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Search results; Over 1,000 homes in Tolland

Guest favourite
Home in Tolland
Private Woodland Retreat by Lake | Berkshires
3 bedrooms, 3 beds, 2 private bathrooms
11–16 Sept
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4.83 out of 5 average rating, 6 reviews
Top guest favourite
Home in Tolland
Lakefront Retreat at Porcupine Place
3 bedrooms, 4 beds, 1.5 bathrooms
28 Sept – 3 Oct
5.0 out of 5 average rating, 47 reviews
Guest favourite
Home in Tolland
Cabin with Hot Tub and Lake Access
2 bedrooms, 5 beds, 2 bathrooms
11–16 Sept
4.9 out of 5 average rating, 20 reviews
Guest favourite
Home in Tolland
Berkshires Cabin: Lake Beach Hot Tub - TheWildeBNB
2 bedrooms, 5 beds, 1 bathroom
9–14 Sept
4.97 out of 5 average rating, 31 reviews
Top guest favourite
Cabin in Sandisfield
Berkshires Cabin in Woods with Mountain Views
3 bedrooms, 3 beds, 1.5 bathrooms
26 Sept – 1 Oct
4.99 out of 5 average rating, 138 reviews
Guest favourite
Cottage in Sandisfield
Charming Cottage on Stunning Private Lake
4 bedrooms, 5 beds, 2.5 bathrooms
12–17 Sept
4.98 out of 5 average rating, 47 reviews
Top guest favourite
Home in Otis
Idyllic family retreat - spacious lake home,
4 bedrooms, 5 beds, 2.5 bathrooms
27 Oct – 1 Nov
4.95 out of 5 average rating, 175 reviews
Top guest favourite
Home in Otis
Newly rebuilt waterfront house on Otis Reservoir
4 bedrooms, 6 beds, 2.5 bathrooms
13–18 Sept
4.82 out of 5 average rating, 82 reviews
Top guest favourite
Home in Colebrook
Stunning Views of the Berkshire Foothills
3 bedrooms, 4 beds, 2.5 bathrooms
17–22 Sept
5.0 out of 5 average rating, 33 reviews
Top guest favourite
Cottage in Monterey
Beaver Lodge
3 bedrooms, 3 queen beds, 1.5 bathrooms
10–15 Sept
5.0 out of 5 average rating, 83 reviews
Guest favourite
Cottage in Otis
The lake house
3 bedrooms, 5 beds, 1 bathroom
15–20 Sept
4.96 out of 5 average rating, 51 reviews
Top guest favourite
Farm stay in Blandford
Freeland Brook Farm - magical Berkshires view
3 bedrooms, 4 beds, 2.5 bathrooms
28 Sept – 3 Oct
5.0 out of 5 average rating, 65 reviews
Guest favourite
Cabin in Colebrook
Rustic Pond Cabin: Nature, Stars & Serenity
2 bedrooms, 2 beds, 1.5 bathrooms
20–25 Oct
4.95 out of 5 average rating, 129 reviews
Guest favourite
Home in Winchester
Highland Lakefront Retreat
4 bedrooms, 5 beds, 2 bathrooms
4–9 Oct
4.89 out of 5 average rating, 47 reviews
Top guest favourite
Home in Otis
The Pinnacle House at Otis Ridge Ski Area!
4 bedrooms, 6 beds, 2 bathrooms
22–27 Sept
4.92 out of 5 average rating, 178 reviews
Top guest favourite
Home in Barkhamsted
3BR Family friendly home in Riverton paradise
3 bedrooms, 5 beds, 2 bathrooms
11–16 Sept
4.95 out of 5 average rating, 38 reviews
Top guest favourite
Home in Sandisfield
Lux on the River near Tanglewood w/220v EV charge
2 bedrooms, 2 beds, 1 bathroom
4–9 Dec
4.95 out of 5 average rating, 95 reviews
Guest favourite
Home in Otis
Home In Otis
3 bedrooms, 6 beds, 2 bathrooms
20–25 Sept
4.92 out of 5 average rating, 53 reviews
Superhost
Home in Becket
Lake front retreat - Stylish Berkshire home
4 bedrooms, 5 beds, 2 bathrooms
9–14 Sept
4.92 out of 5 average rating, 180 reviews