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Check prices for these dates

Next weekend
19 Dec - 21 Dec
In two weeks
26 Dec - 28 Dec
In one month
9 Jan - 11 Jan
In two months
6 Feb - 8 Feb

Our top choices for Cheshire vacation homes

Outdoor dining
Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!

Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!

Sherwood Forest
10.0 out of 10, Exceptional, (5)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is AED 535
AED 1,386 total
includes taxes & fees
16 Dec - 17 Dec
Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!
Fridge, microwave, oven, stovetop
Cozy Vermont Lodge |Hot Tub||Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat

Cozy Vermont Lodge |Hot Tub||Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat

Bennington
8.6 out of 10, Excellent, (34)
"The location was quite and peaceful. We enjoyed our stay and were suprised how great the wifi was for the location."
United States
Malika R.
The price is AED 367
AED 994 total
includes taxes & fees
11 Dec - 12 Dec
Cozy Vermont Lodge |Hot Tub||Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat
TV
Florida Mountain Log Cabin

Florida Mountain Log Cabin

2.0 star property
Florida
10.0 out of 10, Exceptional, (4)
"Place was super clean. Beds were comfortable. Location was great."
United States
Tristan e.
The price is AED 675
AED 1,245 total
includes taxes & fees
11 Dec - 12 Dec
Florida Mountain Log Cabin
Fridge, microwave, oven, stovetop
Foliage Galore! 14mi to Mt. Snow, Arcade, King Bed

Foliage Galore! 14mi to Mt. Snow, Arcade, King Bed

Whitingham
10.0 out of 10, Exceptional, (14)
"Extended family of 10 stayed 6 nights and all had a great stay. Beds were comfortable, house was very clean with everything you need to enjoy yourself and was in good repair. "
United States
Jacklyn D.
The price is AED 984
AED 2,168 total
includes taxes & fees
14 Dec - 15 Dec
Foliage Galore! 14mi to Mt. Snow, Arcade, King Bed
Terrace/patio
Historic Berkshires Home Near Tanglewood, Trails & Wineries

Historic Berkshires Home Near Tanglewood, Trails & Wineries

Lebanon Springs
8.8 out of 10, Excellent, (20)
"It was great - just what we were looking for. "
United States
Kaye S.
The price is AED 496
AED 1,366 total
includes taxes & fees
11 Dec - 12 Dec
Historic Berkshires Home Near Tanglewood, Trails & Wineries
Exterior
North Getaway Cottage

North Getaway Cottage

Williamstown
9.2 out of 10, Wonderful, (24)
"The cottage was the perfect accommodations for our overnight stay in town for a funeral. Thank you Claudia. "
United States
Mary Alice H.
The price is AED 859
AED 1,785 total
includes taxes & fees
12 Dec - 13 Dec
North Getaway Cottage
Fridge, microwave, oven, stovetop
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

2.0 star property
Pittsfield
7.8 out of 10, Good, (6)
"Very clean and spacious! We enjoyed our stay with our small pup!"
United States
Ann C.
The price is AED 988
AED 1,810 total
includes taxes & fees
11 Dec - 12 Dec
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Fridge, microwave, oven, stovetop
The Greylock Cabin

The Greylock Cabin

Florida
10.0 out of 10, Exceptional, (4)
"Wonderful view, peaceful quiet area, cosy cabin."
United States
Anonymous traveler
The price is AED 771
AED 1,368 total
includes taxes & fees
15 Dec - 16 Dec
The Greylock Cabin
Property grounds
Riverbend Berkshire East Basecamp - 3 bedrooms available

Riverbend Berkshire East Basecamp - 3 bedrooms available

Charlemont
The price is AED 588
AED 1,526 total
includes taxes & fees
18 Dec - 19 Dec
Riverbend Berkshire East Basecamp - 3 bedrooms available
Panoramic House | Private kitchen
Two Brooks Lodge

