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Search results; Over 1,000 homes in Winchester
Over 1,000 homes in Winchester
Photo 1 of 29
Guest favourite
Guest favourite
Chalet in Winchester
Chalet Sonsie: A Sweetwater Stay
2 bedrooms
,
·
3 beds
,
·
1.5 shared bathrooms
3–8 Nov
3–8 Nov
$1,218 SGD
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for 5 nights
$1,218 SGD for 5 nights
,
·
4.85 out of 5 average rating, 167 reviews
4.85 (167)
Photo 1 of 13
Guest favourite
Guest favourite
Cabin in Winchester
The Ironclad Mountain Retreat
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
4–9 Oct
4–9 Oct
$1,245 SGD
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for 5 nights
$1,245 SGD for 5 nights
4.83 out of 5 average rating, 60 reviews
4.83 (60)
Photo 1 of 29
Guest favourite
Guest favourite
Cottage in Winchester
The Humblebee Cottage
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
27 Sept – 2 Oct
27 Sept – 2 Oct
$1,372 SGD
$1,249 SGD
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for 5 nights
4.9 out of 5 average rating, 10 reviews
4.9 (10)
Photo 1 of 29
Guest favourite
Guest favourite
Home in Richmond
Porcupine Hill Farm
6 bedrooms
6 bedrooms
,
·
8 beds
8 beds
,
·
2 bathrooms
2 bathrooms
29 Sept – 4 Oct
29 Sept – 4 Oct
$3,031 SGD
$2,511 SGD
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for 5 nights
Free cancellation
5.0 out of 5 average rating, 9 reviews
5.0 (9)
Photo 1 of 28
Home in Chesterfield
Large Vacation Rental Nestled in 400 Acres
7 bedrooms
7 bedrooms
,
·
14 single beds
14 single beds
,
·
4 bathrooms
4 bathrooms
27 Sept – 2 Oct
27 Sept – 2 Oct
$7,656 SGD
$6,125 SGD
Show price breakdown
for 5 nights
Free cancellation
New place to stay
New
Photo 1 of 25
Guest favourite
Guest favourite
Home in Northfield
Cozy Home with Relaxing Views
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
1.5 bathrooms
1.5 bathrooms
20–27 Sept
20–27 Sept
$2,494 SGD
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for 7 nights
$2,494 SGD for 7 nights
4.88 out of 5 average rating, 32 reviews
4.88 (32)
Photo 1 of 12
Guest favourite
Guest favourite
Flat in Hinsdale
Welcome to the Kilburn House!
6 beds
6 beds
,
·
1 bathroom
1 bathroom
9–14 Oct
9–14 Oct
$760 SGD
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for 5 nights
$760 SGD for 5 nights
5.0 out of 5 average rating, 6 reviews
5.0 (6)
Photo 1 of 6
Rooms in Northfield
Deerfield King Suite at Centennial House B&B
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
20–25 Sept
20–25 Sept
$1,793 SGD
$1,435 SGD
Show price breakdown
for 5 nights
New place to stay
New
Photo 1 of 25
Top guest favourite
Guest favourite
Cottage in Orange
Lake House with view of mountain
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
20–25 May
20–25 May
$1,787 SGD
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for 5 nights
$1,787 SGD for 5 nights
Free cancellation
4.99 out of 5 average rating, 96 reviews
4.99 (96)
Photo 1 of 6
Top guest favourite
Guest favourite
Rooms in Hinsdale
Country Retreat
2 bedrooms
2 bedrooms
,
·
3 queen beds
3 queen beds
,
·
1 bathroom
1 bathroom
4–9 Jun
4–9 Jun
$1,541 SGD
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for 5 nights
$1,541 SGD for 5 nights
Free cancellation
4.95 out of 5 average rating, 57 reviews
4.95 (57)
Photo 1 of 13
Top guest favourite
Guest favourite
Flat in Vernon
Farm land view.
1 bedroom
1 bedroom
,
·
1 queen bed
1 queen bed
,
·
1 bathroom
1 bathroom
12–17 Oct
12–17 Oct
$835 SGD
$733 SGD
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for 5 nights
Free cancellation
4.95 out of 5 average rating, 195 reviews
4.95 (195)
Photo 1 of 28
Top guest favourite
Guest favourite
Home in Keene
The Brick House on Washington Street
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
1 bathroom
1 bathroom
19–24 Oct
19–24 Oct
$2,514 SGD
$2,230 SGD
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for 5 nights
Free cancellation
4.93 out of 5 average rating, 251 reviews
4.93 (251)
Photo 1 of 18
Top guest favourite
Guest favourite
Flat in Brattleboro
Charming 2BR Vermont Home • Porch • Full Kitchen
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
25–30 Oct
25–30 Oct
$1,535 SGD
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for 5 nights
$1,535 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 17 reviews
5.0 (17)
Photo 1 of 14
Guest favourite
Guest favourite
Yurt in Putney
Serene Yurt Near the Best of Southern Vermont
1 bedroom
1 bedroom
,
·
1 bed
1 bed
,
·
1 bathroom
1 bathroom
4–9 Oct
4–9 Oct
$872 SGD
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for 5 nights
$872 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 9 reviews
5.0 (9)
Photo 1 of 17
Guest favourite
Guest favourite
Tiny home in Chesterfield
Cozy Cottage on Spofford Lake
1 bedroom
1 bedroom
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
4–9 Oct
4–9 Oct
$926 SGD
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for 5 nights
$926 SGD for 5 nights
5.0 out of 5 average rating, 7 reviews
5.0 (7)
Photo 1 of 29
Guest favourite
Guest favourite
Home in Chesterfield
Beautiful Home near the sand at Spofford Lake!
2 bedrooms
2 bedrooms
,
·
6 beds
6 beds
,
·
2 bathrooms
2 bathrooms
6–11 Oct
6–11 Oct
$3,399 SGD
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for 5 nights
$3,399 SGD for 5 nights
5.0 out of 5 average rating, 19 reviews
5.0 (19)
Photo 1 of 29
Top guest favourite
Guest favourite
Guest suite in Brattleboro
Charming studio in renovated 19th century church.
2 beds
2 beds
,
·
1 bathroom
1 bathroom
1–6 Nov
1–6 Nov
$831 SGD
$729 SGD
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for 5 nights
Free cancellation
4.95 out of 5 average rating, 644 reviews
4.95 (644)
Photo 1 of 29
Guest favourite
Guest favourite
Flat in Greenfield
Treetop Haven
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
25–30 Oct
25–30 Oct
$1,253 SGD
$1,104 SGD
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for 5 nights
Free cancellation
4.92 out of 5 average rating, 51 reviews
4.92 (51)
Photo 1 of 29
Top guest favourite
Guest favourite
Cabin in West Brattleboro
Hidden Forest Cabin: Kitchen, Deck, Babbling Brook
3 bedrooms
3 bedrooms
,
·
6 beds
6 beds
,
·
1 bathroom
1 bathroom
27 Sept – 2 Oct
27 Sept – 2 Oct
$2,298 SGD
$1,708 SGD
Show price breakdown
for 5 nights
Free cancellation
4.98 out of 5 average rating, 46 reviews
4.98 (46)
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