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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

10–15 Sept

$1,496 SGD for 5 nights

,

4.9 out of 5 average rating, 20 reviews

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Top guest favourite

Home in Tolland

Lakefront Retreat at Porcupine Place

3 bedrooms, 4 beds

8–13 Sept

$2,295 SGD for 5 nights

5.0 out of 5 average rating, 46 reviews

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Guest favourite

Home in Tolland

Private Woodland Retreat by Lake | Berkshires

3 bedrooms

6–11 Sept

$1,393 SGD for 5 nights

4.8 out of 5 average rating, 5 reviews

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Guest favourite

Home in Tolland

Cozy Berkshires Lakefront Cottage! NEW

2 bedrooms, 10 beds

3–8 Jan

$2,968 SGD for 5 nights

Free cancellation

4.89 out of 5 average rating, 37 reviews

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Top guest favourite

Home in Otis

The Berkshires Fall/Ski House - Stunning sunrise!

4 bedrooms, 10 beds

1–6 Sept

$12,061 SGD for 5 nights

5.0 out of 5 average rating, 24 reviews

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Guest favourite

Home in Tolland

Berkshires Cabin: Lake Beach Hot Tub - TheWildeBNB

2 bedrooms, 5 beds

7–13 Sept

$2,744 SGD for 6 nights

4.97 out of 5 average rating, 29 reviews

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Top guest favourite

Cottage in Otis

Berkshire lakefront cabin with modern luxuries

3 bedrooms, 4 beds

21–26 Sept

$3,992 SGD for 5 nights

4.98 out of 5 average rating, 92 reviews

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Top guest favourite

Home in Otis

Modern Berkshires Cottage w/ AC and Gas Fireplace

2 bedrooms, 7 beds

8–13 Sept

4.99 out of 5 average rating, 74 reviews

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Guest favourite

Home in Otis

Home In Otis

3 bedrooms, 6 beds

20–25 Sept

4.98 out of 5 average rating, 51 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

4–9 Dec

Free cancellation

4.95 out of 5 average rating, 93 reviews

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Guest favourite

Cottage in Otis

The lake house

3 bedrooms, 5 beds

7–12 Sept

$1,763 SGD for 5 nights

Free cancellation

4.96 out of 5 average rating, 49 reviews

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Home in Otis

Spacious cozy home in Otis

4 bedrooms, 7 beds

9–14 Sept

$2,630 SGD for 5 nights

5.0 out of 5 average rating, 3 reviews

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Top guest favourite

Cabin in Sandisfield

Berkshires Cabin in Woods with Mountain Views

3 bedrooms, 3 beds

2–7 Sept

4.99 out of 5 average rating, 138 reviews

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Top guest favourite

Cottage in Otis

Lake Escape: Lakefront Cottage in the Berkshires

2 bedrooms, 4 beds

29 Sept – 4 Oct

$2,416 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 32 reviews

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Home in Otis

Berkshire Retreat with Fenced Yard on 9 Acres

3 bedrooms, 3 beds

13–18 Sept

$1,906 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 3 reviews

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Guest favourite

Home in Torrington

Enjoy the NW Hills, then relax by the river…

3 bedrooms, 4 beds

20–25 Sept

$1,588 SGD for 5 nights

Free cancellation

4.95 out of 5 average rating, 19 reviews

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Top guest favourite

Home in Litchfield County

70's Retro House

2 bedrooms, 2 queen beds

14–19 Sept

4.96 out of 5 average rating, 28 reviews

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Top guest favourite

Chalet in Otis

Berkshire Fall Chalet | Sauna, Lake & Firepit

5 bedrooms, 8 beds

1–6 Sept

4.92 out of 5 average rating, 98 reviews

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Guest favourite

Treehouse in New Marlborough

Berkshire Treehouse Retreat

3 bedrooms, 4 beds

6–11 Sept

Free cancellation

4.9 out of 5 average rating, 176 reviews