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Vacation Homes in Windsor

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!
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
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking
9.6 out of 10, Exceptional, (8)
"Very nice location with tons of privacy, yet not too far from things to do. Very easy for our dog to navigate the property as well."
United States
James D.
The price is AED 588
AED 1,441 total
includes taxes & fees
27 Oct - 28 Oct
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking
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
Couples 2 Bedroom Retreat-Close to Shelburne Falls
10.0 out of 10, Exceptional, (4)
"This place was great! Even though it was raining we enjoyed the hot tub! It was super clean and comfortable. "
United States
KayKay S.
The price is AED 624
AED 1,379 total
includes taxes & fees
2 Nov - 3 Nov
Couples 2 Bedroom Retreat-Close to Shelburne Falls
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
27 Oct - 28 Oct
Charming 2-bedroom house in beautiful countryside of Cummington, Ma
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
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.
Sun Filled Lenox Retreat - Minutes to Tanglewood!
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
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 1,826 total
includes taxes & fees
27 Oct - 28 Oct
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Historic Berkshires Home Near Tanglewood, Trails & Wineries
9.0 out of 10, Wonderful, (19)
"It was great - just what we were looking for. "
United States
Kaye S.
The price is AED 595
AED 1,493 total
includes taxes & fees
26 Oct - 27 Oct
Historic Berkshires Home Near Tanglewood, Trails & Wineries
Bungalow in the Berkshires
10.0 out of 10, Exceptional, (4)
"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
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
FaLL Western Mass Getaway-Airhockey-Firepit
9.8 out of 10, Exceptional, (37)
"Great place and convenient to get to and from Berkshire East."
United States
Jeffrey B.
The price is AED 1,726
AED 3,176 total
includes taxes & fees
7 Nov - 8 Nov
FaLL Western Mass Getaway-Airhockey-Firepit
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.
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
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 1,653
AED 3,048 total
includes taxes & fees
2 Nov - 3 Nov
Spacious 5-bedroom house in charming Lee with WiFi
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 Windsor Hotel Reviews