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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
15–20 Aug
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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, 66 reviews
Superhost
Home in Winchester
Luxury Winchester Villa | 4BR + Loft | Sleeps 10
4 bedrooms, 5 beds, 4.5 bathrooms
16–21 Aug
5.0 out of 5 average rating, 4 reviews
Guest favourite
Flat in Woburn
Comfy-Spacious-private 1BR conveniently located
1 bedroom, 2 beds, 1 bathroom
5–10 Sept
4.94 out of 5 average rating, 249 reviews
Guest favourite
Guest suite in Arlington
3 Bedroom 2nd Floor Unit - commute to Boston
3 bedrooms, 3 beds, 1 bathroom
16–21 Aug
4.89 out of 5 average rating, 55 reviews
Top guest favourite
Guest suite in Lexington
Modern Farmhouse Suite in Historic Lexington
2 bedrooms, 3 beds, 1 bathroom
19–24 Aug
4.97 out of 5 average rating, 182 reviews
Top guest favourite
Guest suite in Arlington
Spacious 1-BR apt+parking+laundry. 2nd BR option
1 bedroom, 1 queen bed, 1 bathroom
28 Aug – 2 Sept
4.95 out of 5 average rating, 78 reviews
Guest favourite
Home in Woburn
Quiet 2BD Single-Family, Parking, No Shared Walls!
2 bedrooms, 2 queen beds, 1 bathroom
22–27 Aug
4.93 out of 5 average rating, 61 reviews
Top guest favourite
Guest suite in Stoneham
The Cottage Suite
1 bedroom, 2 beds, 1 bathroom
4–9 Sept
5.0 out of 5 average rating, 36 reviews
Top guest favourite
Guest suite in Arlington
2BR Suite - Bright - Modern - Central AC - Parking
2 bedrooms, 4 beds, 1 bathroom
7–12 Sept
5.0 out of 5 average rating, 168 reviews
Guest favourite
Flat in Lexington
Warm home in Lexington, walk to town, nature trail
2 bedrooms, 2 beds, 1 bathroom
9–14 Sept
4.94 out of 5 average rating, 462 reviews
Guest favourite
Guest house in Arlington
300 sqft studio
1 bedroom, 1 bed, 1 bathroom
16–21 Aug
4.81 out of 5 average rating, 175 reviews
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, 60 reviews
Top guest favourite
Room in Lexington
Spacious bedroom for Family & Women Only
3 beds, 1 bathroom
23–28 Aug
5.0 out of 5 average rating, 79 reviews
Top guest favourite
Flat in Arlington
New Clean 3Br Arlington Heights Condo Walk to Shop
3 bedrooms, 3 beds, 1 bathroom
15–20 Aug
4.95 out of 5 average rating, 95 reviews
Guest favourite
Room in Arlington
Comfortable room with private access
1 bed, 1.5 bathrooms
15–20 Oct
4.95 out of 5 average rating, 19 reviews
Top guest favourite
Flat in Stoneham
Entire guest suite in Stoneham
1 bedroom, 1 queen bed, 1 bathroom
9–14 Nov
4.88 out of 5 average rating, 441 reviews
Top guest favourite
Flat in Stoneham
Cozy Basement Apartment-Stoneham
1 bedroom, 1 queen bed, 1 bathroom
18–23 Aug
4.99 out of 5 average rating, 128 reviews
Top guest favourite
Home in Medford
Bright Family Oasis Near Boston w/ Parking
3 bedrooms, 5 beds, 1.5 bathrooms
23–28 Aug
4.99 out of 5 average rating, 122 reviews