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Vacation Homes in Cheshire

Outdoor dining
Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!
Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!
10.0 out of 10, Exceptional, (3)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is AED 536
AED 1,386 total
includes taxes & fees
28 Oct - 29 Oct
Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!
Fridge, microwave, oven, stovetop
Foliage Galore! 14mi to Mt. Snow, Arcade, King Bed
Foliage Galore! 14mi to Mt. Snow, Arcade, King Bed
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 731
AED 1,847 total
includes taxes & fees
26 Oct - 27 Oct
Foliage Galore! 14mi to Mt. Snow, Arcade, King Bed
Terrace/patio
Charming 2-bedroom house in beautiful countryside of Cummington, Ma
Charming 2-bedroom house in beautiful countryside of Cummington, Ma
2.0 star property
The price is AED 716
AED 1,044 total
includes taxes & fees
26 Oct - 27 Oct
Charming 2-bedroom house in beautiful countryside of Cummington, Ma
Exterior
North Getaway Cottage
North Getaway Cottage
9.2 out of 10, Wonderful, (22)
"Claudia is such a considerate and thoughtful host! We felt so welcome and at ease."
United States
Caroline J.
The price is AED 744
AED 1,614 total
includes taxes & fees
27 Oct - 28 Oct
North Getaway Cottage
Fridge, microwave, oven, stovetop
Near Tanglewood: Historic Summer Retreat
Near Tanglewood: Historic Summer Retreat
9.6 out of 10, Exceptional, (22)
"Perfect cosy home to stay at for a Berkshire vacation. Easy to get to everything."
United States
Paul S.
The price is AED 638
AED 1,546 total
includes taxes & fees
26 Oct - 27 Oct
Near Tanglewood: Historic Summer Retreat
Fridge, microwave, oven, stovetop
Sun Filled Lenox Retreat - Minutes to Tanglewood!
Sun Filled Lenox Retreat - Minutes to Tanglewood!
9.4 out of 10, Exceptional, (3)
"The house is in a great location and is very user friendly and well equipped. The only suggestion I would make is to put an air conditioner in the third bedroom. Overall, a lovely stay."
United States
Sarah D.
The price is AED 698
AED 1,719 total
includes taxes & fees
30 Oct - 31 Oct
Sun Filled Lenox Retreat - Minutes to Tanglewood!
A heated pool
Comfortable Berkshires retreat on mtn resort, SISO
Comfortable Berkshires retreat on mtn resort, SISO
8.8 out of 10, Excellent, (6)
"Kind and responsive host."
United States
Javier
The price is AED 591
AED 1,792 total
includes taxes & fees
26 Oct - 27 Oct
Comfortable Berkshires retreat on mtn resort, SISO
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
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 1,806 total
includes taxes & fees
26 Oct - 27 Oct
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Exterior
Bungalow in the Berkshires
Bungalow in the Berkshires
10.0 out of 10, Exceptional, (3)
"We had a lovely stay. Easy check in and communication was great. "
United States
Dale G.
The price is AED 1,102
AED 1,534 total
includes taxes & fees
26 Oct - 27 Oct
Bungalow in the Berkshires
Property grounds
Riverbend Berkshire East Basecamp - 3 bedrooms available
Riverbend Berkshire East Basecamp - 3 bedrooms available
The price is AED 588
AED 1,551 total
includes taxes & fees
27 Oct - 28 Oct
Riverbend Berkshire East Basecamp - 3 bedrooms available
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
9.8 out of 10, Exceptional, (72)
"We had a wonderful stay, thank you! "
United States
Gary L.
The price is AED 988
AED 2,051 total
includes taxes & fees
26 Oct - 27 Oct
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
Fireplace
Artists’ Hideaway in Old Chatham
Artists’ Hideaway in Old Chatham
The price is AED 739
AED 1,651 total
includes taxes & fees
28 Oct - 29 Oct
Artists’ Hideaway in Old Chatham
Terrace/patio
Spacious 5-bedroom house in charming Lee with WiFi
Spacious 5-bedroom house in charming Lee with WiFi
8.0 out of 10, Very Good, (1)
"House was large, clean, and comfortable. "
United States
John Z.
The price is AED 1,570
AED 2,944 total
includes taxes & fees
31 Oct - 1 Nov
Spacious 5-bedroom house in charming Lee with WiFi
Exterior
Spacious 6BR Near Jiminy Peak – Hot Tub, Game Room & Ski Lift Ticket Discount
Spacious 6BR Near Jiminy Peak – Hot Tub, Game Room & Ski Lift Ticket Discount
10.0 out of 10, Exceptional, (15)
"Amazing Inn. Cozy and everything we needed. "
United States
Price F.
The price is AED 2,200
AED 4,081 total
includes taxes & fees
28 Oct - 29 Oct
Spacious 6BR Near Jiminy Peak – Hot Tub, Game Room & Ski Lift Ticket Discount
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

Berkshire Mountain Lodge

Berkshire Mountain Lodge

10/10 Excellent
"We loved this place. Quiet, very clean,attractive. Loved that it had a kitchen area. Second story, sliding glass doors overlooked the fall foliage in the back of the building. Very peaceful.."
Steven 4-night trip
Posted 2 days ago
Berkshire Mountain Lodge