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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, 47 reviews
Guest favourite
Home in Tolland
Private Woodland Retreat by Lake | Berkshires
3 bedrooms, 2 bathrooms
11–16 Sept
4.8 out of 5 average rating, 5 reviews
Guest favourite
Home in Tolland
Cozy Berkshires Lakefront Cottage! NEW
2 bedrooms, 10 beds, 2.5 bathrooms
3–8 Jan
4.89 out of 5 average rating, 38 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
Cottage in Otis
Berkshire lakefront cabin with modern luxuries
3 bedrooms, 4 beds, 2 bathrooms
7–12 Sept
4.98 out of 5 average rating, 93 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, 31 reviews
Top guest favourite
Home in Otis
Newly rebuilt waterfront house on Otis Reservoir
4 bedrooms, 6 beds, 2.5 bathrooms
13–18 Sept
4.81 out of 5 average rating, 81 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, 94 reviews
Top guest favourite
Home in Otis
The Berkshires Fall/Ski House - Stunning sunrise!
4 bedrooms, 10 beds, 4.5 bathrooms
8–13 Sept
5.0 out of 5 average rating, 24 reviews
Top guest favourite
Home in Monterey
Jaw dropping mountain & lake views
4 bedrooms, 4 beds, 2 bathrooms
8–13 Sept
4.96 out of 5 average rating, 309 reviews
Guest favourite
Home in Otis
Family Berkshires Cabin w/ Climbing Wall, Games
3 bedrooms, 7 beds, 3 bathrooms
13–18 Sept
5.0 out of 5 average rating, 13 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
Guest favourite
Cottage in Otis
The lake house
3 bedrooms, 5 beds, 1 bathroom
15–20 Sept
4.96 out of 5 average rating, 50 reviews
Guest favourite
Cabin in Otis
Enjoy 43 Acres on Two Ponds!
3 bedrooms, 6 beds, 2 bathrooms
8–13 Sept
4.89 out of 5 average rating, 70 reviews
Cottage in Becket
Lakefront | Pvt Dock | Kayaks | Firepit | 1G | W/D
3 bedrooms, 6 beds, 2 bathrooms
20–25 Sept
4.93 out of 5 average rating, 293 reviews
Top guest favourite
Home in Monterey
Beautiful family home, Hike, Fireplace, Sleeps 12
5 bedrooms, 7 beds, 2.5 bathrooms
13–18 Sept
4.96 out of 5 average rating, 234 reviews
Top guest favourite
Home in Monterey
Berkshires Retreat | Fall Foliage | Fenced Yard
5 bedrooms, 7 beds, 3.5 bathrooms
10–15 Sept
5.0 out of 5 average rating, 49 reviews
Guest favourite
Home in Winsted
Spacious & serene house in Berkshires
4 bedrooms, 5 beds, 3.5 bathrooms
15–20 Sept
4.92 out of 5 average rating, 25 reviews