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Search results; Over 1,000 homes in Winchester

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Guest suite in Winchester
House on A+ school area w/AC & W/D
2 bedrooms, 4 beds, 1 private bathroom
1–6 Sept
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4.65 out of 5 average rating, 43 reviews
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Guest favourite
Flat in Winchester
Winchester Apartment on Greenway
1 bedroom, 1 bed, 1 bathroom
17–22 Nov
4.96 out of 5 average rating, 68 reviews
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Top guest favourite
Cottage in Winchester
The Little House - a historic New England cottage.
2 bedrooms, 3 beds, 1 bathroom
1–6 Sept
4.95 out of 5 average rating, 86 reviews
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Featured hotel
Room in Burlington
Studio suite - queen - mobility accessible - tub
1 queen bed, 1 bathroom
1–6 Sept
New place to stay
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Guest favourite
Home in Woburn
Stone Cottage with meadow view
3 bedrooms, 3 beds, 2 bathrooms
4–9 Sept
4.95 out of 5 average rating, 184 reviews
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Guest favourite
Flat in Woburn
Comfy-Spacious-private 1BR conveniently located
1 bedroom, 2 beds, 1 bathroom
1–6 Nov
4.94 out of 5 average rating, 252 reviews
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Top guest favourite
Guest suite in Lexington
Modern Farmhouse Suite in Historic Lexington
2 bedrooms, 3 beds, 1 bathroom
3–8 Sept
4.97 out of 5 average rating, 183 reviews
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Guest favourite
Guest suite in Arlington
3 Bedroom 2nd Floor Unit - commute to Boston
3 bedrooms, 3 beds, 1 bathroom
14–19 Sept
4.89 out of 5 average rating, 55 reviews
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Top guest favourite
Home in Woburn
Large 4Bed 2Bath Clean Alternative to Hotel Living
4 bedrooms, 4 queen beds, 2 bathrooms
7–12 Sept
4.9 out of 5 average rating, 174 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, 2 bathrooms
6–11 Sept
4.97 out of 5 average rating, 61 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, 1 bathroom
10–15 Sept
4.95 out of 5 average rating, 78 reviews
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Guest favourite
Home in Woburn
Charming New England Home
5 bedrooms, 6 beds, 3 bathrooms
1–6 Sept
4.93 out of 5 average rating, 58 reviews
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Top guest favourite
Guest suite in Woburn
Private apartment with driveway parking in Woburn
1 bedroom, 1 queen bed, 1 bathroom
5–10 Oct
4.97 out of 5 average rating, 189 reviews
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Top guest favourite
Home in Medford
Bright Family Oasis Near Boston w/ Parking
3 bedrooms, 5 beds, 1.5 bathrooms
3–8 Sept
4.99 out of 5 average rating, 123 reviews
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Guest favourite
Flat in Malden
3bed, 1 bath - Near Boston - Free parking
2 bedrooms, 3 beds, 1 bathroom
4–9 Sept
4.9 out of 5 average rating, 135 reviews
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Top guest favourite
Home in Medford
Queen Anne Victorian in Excellent Location
3 bedrooms, 3 beds, 2 bathrooms
6–11 Sept
4.85 out of 5 average rating, 138 reviews
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Top guest favourite
Home in Melrose
Architectural Sanctuary | Sunny Modern Convenient
4 bedrooms, 5 beds, 1.5 bathrooms
14–19 Sept
5.0 out of 5 average rating, 9 reviews
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Guest favourite
Apartment in Arlington
Spacious Luxury 3 BR, Spotless, W/D, Parking
3 bedrooms, 5 beds, 1 bathroom
6–11 Sept
4.98 out of 5 average rating, 160 reviews
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Top guest favourite
Home in Melrose
Heathman Manor
2 bedrooms, 3 beds, 1 bathroom
1–6 Sept
4.96 out of 5 average rating, 73 reviews