%{visible} of %{smart_count_str} Airbnb Category showing||||%{visible} of %{smart_count_str} Airbnb Categories showing

Search results; Over 1,000 places in Windsor

Learn how we sort results
Cabin in Plainfield
Camp on Windsor Pond- Berkshires
3 beds
1–6 May
4.52 out of 5 average rating, 25 reviews
Guest favourite
Room in Dalton
Stay with MaryHosting for 5 years,
Mother in Law unit in Dalton
1–6 Apr
4.96 out of 5 average rating, 137 reviews
Cottage in Plainfield
Windsor Pond spacious get-away cottage
4 beds
10–15 May
4.8 out of 5 average rating, 40 reviews
Cabin in Plainfield
Peaceful Cabin in the Woods
2 king beds
1–6 Apr
4.9 out of 5 average rating, 103 reviews
Home in Cummington
Massachusetts Vacation Rental w/ Deck & Grill
Professional Host
1–6 Apr
4.71 out of 5 average rating, 7 reviews
Superhost
Home in Dalton
Private & Stylish Berkshires House for All Seasons
Individual Host
1–6 Apr
4.89 out of 5 average rating, 80 reviews
Guest favourite
Flat in Plainfield
Sunny, light filled loft in 1873 Colonial
Individual Host
1–6 Apr
4.97 out of 5 average rating, 237 reviews
Guest favourite
Home in Ashfield
An 18th century farmhouse
2 beds
1–6 Apr
5.0 out of 5 average rating, 5 reviews
Superhost
Home in Dalton
Brooksong, the perfect Berkshires getaway
Individual Host
2–7 Apr
4.92 out of 5 average rating, 169 reviews
Home in Cummington
River Forest House
3 beds
26 Apr – 1 May
4.82 out of 5 average rating, 55 reviews
Guest favourite
Cabin in Hinsdale
Beautiful 2-BR + Loft w/ Hot Tub at Lake Ashmere
4 beds
1–7 Apr
4.9 out of 5 average rating, 69 reviews
Guest favourite
Cabin in Savoy
The Camp - 20 Minutes to Berkshire East!
Individual Host
7–12 May
4.98 out of 5 average rating, 184 reviews
Guest favourite
Home in Hinsdale
Berkshire Lake Retreat
Individual Host
1–6 Apr
4.94 out of 5 average rating, 49 reviews
Guest favourite
Home in Adams
Mountain View Hideaway
Individual Host
3–8 Apr
4.91 out of 5 average rating, 64 reviews
Guest favourite
Farm stay in Peru
The Inn at Berkshire Farm Sanctuary
Individual Host
1–6 Apr
4.97 out of 5 average rating, 38 reviews
Superhost
Cottage in Lanesborough
Wildlife Lakeside Cottage
Individual Host
2–7 Apr
4.85 out of 5 average rating, 248 reviews
Guest favourite
Cottage in Hinsdale
Berkshires - Charming Lakefront Cottage
Individual Host
12–17 May
4.97 out of 5 average rating, 68 reviews
Superhost
Cabin in Hinsdale
Relaxing Berkshire cabin on Lake Ashmere
3 beds
1–6 Apr
4.97 out of 5 average rating, 31 reviews