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Search results; Over 1,000 homes in Winchester

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Superhost
Room in Winchester
Spirit room for a stay
1 bedroom, 1 bed, 1 bathroom
20–25 Sept
,
4.71 out of 5 average rating, 31 reviews
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Top guest favourite
Cottage in Winchester
The Little House - a historic New England cottage.
2 bedrooms, 3 beds
4–9 Sept
4.95 out of 5 average rating, 86 reviews
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Top guest favourite
Flat in Winchester
Winchester Apartment on Greenway
1 bedroom, 1 bed
17–22 Nov
4.96 out of 5 average rating, 69 reviews
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Guest favourite
Home in Woburn
Stone Cottage with meadow view
3 bedrooms, 3 beds
25–30 Oct
4.95 out of 5 average rating, 185 reviews
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Top guest favourite
Flat in Arlington
Spotless and Modern Apt w/2Ba,W/D,King Bed,Parking
3 bedrooms, 5 beds
6–11 Sept
4.97 out of 5 average rating, 61 reviews
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Top guest favourite
Home in Medford
Queen Anne Victorian in Excellent Location
3 bedrooms, 3 beds
6–11 Sept
4.85 out of 5 average rating, 139 reviews
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Guest favourite
Home in Woburn
Charming New England Home
5 bedrooms, 6 beds
20–25 Sept
4.93 out of 5 average rating, 59 reviews
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Guest favourite
Home in Lexington
Lexington Battle Green
3 bedrooms, 3 beds
12–17 Sept
4.96 out of 5 average rating, 24 reviews
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Top guest favourite
Guest suite in Lexington
Modern Farmhouse Suite in Historic Lexington
2 bedrooms, 3 beds
3–8 Sept
4.97 out of 5 average rating, 183 reviews
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Guest favourite
Flat in Woburn
Comfy-Spacious-private 1BR conveniently located
1 bedroom, 2 beds
11–16 Sept
4.94 out of 5 average rating, 253 reviews
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Top guest favourite
Home in Woburn
Large 4Bed 2Bath Clean Alternative to Hotel Living
4 bedrooms, 4 queen beds
14–19 Sept
4.9 out of 5 average rating, 174 reviews
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Guest favourite
Rooms in Burlington
| 2 BR Suite w Kitchen| Free Breakfast- Sleeps 7
2 bedrooms, 4 beds
6–11 Sept
4.9 out of 5 average rating, 21 reviews
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Top guest favourite
Guest suite in Arlington
Spacious 1-BR apt+parking+laundry. 2nd BR option
1 bedroom, 1 queen bed
10–15 Sept
4.95 out of 5 average rating, 79 reviews
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Guest favourite
Guest suite in Arlington
3 Bedroom 2nd Floor Unit - commute to Boston
3 bedrooms, 3 beds
20–25 Sept
4.89 out of 5 average rating, 55 reviews
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Top guest favourite
Home in Melrose
Heathman Manor
2 bedrooms, 3 beds
3–8 Sept
4.96 out of 5 average rating, 73 reviews
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Top guest favourite
Home in Medford
Bright Family Oasis Near Boston w/ Parking
3 bedrooms, 5 beds
3–8 Oct
4.99 out of 5 average rating, 123 reviews
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Top guest favourite
Guest suite in Arlington
2BR Suite - Bright - Modern - Central AC - Parking
2 bedrooms, 4 beds
7–12 Sept
5.0 out of 5 average rating, 170 reviews
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Top guest favourite
Flat in Arlington
New Clean 3Br Arlington Heights Condo Walk to Shop
3 bedrooms, 3 beds
8–13 Sept
4.95 out of 5 average rating, 97 reviews
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Top guest favourite
Home in Medford
Hot tub - Arcade - Boston themed rooms
6 bedrooms, 13 beds
13–18 Sept
5.0 out of 5 average rating, 15 reviews