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Search results; Over 1,000 homes in Tolland

Guest favourite
Home in Tolland
Cabin with Hot Tub and Lake Access
2 bedrooms, 5 beds, 2 private bathrooms
10–15 Sept
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4.9 out of 5 average rating, 20 reviews
Top guest favourite
Home in Tolland
Lakefront Retreat at Porcupine Place
3 bedrooms, 4 beds
8–13 Sept
5.0 out of 5 average rating, 46 reviews
Guest favourite
Home in Tolland
Private Woodland Retreat by Lake | Berkshires
3 bedrooms
6–11 Sept
4.8 out of 5 average rating, 5 reviews
Top guest favourite
Home in Otis
Modern Berkshires Cottage w/ AC and Gas Fireplace
2 bedrooms, 7 beds
8–13 Sept
4.99 out of 5 average rating, 74 reviews
Guest favourite
Home in Barkhamsted
2BR Family friendly home in Riverton paradise
2 bedrooms, 2 beds
12–17 Sept
4.9 out of 5 average rating, 51 reviews
Guest favourite
Home in Tolland
Berkshires Cabin: Lake Beach Hot Tub - TheWildeBNB
2 bedrooms, 5 beds
7–13 Sept
4.97 out of 5 average rating, 30 reviews
Top guest favourite
Home in Colebrook
Norbrook Farm ~ Rustic farmhouse w/ pond & trails
3 bedrooms, 4 beds
27 Oct – 1 Nov
4.99 out of 5 average rating, 250 reviews
Top guest favourite
Home in Otis
The Berkshires Fall/Ski House - Stunning sunrise!
4 bedrooms, 10 beds
4–9 Sept
5.0 out of 5 average rating, 24 reviews
Top guest favourite
Home in Sandisfield
Lux on the River near Tanglewood w/220v EV charge
2 bedrooms, 2 beds
4–9 Dec
4.95 out of 5 average rating, 94 reviews
Top guest favourite
Farm stay in Blandford
Freeland Brook Farm - magical Berkshires view
3 bedrooms, 4 beds
28 Sept – 3 Oct
5.0 out of 5 average rating, 65 reviews
Top guest favourite
Home in Colebrook
Stunning Views of the Berkshire Foothills
3 bedrooms, 4 beds
17–22 Sept
5.0 out of 5 average rating, 33 reviews
Top guest favourite
Home in Otis
Ridge House at Otis Ridge Ski Area
3 bedrooms, 5 beds
4–9 Sept
4.98 out of 5 average rating, 55 reviews
Guest favourite
Home in Sandisfield
Waterfront oasis in heart of Berkshires
4 bedrooms, 3 beds
13–18 Sept
4.98 out of 5 average rating, 48 reviews
Guest favourite
Home in Becket
HOT TUB! Dog & Family Friendly in the Berkshires!
2 bedrooms, 4 beds
25–30 Oct
4.94 out of 5 average rating, 134 reviews
Top guest favourite
Home in Otis
Newly rebuilt waterfront house on Otis Reservoir
4 bedrooms, 6 beds
6–11 Sept
4.81 out of 5 average rating, 81 reviews
Guest favourite
Home in Otis
Family Berkshires Cabin w/ Climbing Wall, Games
3 bedrooms, 7 beds
8–13 Sept
5.0 out of 5 average rating, 12 reviews
Guest favourite
Home in Otis
Home In Otis
3 bedrooms, 6 beds
20–25 Sept
4.94 out of 5 average rating, 52 reviews
Top guest favourite
Cottage in Monterey
Beaver Lodge
3 bedrooms, 3 queen beds
10–15 Sept
5.0 out of 5 average rating, 83 reviews
Top guest favourite
Home in Otis
The Pinnacle House at Otis Ridge Ski Area!
4 bedrooms, 6 beds
22–27 Sept
4.92 out of 5 average rating, 178 reviews