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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, 1.5 bathrooms
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, 2 bathrooms
6–11 Sept
4.8 out of 5 average rating, 5 reviews
Top guest favourite
Home in Barkhamsted
2BR Family friendly home in Riverton paradise
2 bedrooms, 2 beds, 2 bathrooms
12–17 Sept
4.9 out of 5 average rating, 51 reviews
Top guest favourite
Cabin in Sandisfield
Berkshires Cabin in Woods with Mountain Views
3 bedrooms, 3 beds, 1.5 bathrooms
2–7 Sept
4.99 out of 5 average rating, 138 reviews
Top guest favourite
Home in Otis
Modern Berkshires Cottage w/ AC and Gas Fireplace
2 bedrooms, 7 beds, 2 bathrooms
8–13 Sept
4.99 out of 5 average rating, 74 reviews
Guest favourite
Home in Tolland
Berkshires Cabin: Lake Beach Hot Tub - TheWildeBNB
2 bedrooms, 5 beds, 1 bathroom
7–13 Sept
4.97 out of 5 average rating, 30 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
Home in Otis
The Berkshires Fall/Ski House - Stunning sunrise!
4 bedrooms, 10 beds, 4.5 bathrooms
2–7 Sept
5.0 out of 5 average rating, 24 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
Home in Otis
Home In Otis
3 bedrooms, 6 beds, 2 bathrooms
20–25 Sept
4.94 out of 5 average rating, 52 reviews
Top guest favourite
Home in Otis
Private Mountain Retreat - Near lakes/Tanglewood
4 bedrooms, 6 beds, 3 bathrooms
13–18 Sept
5.0 out of 5 average rating, 19 reviews
Guest favourite
Cottage in Otis
The lake house
3 bedrooms, 5 beds, 1 bathroom
7–12 Sept
4.96 out of 5 average rating, 50 reviews
Top guest favourite
Home in Sheffield
Belle Meade
2 bedrooms, 2 beds, 2 bathrooms
8–13 Dec
4.99 out of 5 average rating, 133 reviews
Guest favourite
Home in Becket
HOT TUB! Dog & Family Friendly in the Berkshires!
2 bedrooms, 4 beds, 1 bathroom
25–30 Oct
4.94 out of 5 average rating, 134 reviews
Top guest favourite
Home in Otis
Ridge House at Otis Ridge Ski Area
3 bedrooms, 5 beds, 1.5 bathrooms
2–7 Sept
4.98 out of 5 average rating, 55 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, 46 reviews
Top guest favourite
Home in Otis
Newly rebuilt waterfront house on Otis Reservoir
4 bedrooms, 6 beds, 2.5 bathrooms
6–11 Sept
4.81 out of 5 average rating, 81 reviews
Guest favourite
Home in Becket
Real Estate:Therapy - Lake, Laundry, Love it
3 bedrooms, 4 beds, 1 bathroom
16–21 Sept
4.88 out of 5 average rating, 377 reviews