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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
$1,354 SGD
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for 5 nights
$1,354 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
$1,272 SGD
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for 5 nights
$1,272 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
$3,031 SGD
$2,512 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 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
1–6 Oct
1–6 Oct
$733 SGD
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for 5 nights
$733 SGD for 5 nights
Free cancellation
4.95 out of 5 average rating, 195 reviews
4.95 (195)
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
1–6 Oct
1–6 Oct
$7,657 SGD
$6,126 SGD
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for 5 nights
Free cancellation
New place to stay
New
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
$1,832 SGD
$1,465 SGD
Show price breakdown
for 5 nights
Free cancellation
New place to stay
New
Photo 1 of 12
Guest favourite
Guest favourite
Flat in Hinsdale
Welcome to the Kilburn House!
6 beds
6 beds
,
·
1 bathroom
1 bathroom
14–19 Oct
14–19 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 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
1–6 Oct
1–6 Oct
$2,009 SGD
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for 5 nights
$2,009 SGD for 5 nights
Free cancellation
4.98 out of 5 average rating, 46 reviews
4.98 (46)
Photo 1 of 6
Guest favourite
Guest favourite
Room in Chesterfield
Waterfront Paradise - 1.3 mile to Brattleboro
2 beds
2 beds
,
·
1 bathroom
1 bathroom
1–6 Oct
1–6 Oct
$940 SGD
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for 5 nights
$940 SGD for 5 nights
Free cancellation
4.93 out of 5 average rating, 69 reviews
4.93 (69)
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
$2,494 SGD
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for 7 nights
$2,494 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
Farm stay in Warwick
Be Still Meadows at Chase Hill Farm - entire home
3 bedrooms
3 bedrooms
,
·
5 beds
5 beds
,
·
2 bathrooms
2 bathrooms
11–16 Oct
11–16 Oct
$2,232 SGD
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for 5 nights
$2,232 SGD for 5 nights
5.0 out of 5 average rating, 36 reviews
5.0 (36)
Photo 1 of 16
Top guest favourite
Guest favourite
Place to stay in Chesterfield
The Ultimate Romantic Getaway
1 bed
1 bed
,
·
1 bathroom
1 bathroom
1–6 Oct
1–6 Oct
$1,308 SGD
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for 5 nights
$1,308 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 67 reviews
5.0 (67)
Photo 1 of 16
Guest favourite
Guest favourite
Home in Chesterfield
Lakehouse Getaway
2 bedrooms
2 bedrooms
,
·
6 beds
6 beds
,
·
1.5 bathrooms
1.5 bathrooms
1–6 Oct
1–6 Oct
$3,221 SGD
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for 5 nights
$3,221 SGD for 5 nights
5.0 out of 5 average rating, 11 reviews
5.0 (11)
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
$2,521 SGD
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for 5 nights
$2,521 SGD for 5 nights
Free cancellation
4.9 out of 5 average rating, 105 reviews
4.9 (105)
Photo 1 of 29
Guest favourite
Guest favourite
Home in Guilford
Vermont Mirror House
1 bedroom
1 bedroom
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
13–18 Nov
13–18 Nov
$2,870 SGD
$2,537 SGD
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for 5 nights
4.95 out of 5 average rating, 161 reviews
4.95 (161)
Photo 1 of 29
Home in Westmoreland
Tasteful Country Home on 5 Acres ~ 3 Mi to Lake!
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
1–6 Oct
1–6 Oct
$1,888 SGD
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for 5 nights
$1,888 SGD for 5 nights
4.93 out of 5 average rating, 14 reviews
4.93 (14)
Photo 1 of 29
Guest favourite
Guest favourite
Cottage in Chesterfield
Modern Luxury on the Lake
1 bedroom
1 bedroom
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
1–6 Oct
1–6 Oct
$3,829 SGD
Show price breakdown
for 5 nights
$3,829 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
Guest suite in Jaffrey
Comfy Quarters Suite 1
1 bedroom
1 bedroom
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
3–8 Oct
3–8 Oct
$963 SGD
$821 SGD
Show price breakdown
for 5 nights
Free cancellation
4.95 out of 5 average rating, 379 reviews
4.95 (379)
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