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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
$1,203 SGD
Show price breakdown
for 5 nights
$1,203 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
$1,356 SGD
Show price breakdown
for 5 nights
$1,356 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
$1,274 SGD
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for 5 nights
$1,274 SGD for 5 nights
4.9 out of 5 average rating, 10 reviews
4.9 (10)
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
$7,667 SGD
Show price breakdown
for 5 nights
$7,667 SGD for 5 nights
Free cancellation
New place to stay
New
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
$2,515 SGD
Show price breakdown
for 5 nights
$2,515 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 10 reviews
5.0 (10)
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
25–30 Oct
25–30 Oct
$1,834 SGD
$1,467 SGD
Show price breakdown
for 5 nights
Free cancellation
New place to stay
New
Photo 1 of 29
Top guest favourite
Guest favourite
Home in Marlborough
4 BR Monadnock View Luxury Chalet
4 bedrooms
4 bedrooms
,
·
5 beds
5 beds
,
·
5.5 bathrooms
5.5 bathrooms
4–9 Oct
4–9 Oct
$4,402 SGD
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for 5 nights
$4,402 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 26 reviews
5.0 (26)
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
$2,497 SGD
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for 7 nights
$2,497 SGD for 7 nights
Free cancellation
4.88 out of 5 average rating, 32 reviews
4.88 (32)
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
$2,524 SGD
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for 5 nights
$2,524 SGD for 5 nights
4.9 out of 5 average rating, 106 reviews
4.9 (106)
Photo 1 of 29
Top guest favourite
Guest favourite
Cabin in Guilford
Cozy Loft Cabin in Vermont with Sauna
3 bedrooms
3 bedrooms
,
·
7 beds
7 beds
,
·
1 bathroom
1 bathroom
1–6 Oct
1–6 Oct
$1,917 SGD
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for 5 nights
$1,917 SGD for 5 nights
5.0 out of 5 average rating, 34 reviews
5.0 (34)
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
$2,141 SGD
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for 5 nights
$2,141 SGD for 5 nights
Free cancellation
4.98 out of 5 average rating, 47 reviews
4.98 (47)
Photo 1 of 29
Home in Royalston
Historic Home w/ Modern Updates on < 4 Acres
4 bedrooms
4 bedrooms
,
·
5 beds
5 beds
,
·
2 bathrooms
2 bathrooms
11–16 Oct
11–16 Oct
$2,517 SGD
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for 5 nights
$2,517 SGD for 5 nights
4.94 out of 5 average rating, 77 reviews
4.94 (77)
Photo 1 of 29
Guest favourite
Guest favourite
Home in West Brattleboro
Private Brookside Farmhouse
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
1.5 bathrooms
1.5 bathrooms
13–18 Oct
13–18 Oct
$1,322 SGD
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for 5 nights
$1,322 SGD for 5 nights
4.93 out of 5 average rating, 88 reviews
4.93 (88)
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
$1,502 SGD
Show price breakdown
for 5 nights
$1,502 SGD for 5 nights
Free cancellation
4.94 out of 5 average rating, 77 reviews
4.94 (77)
Photo 1 of 29
Guest favourite
Guest favourite
Flat in Dummerston
1850’s Barn Retreat
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
26–31 Oct
26–31 Oct
$1,089 SGD
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for 5 nights
$1,089 SGD for 5 nights
4.91 out of 5 average rating, 516 reviews
4.91 (516)
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
$914 SGD
Show price breakdown
for 5 nights
$914 SGD for 5 nights
Free cancellation
New place to stay
New
Photo 1 of 29
Top guest favourite
Guest favourite
Home in Brattleboro
Forest Green Retreat
2 bedrooms
2 bedrooms
,
·
2 king beds
2 king beds
,
·
1 bathroom
1 bathroom
1–6 Oct
1–6 Oct
$3,961 SGD
Show price breakdown
for 5 nights
$3,961 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 6 reviews
5.0 (6)
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
$1,342 SGD
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for 5 nights
$1,342 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 6 reviews
5.0 (6)
Photo 1 of 29
Top guest favourite
Guest favourite
Home in Sunderland
Farmhouse on working dairy farm
4 bedrooms
4 bedrooms
,
·
6 beds
6 beds
,
·
1.5 bathrooms
1.5 bathrooms
4–9 Oct
4–9 Oct
$2,805 SGD
Show price breakdown
for 5 nights
$2,805 SGD for 5 nights
Free cancellation
4.98 out of 5 average rating, 66 reviews
4.98 (66)
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