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Search results; Over 1,000 homes in Tolland

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
20–25 Sept
4.9 out of 5 average rating, 21 reviews
Guest favourite
Home in Tolland
Private Woodland Retreat by Lake | Berkshires
3 bedrooms, 3 beds, 2 bathrooms
20–25 Sept
4.86 out of 5 average rating, 7 reviews
Superhost
Cabin in Sandisfield
The Lucas Cabin
2 bedrooms, 4 beds, 2 bathrooms
27 Sept – 2 Oct
New place to stay
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
Guest favourite
Home in Barkhamsted
2BR Family friendly home in Riverton paradise
2 bedrooms, 2 beds, 2 bathrooms
2–7 Nov
4.9 out of 5 average rating, 51 reviews
Guest favourite
Home in Sandisfield
Waterfront oasis in heart of Berkshires
4 bedrooms, 3 beds, 3 bathrooms
1–6 Nov
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, 66 reviews
Top guest favourite
Home in Otis
Newly rebuilt waterfront house on Otis Reservoir
4 bedrooms, 6 beds, 2.5 bathrooms
18–23 Oct
4.82 out of 5 average rating, 82 reviews
Top guest favourite
Home in Otis
Private Mountain Retreat Near Ski Areas
4 bedrooms, 6 beds, 3 bathrooms
16–21 Sept
5.0 out of 5 average rating, 20 reviews
Superhost
Home in Becket
Lake front retreat - Stylish Berkshire home
4 bedrooms, 5 beds, 2 bathrooms
15–20 Sept
4.92 out of 5 average rating, 180 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
Cottage in Otis
The lake house
3 bedrooms, 5 beds, 1 bathroom
15–20 Sept
4.96 out of 5 average rating, 51 reviews
Superhost
Home in Otis
Home In Otis
3 bedrooms, 6 beds, 2 bathrooms
20–25 Sept
4.93 out of 5 average rating, 54 reviews
Top guest favourite
Home in Monterey
Charming cottage w/ gorgeous views.
2 bedrooms, 2 beds, 2 bathrooms
17–22 Sept
4.93 out of 5 average rating, 373 reviews
Guest favourite
Home in Otis
Direct Lakefront Home on Otis Reservoir Giant Yard
4 bedrooms, 7 beds, 2.5 bathrooms
4–9 Oct
4.96 out of 5 average rating, 137 reviews
Top guest favourite
Cottage in Monterey
Beaver Lodge
3 bedrooms, 3 queen beds, 1.5 bathrooms
28 Sept – 3 Oct
5.0 out of 5 average rating, 83 reviews
Cottage in Becket
Lakefront | Pvt Dock | Kayaks | Firepit | 1G | W/D
3 bedrooms, 6 beds, 2 bathrooms
3–8 Oct
4.93 out of 5 average rating, 295 reviews