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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
1 bedroom, 1 bed, 1 bathroom
10–15 Nov
4.95 out of 5 average rating, 60 reviews
Guest favourite
Home in Winchester
3 Bedroom Boston-area Gem
3 bedrooms, 4 beds, 1 bathroom
14–19 Aug
4.96 out of 5 average rating, 27 reviews
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
1 bedroom, 2 beds, 1 bathroom
10–15 Aug
4.95 out of 5 average rating, 245 reviews
Guest favourite
Guest suite in Arlington
3 Bedroom 2nd Floor Unit - commute to Boston
3 bedrooms, 3 beds, 1 bathroom
6–11 Aug
4.88 out of 5 average rating, 52 reviews
Superhost
Home in Melrose
Architectural Sanctuary | Sunny Modern Convenient
4 bedrooms, 5 beds, 1.5 bathrooms
6–11 Aug
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Medford
Bright Family Oasis Near Boston w/ Parking
3 bedrooms, 5 beds, 1.5 bathrooms
12–17 Aug
4.99 out of 5 average rating, 119 reviews
Top guest favourite
Home in Melrose
Heathman Manor
2 bedrooms, 3 beds, 1 bathroom
2–7 Aug
4.96 out of 5 average rating, 71 reviews
Guest favourite
Townhouse in Arlington
Stylish 2BR Near Harvard, MIT & Boston
2 bedrooms, 2 beds, 1 bathroom
28 Aug – 2 Sept
4.92 out of 5 average rating, 146 reviews
Guest favourite
Home in Lexington
Lexington Battle Green
3 bedrooms, 3 beds, 3 bathrooms
7–12 Aug
4.95 out of 5 average rating, 21 reviews
Guest favourite
Guest house in Melrose
The Carriage House
2 bedrooms, 2 beds, 1 bathroom
2–7 Nov
5.0 out of 5 average rating, 7 reviews
Guest favourite
Home in Woburn
Quiet 2BD Single-Family, Parking, No Shared Walls!
2 bedrooms, 2 queen beds, 1 bathroom
1–6 Aug
4.95 out of 5 average rating, 57 reviews
Top guest favourite
Guest suite in Lexington
Modern Farmhouse Suite in Historic Lexington
2 bedrooms, 3 beds, 1 bathroom
11–16 Aug
4.97 out of 5 average rating, 181 reviews
Top guest favourite
Flat in Arlington
Unique Cathedral Ceiling Condo W/D, Parking
2 bedrooms, 4 beds, 1 bathroom
18–23 Aug
4.96 out of 5 average rating, 101 reviews
Home in Somerville
Newly Renovated• Free Parking • Deck • 5 Min to T
3 bedrooms, 3 beds, 2 bathrooms
23–28 Aug
New place to stay
Top guest favourite
Home in Arlington
Lakeview Oasis in Arlington
2 bedrooms, 4 beds, 1 bathroom
9–14 Aug
4.98 out of 5 average rating, 91 reviews
Top guest favourite
Flat in Woburn
Charming 1 BR private entrance apt commuters dream
1 bedroom, 1 bathroom
10–15 Nov
4.99 out of 5 average rating, 192 reviews
Top guest favourite
Flat in Melrose
New Cozy 2-bath, 2-bedroom, Boston, airport, Salem
2 bedrooms, 2 queen beds, 2 bathrooms
15–20 Nov
4.96 out of 5 average rating, 95 reviews