Two Brooks Lodge

3.0 star property
Bennington
4.8 out of 10, (3)
"Stayed at this property everything was as stated but then property manager made me pay cleaning fee and deposit through cash app , Then later Said I didn’t pay for property when I clearly did had receipts then after confronted by Expedia , He lies say I left the house a mess and that displaced half the water out of the hot tub that I didn’t use at all and didn’t do the dishes which I did , not to mentions I paid a cleaning fee either way . So this unprofessional listing gets keep the deposit...
United States
Hunter
Two Brooks Lodge
Exterior
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con

Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con

Hancock
9.8 out of 10, Exceptional, (72)
"Great communication. Lots of games for the kids. Comfortable beds. Great living and game room. "
United States
Samuel R.
The price is AED 970
AED 2,010 total
includes taxes & fees
11 Dec - 12 Dec
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
Property grounds
Walk into town, soak up sun on enclosed porch & steps away from nature trails!

Walk into town, soak up sun on enclosed porch & steps away from nature trails!

Stockbridge
10.0 out of 10, Exceptional, (29)
"Great stay in a well appointed house close to trails, Stockbridge center, and a quick car trip to Lenox, Great Barrington, Tanglewood, Jacobs Pillow, and Shakespeare & Co. we enjoyed the morning walks, coffee at the Lost Lamb, drinks at the Red Lion Inn, dance at Jacob’s Pillow, music at Tanglewood, ice cream at High Lawn Farm, and just that Berkshire vibe! "
United States
Phillip F.
The price is AED 1,686
AED 3,134 total
includes taxes & fees
11 Dec - 12 Dec
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Outdoor dining
Charlemont Chalet - A 15 Acre Private Retreat

Charlemont Chalet - A 15 Acre Private Retreat

2.0 star property
Charlemont
The price is AED 1,350
AED 2,467 total
includes taxes & fees
18 Dec - 19 Dec
Charlemont Chalet - A 15 Acre Private Retreat
Terrace/patio
Spacious 5-bedroom house in charming Lee with WiFi

Spacious 5-bedroom house in charming Lee with WiFi

Lee
8.0 out of 10, Very Good, (1)
"House was large, clean, and comfortable. "
United States
John Z.
The price is AED 1,561
AED 2,900 total
includes taxes & fees
17 Dec - 18 Dec
Spacious 5-bedroom house in charming Lee with WiFi
Exterior
Hancock Village Inn Near Jiminy Peak

Hancock Village Inn Near Jiminy Peak

Hancock
10.0 out of 10, Exceptional, (16)
"Amazing Inn. Cozy and everything we needed. "
United States
Price F.
The price is AED 2,163
AED 4,035 total
includes taxes & fees
15 Dec - 16 Dec
Hancock Village Inn Near Jiminy Peak
A heated pool
Comfortable Berkshires retreat on mtn resort, SISO

Comfortable Berkshires retreat on mtn resort, SISO

Hancock
9.0 out of 10, Wonderful, (7)
"Kind and responsive host."
United States
Javier
The price is AED 1,183
AED 2,690 total
includes taxes & fees
24 Dec - 25 Dec
Comfortable Berkshires retreat on mtn resort, SISO
Interior
Artists’ Hideaway in Old Chatham

Artists’ Hideaway in Old Chatham

Old Chatham
The price is AED 825
AED 1,892 total
includes taxes & fees
19 Dec - 20 Dec
Artists’ Hideaway in Old Chatham
Fridge, microwave, oven, stovetop
Berkshire House Stay

Berkshire House Stay

Lee
10.0 out of 10, Exceptional, (21)
"Wonderful stay, beautiful, well equipped and clean property. Highly recommend for an adult famiky getaway "
United States
jennifer r.
The price is AED 2,262
AED 4,057 total
includes taxes & fees
20 Dec - 21 Dec
Berkshire House Stay
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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Top Cheshire Hotel Reviews

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

10/10 Excellent
"Excellent stay, nice, clean 2 bedroom Villa, staff excellent, amenities excellent, great location would definitely stay again "
Tracy 2-night trip
Posted 2 days ago
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG