Kirchen could use some additons -starting with a ladle "
The price is SAR 563
SAR 855 total
includes taxes & fees
17 Feb - 18 Feb
Berkshire Village Carriage House - Super Private!!
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
Sandisfield Vacation Rental | 4BR | 3BA | 1,978 Sq Ft | Stairs Required

Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns

9.6 out of 10, Exceptional, (39)
"A nice cabin in the woods. Only issue was rodents at the property. We had four sighting in three days. Would stay again if they resolved the mouse problem."
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
Pristine Home In Becket Woods

Pristine Home In Becket Woods

10.0 out of 10, Exceptional, (13)
"Pristine can mean several different things. My interpretation was to be “like new”. This dwelling did not quite live up to that standard, but was clean, sans the “mud room” and what appeared to be mold on the peak of the ceiling above the living room. The original listing stated firewood was provided by the host. Then, the checkin instructions stated guests provided their own. Not huge, just misstated in the listing (since changed). There was a power outage while we were there, thus no...
Pristine Home In Becket Woods
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.