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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
20–25 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
28 Sept – 3 Oct
5.0 out of 5 average rating, 47 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
Guest favourite
Home in Tolland
Cozy Berkshires Lakefront Cottage! NEW
2 bedrooms, 10 beds, 2.5 bathrooms
3–8 Jan
4.9 out of 5 average rating, 39 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
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
Cottage in Otis
Berkshire lakefront cabin with modern luxuries
3 bedrooms, 4 beds, 2 bathrooms
12–17 Sept
4.98 out of 5 average rating, 94 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
Guest favourite
Cabin in Sandisfield
Cozy Cabin in the Berkshires
2 bedrooms, 6 beds, 2 bathrooms
12–17 Sept
4.83 out of 5 average rating, 24 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
Home in Otis
Ridge House at Otis Ridge Ski Area
3 bedrooms, 5 beds, 1.5 bathrooms
24–29 Sept
4.98 out of 5 average rating, 56 reviews
Guest favourite
Home in Colebrook
Log Cabin sleeps 30 bunk style on 350 acres
30 single beds, 2 bathrooms
26–31 Oct
4.96 out of 5 average rating, 82 reviews
Guest favourite
Treehouse in New Marlborough
Berkshire Treehouse Retreat
3 bedrooms, 4 beds, WC
12–17 Sept
4.9 out of 5 average rating, 178 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 Litchfield County
70's Retro House
2 bedrooms, 2 queen beds, 2 bathrooms
14–19 Sept
4.97 out of 5 average rating, 29 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
Top guest favourite
Cottage in Becket
Berkshires Cottage by Lake. Year Round Adventures.
2 bedrooms, 2 double beds, 1 bathroom
26 Sept – 1 Oct
4.95 out of 5 average rating, 320 reviews
Guest favourite
Home in Winsted
Spacious & serene house in Berkshires
4 bedrooms, 5 beds, 3.5 bathrooms
20–25 Sept
4.92 out of 5 average rating, 25 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, 236 reviews