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Vacation Homes in Windsor
Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!
Sherwood Forest
10.0 out of 10, Exceptional, (4)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
Sharon K.
$337 nightly
The price is $376
Dec 8 - Dec 9
Total with taxes and fees
Florida Mountain Log Cabin
Florida
10.0 out of 10, Exceptional, (4)
"Place was super clean. Beds were comfortable. Location was great."
Tristan e.
$316 nightly
The price is $339
Dec 4 - Dec 5
Total with taxes and fees
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking
Sherwood Forest
9.6 out of 10, Exceptional, (10)
"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."
James D.
$351 nightly
The price is $392
Dec 15 - Dec 16
Total with taxes and fees
Couples 2 Bedroom Retreat-Close to Shelburne Falls
Colrain
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. "
KayKay S.
$326 nightly
The price is $364
Dec 4 - Dec 5
Total with taxes and fees
FaLL Western Mass Getaway-Airhockey-Firepit
Colrain
9.8 out of 10, Exceptional, (38)
"Great place and convenient to get to and from Berkshire East."
Jeffrey B.
$567 nightly
The price is $633
Dec 4 - Dec 5
Total with taxes and fees
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. "
Jacklyn D.
$474 nightly
The price is $531
Dec 9 - Dec 10
Total with taxes and fees
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. "
Kaye S.
$431 nightly
The price is $483
Dec 4 - Dec 5
Total with taxes and fees
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Pittsfield
7.8 out of 10, Good, (6)
"Very clean and spacious! We enjoyed our stay with our small pup!"
Ann C.
$441 nightly
The price is $493
Dec 5 - Dec 6
Total with taxes and fees
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.
Top Windsor Hotel Reviews
Hotel Downstreet, an Ascend Collection Hotel
10/10 Excellent
Find out more about Windsor
Windsor Vacation Homes information
Number of reviews | 219 |
|---|---|
Accommodation | 273 Vacation Homes |
Lowest Price | $339 |
Highest Price | $1,111 |
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