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Search results; Over 1,000 homes in Tolland

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Guest favourite
Home in Tolland
Cabin with Hot Tub and Lake Access
2 bedrooms, 5 beds, 2 private bathrooms
28 Sept – 3 Oct
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4.9 out of 5 average rating, 21 reviews
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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
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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
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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
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Superhost
Home in Otis
Home In Otis
3 bedrooms, 6 beds, 2 bathrooms
20–25 Sept
4.93 out of 5 average rating, 55 reviews
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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
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Top guest favourite
Cottage in Otis
Berkshire lakefront cabin with modern luxuries
3 bedrooms, 4 beds, 2 bathrooms
13–18 Oct
4.98 out of 5 average rating, 94 reviews
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Top guest favourite
Home in Otis
Newly rebuilt waterfront house on Otis Reservoir
4 bedrooms, 6 beds, 2.5 bathrooms
18–23 Oct
4.81 out of 5 average rating, 83 reviews
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Guest favourite
Cottage in Otis
The lake house
3 bedrooms, 5 beds, 1 bathroom
19–24 Sept
4.96 out of 5 average rating, 52 reviews
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Superhost
Cabin in Sandisfield
The Lucas Cabin-Cozy Riverfront Getaway
2 bedrooms, 4 double beds, 2 bathrooms
27 Sept – 2 Oct
New place to stay
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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
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Guest favourite
Treehouse in New Marlborough
Berkshire Treehouse Retreat
3 bedrooms, 4 beds, WC
21–26 Sept
4.91 out of 5 average rating, 180 reviews
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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, 140 reviews
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Top guest favourite
Home in Monterey
Berkshires Retreat | Fall Foliage | Fenced Yard
5 bedrooms, 7 beds, 3.5 bathrooms
19–24 Sept
5.0 out of 5 average rating, 50 reviews
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Top guest favourite
Home in Litchfield County
70's Retro House
2 bedrooms, 2 queen beds, 2 bathrooms
19–24 Sept
4.97 out of 5 average rating, 29 reviews
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Top guest favourite
Guest suite in Norfolk
The Nest at Lovers Lane
2 bedrooms, 5 beds, 1 bathroom
20–25 Sept
4.99 out of 5 average rating, 79 reviews
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Guest favourite
Home in Becket
HOT TUB! Dog & Family Friendly in the Berkshires!
2 bedrooms, 4 beds, 1 bathroom
18–23 Oct
4.94 out of 5 average rating, 135 reviews
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Home in Otis
Spacious cozy home in Otis
4 bedrooms, 7 beds, 2.5 bathrooms
11–16 Oct
5.0 out of 5 average rating, 3 reviews
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Top guest favourite
Home in Great Barrington
Berkshires Black Abbey
3 bedrooms, 4 beds, 3 bathrooms
20–25 Sept
5.0 out of 5 average rating, 47 reviews