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Search results; Over 1,000 homes in Winchester

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Guest favourite

Chalet in Winchester

Chalet Sonsie: A Sweetwater Stay

2 bedrooms, 3 beds, 1.5 shared bathrooms

3–8 Nov

$1,223 SGD for 5 nights

,

4.85 out of 5 average rating, 168 reviews

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Guest favourite

Cabin in Winchester

The Ironclad Mountain Retreat

2 bedrooms, 2 beds

4–9 Oct

$1,364 SGD for 5 nights

4.84 out of 5 average rating, 61 reviews

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Guest favourite

Cottage in Winchester

The Humblebee Cottage

2 bedrooms, 3 beds

17–22 Oct

$1,276 SGD for 5 nights

4.9 out of 5 average rating, 10 reviews

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Guest favourite

Home in Richmond

Porcupine Hill Farm

6 bedrooms, 8 beds

1–6 Oct

$2,519 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 10 reviews

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Rooms in Northfield

Deerfield King Suite at Centennial House B&B

2 bedrooms, 3 beds

25–30 Oct

Free cancellation

New place to stay

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Top guest favourite

Rooms in Hinsdale

Country Retreat

2 bedrooms, 3 queen beds

4–9 Jun

$1,545 SGD for 5 nights

Free cancellation

4.95 out of 5 average rating, 57 reviews

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Home in Guilford

Writers Retreat! Peace and solitude.

1 bedroom, 1 queen bed

4–9 Oct

Free cancellation

New place to stay

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Guest favourite

Home in Northfield

Cozy Home with Relaxing Views

3 bedrooms, 3 beds

1–8 Oct

$2,501 SGD for 7 nights

Free cancellation

4.88 out of 5 average rating, 32 reviews

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Guest favourite

Place to stay in Winchendon

Enjoy your stay in an Antique Home in a Toy Museum

3 bedrooms, 3 beds

1–6 Oct

$2,528 SGD for 5 nights

4.9 out of 5 average rating, 106 reviews

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Guest favourite

Cottage in Chesterfield

Modern Luxury on the Lake

1 bedroom, 2 beds

1–6 Oct

$3,840 SGD for 5 nights

5.0 out of 5 average rating, 6 reviews

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Top guest favourite

Cabin in Guilford

Cozy Loft Cabin in Vermont with Sauna

3 bedrooms, 7 beds

1–6 Oct

$1,920 SGD for 5 nights

5.0 out of 5 average rating, 34 reviews

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Top guest favourite

Cabin in West Brattleboro

Hidden Forest Cabin: Kitchen, Deck, Babbling Brook

3 bedrooms, 6 beds

14–19 Oct

$2,181 SGD for 5 nights

Free cancellation

4.98 out of 5 average rating, 47 reviews

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Home in Royalston

Historic Home w/ Modern Updates on < 4 Acres

4 bedrooms, 5 beds

11–16 Oct

$2,521 SGD for 5 nights

4.94 out of 5 average rating, 77 reviews

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Top guest favourite

Home in Dummerston

Woodsy Retreat Near Skiing, Private Pool in Summer

2 bedrooms, 4 beds

18–23 Oct

$1,837 SGD for 5 nights

Free cancellation

4.9 out of 5 average rating, 49 reviews

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Guest favourite

Home in West Brattleboro

Private Brookside Farmhouse

3 bedrooms, 4 beds

13–18 Oct

$1,324 SGD for 5 nights

4.93 out of 5 average rating, 88 reviews

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Guest favourite

Guest house in Brattleboro

Casita by the Green: Quiet, Country, close to town

1 bedroom, 2 beds

1–6 Oct

$1,504 SGD for 5 nights

Free cancellation

4.94 out of 5 average rating, 77 reviews

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Guest favourite

Flat in Hinsdale

Welcome to the Kilburn House!

6 beds

16–21 Dec

$1,344 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 6 reviews

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Guest favourite

Flat in Dummerston

1850’s Barn Retreat

2 bedrooms, 2 beds

26–31 Oct

$1,091 SGD for 5 nights

4.91 out of 5 average rating, 516 reviews

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Top guest favourite

Home in Sunderland

Farmhouse on working dairy farm

4 bedrooms, 6 beds

4–9 Oct

$2,793 SGD for 5 nights

Free cancellation

4.98 out of 5 average rating, 66 reviews