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Search results; Over 1,000 places in Windsor

Guest favourite
Room in Dalton
Stay with MaryHosting for 5 years,
Mother in Law unit in Dalton
20–25 Apr
4.96 out of 5 average rating, 137 reviews
Superhost
Home in Dalton
Private & Stylish Berkshires House for All Seasons
5 beds
21–26 Apr
4.89 out of 5 average rating, 80 reviews
Cottage in Plainfield
Windsor Pond spacious get-away cottage
4 beds
1–6 Jun
4.8 out of 5 average rating, 40 reviews
Cabin in Plainfield
Camp on Windsor Pond- Berkshires
1–6 May
4.52 out of 5 average rating, 25 reviews
Home in Cummington
Massachusetts Vacation Rental w/ Deck & Grill
5 beds
22–27 Apr
4.71 out of 5 average rating, 7 reviews
Boutique hotel in Lenox
Standard King in Boutique Lenox Hotel
1 king bed
19–24 Apr
4.62 out of 5 average rating, 262 reviews
Room in Pittsfield
Stay with Julia
No Clean Fee! Upper North St Lodge Room
19–24 Apr
4.62 out of 5 average rating, 37 reviews
Guest favourite
Flat in Plainfield
Sunny, light filled loft in 1873 Colonial
1 bed
19–24 Apr
4.97 out of 5 average rating, 238 reviews
Guest favourite
Cabin in Hinsdale
Beautiful 2-BR + Loft w/ Hot Tub at Lake Ashmere
4 beds
24–29 Apr
4.9 out of 5 average rating, 70 reviews
Superhost
Home in Dalton
The Yellow House
2 beds
28 Apr – 3 May
4.88 out of 5 average rating, 113 reviews
Guest favourite
Flat in Plainfield
Sunny carriage house apartment
2 beds
1–6 May
4.95 out of 5 average rating, 237 reviews
Superhost
Boutique hotel in Cummington
Singing Bridge Harmony Room
1 queen bed
20–25 Apr
4.81 out of 5 average rating, 80 reviews
Guest favourite
Room in Cummington
Stay with Kathy
Spacious private BR with king bed in Cummington!
19–24 Apr
4.92 out of 5 average rating, 26 reviews
Guest favourite
Cabin in Savoy
The Camp - 20 Minutes to Berkshire East!
1 queen bed
7–12 May
4.98 out of 5 average rating, 186 reviews
Cabin in Plainfield
Peaceful Cabin in the Woods
2 king beds
21–26 Apr
4.91 out of 5 average rating, 106 reviews
Superhost
Home in Dalton
Brooksong, the perfect Berkshires getaway
7 beds
25–30 Apr
4.92 out of 5 average rating, 170 reviews
Home in Cummington
River Forest House
3 beds
1–6 May
4.82 out of 5 average rating, 55 reviews
Guest favourite
Farm stay in Peru
The Inn at Berkshire Farm Sanctuary
4 beds
21–26 Apr
4.97 out of 5 average rating, 39 reviews