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Search results; Over 1,000 homes in Winchester
Over 1,000 homes in Winchester
Top guest favourite
Guest favourite
Cottage in Winchester
The Little House - a historic New England cottage.
2 bedrooms
,
·
3 beds
,
·
1 private bathroom
1–6 Sept
1–6 Sept
$3,459 SGD
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for 5 nights
$3,459 SGD for 5 nights
,
·
4.95 out of 5 average rating, 86 reviews
4.95 (86)
Guest favourite
Guest favourite
Flat in Winchester
Winchester Apartment on Greenway
4.95 out of 5 average rating, 60 reviews
4.95 (60)
,
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1 bedroom
1 bedroom
,
·
1 bed
1 bed
,
·
1 bathroom
1 bathroom
10–15 Nov
10–15 Nov
$1,050 SGD
Show price breakdown
for 5 nights
$1,050 SGD for 5 nights
Free cancellation
Guest favourite
Guest favourite
Home in Winchester
3 Bedroom Boston-area Gem
4.96 out of 5 average rating, 27 reviews
4.96 (27)
,
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3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
1 bathroom
1 bathroom
14–19 Aug
14–19 Aug
$3,180 SGD
Show price breakdown
for 5 nights
$3,180 SGD for 5 nights
Free cancellation
Superhost
Superhost
Home in Winchester
Luxury Winchester Estate | 4BR + Loft | Sleeps 10
4 bedrooms
4 bedrooms
,
·
5 beds
5 beds
,
·
4.5 bathrooms
4.5 bathrooms
1–6 Aug
1–6 Aug
$7,720 SGD
$6,984 SGD
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for 5 nights
Free cancellation
Top guest favourite
Guest favourite
Flat in Woburn
Comfy-Spacious-private 1BR conveniently located
4.95 out of 5 average rating, 243 reviews
4.95 (243)
,
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1 bedroom
1 bedroom
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
10–15 Aug
10–15 Aug
$1,165 SGD
Show price breakdown
for 5 nights
$1,165 SGD for 5 nights
Free cancellation
Superhost
Superhost
Home in Melrose
Architectural Sanctuary | Sunny Modern Convenient
5.0 out of 5 average rating, 3 reviews
5.0 (3)
,
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4 bedrooms
4 bedrooms
,
·
5 beds
5 beds
,
·
1.5 bathrooms
1.5 bathrooms
6–11 Aug
6–11 Aug
$3,684 SGD
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for 5 nights
$3,684 SGD for 5 nights
Guest favourite
Guest favourite
Guest suite in Arlington
3 Bedroom 2nd Floor Unit - commute to Boston
4.88 out of 5 average rating, 52 reviews
4.88 (52)
,
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3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
6–11 Aug
6–11 Aug
$1,547 SGD
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for 5 nights
$1,547 SGD for 5 nights
Free cancellation
Top guest favourite
Guest favourite
Home in Medford
Bright Family Oasis Near Boston w/ Parking
4.99 out of 5 average rating, 119 reviews
4.99 (119)
,
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3 bedrooms
3 bedrooms
,
·
5 beds
5 beds
,
·
1.5 bathrooms
1.5 bathrooms
12–17 Aug
12–17 Aug
$3,234 SGD
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for 5 nights
$3,234 SGD for 5 nights
Top guest favourite
Guest favourite
Room in Arlington
Comfortable room with private access
4.94 out of 5 average rating, 18 reviews
4.94 (18)
,
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1 bed
1 bed
,
·
1.5 bathrooms
1.5 bathrooms
5–10 Aug
5–10 Aug
$701 SGD
Show price breakdown
for 5 nights
$701 SGD for 5 nights
Free cancellation
Guest favourite
Guest favourite
Guest house in Melrose
The Carriage House
5.0 out of 5 average rating, 7 reviews
5.0 (7)
,
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2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
2–7 Nov
2–7 Nov
$1,236 SGD
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for 5 nights
$1,236 SGD for 5 nights
Free cancellation
Top guest favourite
Guest favourite
Rooms in Watertown
Newly Renovated Suite near Boston w/Priv. Bathroom
4.99 out of 5 average rating, 347 reviews
4.99 (347)
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2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
16–21 Aug
16–21 Aug
$1,185 SGD
$1,030 SGD
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for 5 nights
Top guest favourite
Guest favourite
Home in Melrose
Heathman Manor
4.96 out of 5 average rating, 71 reviews
4.96 (71)
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2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
2–7 Aug
2–7 Aug
$2,520 SGD
Show price breakdown
for 5 nights
$2,520 SGD for 5 nights
Free cancellation
Guest favourite
Guest favourite
Home in Lexington
Lexington Battle Green
4.95 out of 5 average rating, 21 reviews
4.95 (21)
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3 bedrooms
3 bedrooms
,
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3 beds
3 beds
,
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3 bathrooms
3 bathrooms
7–12 Aug
7–12 Aug
$3,574 SGD
Show price breakdown
for 5 nights
$3,574 SGD for 5 nights
Guest favourite
Guest favourite
Townhouse in Arlington
Stylish 2BR Near Harvard, MIT & Boston
4.92 out of 5 average rating, 146 reviews
4.92 (146)
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2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
28 Aug – 2 Sept
28 Aug – 2 Sept
$1,763 SGD
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for 5 nights
$1,763 SGD for 5 nights
Free cancellation
Guest favourite
Guest favourite
Flat in Malden
3bed, 1 bath - Near Boston - Free parking
4.9 out of 5 average rating, 129 reviews
4.9 (129)
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2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
17–22 Aug
17–22 Aug
$1,376 SGD
Show price breakdown
for 5 nights
$1,376 SGD for 5 nights
Top guest favourite
Guest favourite
Guest suite in Lexington
Modern Farmhouse Suite in Historic Lexington
4.97 out of 5 average rating, 180 reviews
4.97 (180)
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2 bedrooms
2 bedrooms
,
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3 beds
3 beds
,
·
1 bathroom
1 bathroom
11–16 Aug
11–16 Aug
$2,212 SGD
$1,840 SGD
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for 5 nights
Free cancellation
Guest favourite
Guest favourite
Home in Medford
Queen Anne Victorian in Excellent Location
4.84 out of 5 average rating, 134 reviews
4.84 (134)
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3 bedrooms
3 bedrooms
,
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3 beds
3 beds
,
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2 bathrooms
2 bathrooms
6–11 Aug
6–11 Aug
$3,421 SGD
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for 5 nights
$3,421 SGD for 5 nights
Guest favourite
Guest favourite
Home in Woburn
Large 4Bed 2Bath Clean Alternative to Hotel Living
4.9 out of 5 average rating, 170 reviews
4.9 (170)
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4 bedrooms
4 bedrooms
,
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4 beds
4 beds
,
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2 bathrooms
2 bathrooms
2–7 Aug
2–7 Aug
$2,941 SGD
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for 5 nights
$2,941 SGD for 5 nights
Top guest favourite
Guest favourite
Flat in Melrose
New Cozy 2-bath, 2-bedroom, Boston, airport, Salem
4.96 out of 5 average rating, 95 reviews
4.96 (95)
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2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
2 bathrooms
2 bathrooms
15–20 Nov
15–20 Nov
$1,626 SGD
Show price breakdown
for 5 nights
$1,626 SGD for 5 nights
Free cancellation
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