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Search results; Over 1,000 homes in Winchester

Top guest favourite
Cottage in Winchester
The Little House - a historic New England cottage.
2 bedrooms, 3 beds, 1 private bathroom
1–6 Sept
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4.95 out of 5 average rating, 86 reviews
Guest favourite
Flat in Winchester
Winchester Apartment on Greenway
4.95 out of 5 average rating, 60 reviews, 1 bedroom, 1 bed, 1 bathroom
10–15 Nov
Guest favourite
Home in Winchester
3 Bedroom Boston-area Gem
4.96 out of 5 average rating, 27 reviews, 3 bedrooms, 4 beds, 1 bathroom
14–19 Aug
Superhost
Home in Winchester
Luxury Winchester Estate | 4BR + Loft | Sleeps 10
4 bedrooms, 5 beds, 4.5 bathrooms
1–6 Aug
Top guest favourite
Flat in Woburn
Comfy-Spacious-private 1BR conveniently located
4.95 out of 5 average rating, 244 reviews, 1 bedroom, 2 beds, 1 bathroom
10–15 Aug
Top guest favourite
Rooms in Watertown
Newly Renovated Suite near Boston w/Priv. Bathroom
4.99 out of 5 average rating, 347 reviews, 2 bedrooms, 2 beds, 1 bathroom
16–21 Aug
Guest favourite
Guest suite in Arlington
3 Bedroom 2nd Floor Unit - commute to Boston
4.88 out of 5 average rating, 52 reviews, 3 bedrooms, 3 beds, 1 bathroom
6–11 Aug
Superhost
Home in Melrose
Architectural Sanctuary | Sunny Modern Convenient
5.0 out of 5 average rating, 3 reviews, 4 bedrooms, 5 beds, 1.5 bathrooms
6–11 Aug
Guest favourite
Room in Arlington
Jo's Sea Queen shared apt-parking
4.83 out of 5 average rating, 18 reviews, 1 bed, 1 bathroom
10–15 Aug
Guest favourite
Townhouse in Arlington
Stylish 2BR Near Harvard, MIT & Boston
4.92 out of 5 average rating, 146 reviews, 2 bedrooms, 2 beds, 1 bathroom
28 Aug – 2 Sept
Guest favourite
Guest house in Melrose
The Carriage House
5.0 out of 5 average rating, 7 reviews, 2 bedrooms, 2 beds, 1 bathroom
2–7 Nov
Top guest favourite
Home in Medford
Bright Family Oasis Near Boston w/ Parking
4.99 out of 5 average rating, 119 reviews, 3 bedrooms, 5 beds, 1.5 bathrooms
12–17 Aug
Top guest favourite
Home in Melrose
Heathman Manor
4.96 out of 5 average rating, 71 reviews, 2 bedrooms, 3 beds, 1 bathroom
2–7 Aug
Top guest favourite
Home in Arlington
Spacious single family house w/ parking
5.0 out of 5 average rating, 11 reviews, 4 bedrooms, 4 beds, 2.5 bathrooms
1–6 Aug
Top guest favourite
Guest house in Arlington
300 sqft studio
4.82 out of 5 average rating, 169 reviews, 1 bedroom, 1 bed, 1 bathroom
13–18 Aug
Top guest favourite
Flat in Melrose
New Cozy 2-bath, 2-bedroom, Boston, airport, Salem
4.96 out of 5 average rating, 95 reviews, 2 bedrooms, 2 beds, 2 bathrooms
15–20 Nov
Top guest favourite
Flat in Woburn
Charming 1 BR private entrance apt commuters dream
4.99 out of 5 average rating, 192 reviews, 1 bedroom, 1 bathroom
10–15 Nov
Top guest favourite
Flat in Arlington
Unique Cathedral Ceiling Condo W/D, Parking
4.96 out of 5 average rating, 101 reviews, 2 bedrooms, 4 beds, 1 bathroom
18–23 Aug
Top guest favourite
Flat in Cambridge
Spacious 2bd/1ba Apt | Free Parking
4.99 out of 5 average rating, 102 reviews, 2 bedrooms, 3 beds, 1 bathroom
6–11 Sept