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Search results; 784 places in Windsor

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
Flat in Dalton
Welcome to the Shire!
1–6 May
4.8 out of 5 average rating, 5 reviews
Guest favourite
Flat in Stamford
Getaway Near Mass MoCA, Great Hiking, Scenic Views
1 queen bed
19–24 Apr
4.86 out of 5 average rating, 274 reviews
Superhost
Flat in Pittsfield
Cozy Chic - Studio Apartment
1 queen bed
6–11 May
New place to stay
Guest favourite
Flat in North Adams
See MoCA from your mansion+Sauna! Ski nearby!
4 beds
19–24 May
4.97 out of 5 average rating, 405 reviews
Guest favourite
Flat in Plainfield
Sunny carriage house apartment
2 beds
1–6 May
4.95 out of 5 average rating, 237 reviews
Guest favourite
Flat in Adams
Downtown Studio in Adams
1 bed
19–24 Apr
4.91 out of 5 average rating, 22 reviews
Flat in Pittsfield
Renovated, Spacious, and Ideal for Families
20–25 Apr
4.5 out of 5 average rating, 4 reviews
Guest favourite
Flat in Adams
Mountain Living, 1-bedroom unit, outdoor hot-tub
1 queen bed
22–27 Apr
4.88 out of 5 average rating, 57 reviews
Guest favourite
Flat in Pittsfield
Comfortable Pittsfield Loft
1 queen bed
20–25 Apr
4.92 out of 5 average rating, 25 reviews
Guest favourite
Flat in Pittsfield
Luxury 2BR Apt. Home w/Work Area
2 beds
24–29 Apr
4.96 out of 5 average rating, 52 reviews
Flat in Pittsfield
Beautiful Blue Studio downtown
1 bed
3–8 May
5.0 out of 5 average rating, 4 reviews
Superhost
Flat in Pittsfield
Sharon's Place 5 420 friendly!!!!!!
2 beds
5–12 May
4.75 out of 5 average rating, 141 reviews
Guest favourite
Flat in Shelburne Falls
Soaring 2-level loft w/ views in heart of downtown
2 beds
28 Apr – 3 May
4.94 out of 5 average rating, 145 reviews
Guest favourite
Flat in Greenfield
Mohawk Trail View/ private apt. no cleaning Fee
1 queen bed
21–26 Apr
4.96 out of 5 average rating, 267 reviews
Guest favourite
Flat in North Adams
Steps to MoCA, 2bd + SAUNA! Near Ski!
3 beds
12–17 May
4.96 out of 5 average rating, 414 reviews
Superhost
Flat in Lanesborough
Charming Apt. in 18th c. Berkshire Farmhouse
2 double beds
21–26 Apr
4.85 out of 5 average rating, 62 reviews
Superhost
Flat in Pittsfield
Cozy Studio Apt in Downtown Victorian
1 bed
19–24 Apr
4.83 out of 5 average rating, 18 reviews