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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
$1,223 SGD
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for 5 nights
$1,223 SGD for 5 nights
,
·
4.85 out of 5 average rating, 168 reviews
4.85 (168)
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
$1,365 SGD
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for 5 nights
$1,365 SGD for 5 nights
4.84 out of 5 average rating, 61 reviews
4.84 (61)
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
17–22 Oct
17–22 Oct
$1,276 SGD
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for 5 nights
$1,276 SGD 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
1–6 Oct
1–6 Oct
$2,519 SGD
Show price breakdown
for 5 nights
$2,519 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 10 reviews
5.0 (10)
Photo 1 of 29
Superhost
Superhost
Flat in Marlboro, Vermont
Shakespeare's Cherry Tree Cottage
1 bedroom
1 bedroom
,
·
2 queen beds
2 queen beds
,
·
1 bathroom
1 bathroom
18–23 Oct
18–23 Oct
$916 SGD
Show price breakdown
for 5 nights
$916 SGD for 5 nights
Free cancellation
New place to stay
New
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
21–26 Oct
21–26 Oct
$735 SGD
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for 5 nights
$735 SGD for 5 nights
Free cancellation
4.95 out of 5 average rating, 196 reviews
4.95 (196)
Photo 1 of 12
Guest favourite
Guest favourite
Flat in Hinsdale
Welcome to the Kilburn House!
6 beds
6 beds
,
·
1 bathroom
1 bathroom
16–21 Dec
16–21 Dec
$1,344 SGD
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for 5 nights
$1,344 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 6 reviews
5.0 (6)
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
1–8 Oct
1–8 Oct
$2,501 SGD
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for 7 nights
$2,501 SGD for 7 nights
Free cancellation
4.88 out of 5 average rating, 32 reviews
4.88 (32)
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
$928 SGD
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for 5 nights
$928 SGD for 5 nights
5.0 out of 5 average rating, 7 reviews
5.0 (7)
Photo 1 of 29
Top guest favourite
Guest favourite
Farm stay in Warwick
Be Still Meadows at Chase Hill Farm - first floor
1 bedroom
1 bedroom
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
11–16 Oct
11–16 Oct
$1,300 SGD
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for 5 nights
$1,300 SGD for 5 nights
4.97 out of 5 average rating, 77 reviews
4.97 (77)
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
14–19 Oct
14–19 Oct
$2,181 SGD
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for 5 nights
$2,181 SGD for 5 nights
Free cancellation
4.98 out of 5 average rating, 47 reviews
4.98 (47)
Photo 1 of 29
Guest favourite
Guest favourite
Place to stay in Winchendon
Enjoy your stay in an Antique Home in a Toy Museum
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
2 bathrooms
2 bathrooms
1–6 Oct
1–6 Oct
$2,528 SGD
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for 5 nights
$2,528 SGD for 5 nights
4.9 out of 5 average rating, 106 reviews
4.9 (106)
Photo 1 of 29
Guest favourite
Guest favourite
Home in Brattleboro
Bright, spacious country home
4 bedrooms
4 bedrooms
,
·
5 beds
5 beds
,
·
2 bathrooms
2 bathrooms
18–23 Oct
18–23 Oct
$2,060 SGD
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for 5 nights
$2,060 SGD for 5 nights
4.91 out of 5 average rating, 67 reviews
4.91 (67)
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
$731 SGD
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for 5 nights
$731 SGD for 5 nights
Free cancellation
4.95 out of 5 average rating, 645 reviews
4.95 (645)
Photo 1 of 29
Home in Charlemont
3 Bedroom 2 Bath Cottage on The Brook
3 bedrooms
3 bedrooms
,
·
5 beds
5 beds
,
·
2 bathrooms
2 bathrooms
1–6 Oct
1–6 Oct
$3,143 SGD
Show price breakdown
for 5 nights
$3,143 SGD for 5 nights
New place to stay
New
Photo 1 of 28
Top guest favourite
Guest favourite
Guest house in Chesterfield
House on a hill
1 bedroom
1 bedroom
,
·
1 bed
1 bed
,
·
1 bathroom
1 bathroom
27 Oct – 1 Nov
27 Oct – 1 Nov
$720 SGD
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for 5 nights
$720 SGD for 5 nights
Free cancellation
4.98 out of 5 average rating, 116 reviews
4.98 (116)
Photo 1 of 29
Top guest favourite
Guest favourite
Home in Guilford
Cozy Private Cabin in the Woods • Hemlock Haven
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
25–30 Oct
25–30 Oct
$1,422 SGD
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for 5 nights
$1,422 SGD for 5 nights
Free cancellation
4.93 out of 5 average rating, 15 reviews
4.93 (15)
Photo 1 of 27
Guest favourite
Guest favourite
Guest house in Brattleboro
Casita by the Green: Quiet, Country, close to town
1 bedroom
1 bedroom
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
1–6 Oct
1–6 Oct
$1,504 SGD
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for 5 nights
$1,504 SGD for 5 nights
Free cancellation
4.94 out of 5 average rating, 77 reviews
4.94 (77)
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
12–17 Oct
12–17 Oct
$7,680 SGD
Show price breakdown
for 5 nights
$7,680 SGD for 5 nights
Free cancellation
New place to stay
New
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