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Search results; Over 1,000 homes in Florida

Guest favourite
Flat in North Adams
Berkshire Mountain Top Chalet
3 bedrooms, 4 beds, 2 bathrooms
13–18 Sept
4.94 out of 5 average rating, 192 reviews
Top guest favourite
Cabin in Florida
The Greylock Cabin
2 bedrooms, 2 beds, 1 bathroom
18–23 Oct
4.99 out of 5 average rating, 86 reviews
Top guest favourite
Cabin in Florida
Lux Berkshires Mtn Cabin: Near MassMOCA & Williams
2 bedrooms, 3 beds, 1 bathroom
20–25 Sept
5.0 out of 5 average rating, 26 reviews
Top guest favourite
Barn in Florida
The Red Barn- close to ski mountains & museums
1 bedroom, 2 beds, 1 bathroom
8–13 Oct
4.96 out of 5 average rating, 96 reviews
Top guest favourite
Home in Charlemont
Tall Pines Rental | Pet Friendly | Fire Pit | Yard
3 bedrooms, 6 beds, 2 bathrooms
14–19 Sept
4.96 out of 5 average rating, 80 reviews
Top guest favourite
Home in Adams
Beautiful Victorian. The heart of the Berkshires.
5 bedrooms, 6 beds, 2 bathrooms
12–17 Sept
4.91 out of 5 average rating, 149 reviews
Holiday home in Monroe
Family Home in the mountains. Get out and explore!
4 bedrooms, 7 beds, 2 bathrooms
13–18 Sept
4.92 out of 5 average rating, 59 reviews
Home in North Adams
Scandinavian Berkshire Cottage Near MASS MoCA
3 bedrooms, 4 beds, 2 bathrooms
13–18 Oct
Guest favourite
Home in North Adams
Brooklyn Zoo: Unique retreat in the Berkshires
4 bedrooms, 5 beds, 2 bathrooms
26–31 Oct
4.94 out of 5 average rating, 283 reviews
Top guest favourite
Home in Rowe
Breezy Acres
3 bedrooms, 5 beds, 1.5 bathrooms
13–18 Sept
4.93 out of 5 average rating, 29 reviews
Guest favourite
Home in North Adams
Central Haus (Cozy Group Getaway)
4 bedrooms, 5 beds, 1.5 bathrooms
10–15 Nov
4.89 out of 5 average rating, 157 reviews
Guest favourite
Farm stay in Rowe
Maple House B&B - *Full Apartment*
3 bedrooms, 6 beds, 3 bathrooms
11–16 Sept
4.91 out of 5 average rating, 33 reviews
Home in Clarksburg
Secluded Mountain Retreat • Family & Group Getaway
4 bedrooms, 9 queen beds, 2.5 bathrooms
11–16 Sept
5.0 out of 5 average rating, 4 reviews
Guest favourite
Home in Monroe
The Camp
4 bedrooms, 7 beds, 1 bathroom
18–23 Sept
4.87 out of 5 average rating, 46 reviews
Top guest favourite
Chalet in Stamford
Peaceful VT Chalet w/ Mountain View’s
3 bedrooms, 3 beds, 2.5 bathrooms
11–16 Sept
4.94 out of 5 average rating, 132 reviews
Top guest favourite
Flat in North Adams
Berkshire Perch
3 bedrooms, 4 beds, 1 bathroom
23–28 Sept
5.0 out of 5 average rating, 28 reviews
Guest favourite
Home in Whitingham
Vermont lake house near Mt. Snow-fab 360 views!
4 bedrooms, 4 beds, 2 bathrooms
13–18 Sept
4.91 out of 5 average rating, 121 reviews
Guest favourite
Cabin in Plainfield
Camp on Windsor Pond- Berkshires
3 bedrooms, 3 beds, 1 bathroom
13–18 Sept
4.7 out of 5 average rating, 101 reviews