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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
7–12 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, 63 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 Villa | 4BR + Loft | Sleeps 10
4 bedrooms, 5 beds, 4.5 bathrooms
14–19 Aug
5.0 out of 5 average rating, 3 reviews
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, 248 reviews
Guest favourite
Home in Woburn
Quiet 2BD Single-Family, Parking, No Shared Walls!
2 bedrooms, 2 queen beds, 1 bathroom
9–14 Aug
4.93 out of 5 average rating, 59 reviews
Top guest favourite
Home in Melrose
Heathman Manor
2 bedrooms, 3 beds, 1 bathroom
9–14 Aug
4.96 out of 5 average rating, 73 reviews
Top guest favourite
Home in Stoneham
The Grand Residence
2 bedrooms, 2 queen beds, 1 bathroom
10–15 Nov
4.98 out of 5 average rating, 51 reviews
Guest favourite
Room in Everett
Private Room#3 AC, Free Parking, 5 Miles to Boston
1 bed, 1 bathroom
10–15 Aug
5.0 out of 5 average rating, 7 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
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
Guest favourite
Home in Lexington
Lexington Battle Green
3 bedrooms, 3 beds, 3 bathrooms
7–12 Aug
4.95 out of 5 average rating, 22 reviews
Top guest favourite
Guest suite in Woburn
Private apartment with driveway parking in Woburn
1 bedroom, 1 queen bed, 1 bathroom
9–14 Aug
4.97 out of 5 average rating, 189 reviews
Top guest favourite
Home in Arlington
The Brickhouz at Arlington !
4 bedrooms, 6 beds, 2 bathrooms
25–30 Oct
4.99 out of 5 average rating, 113 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, 121 reviews
Guest favourite
Room in Waltham
Nicely Decorated in Boston Suburb- Yellow Room
1 queen bed, 1 bathroom
23–28 Aug
4.92 out of 5 average rating, 554 reviews
Guest favourite
Home in Melrose
Family-friendly, private, near Boston & Salem, MA
2 bedrooms, 4 beds, 1 bathroom
6–11 Aug
4.82 out of 5 average rating, 17 reviews
Top guest favourite
Guest suite in Arlington
Cozy 1 bed apt Cambridge/Somerville/Arlington line
1 bedroom, 2 beds, 1 bathroom
15–20 Nov
4.93 out of 5 average rating, 227 reviews
Guest favourite
Room in Medford
Queen Bedroom
1 queen bed, 1 bathroom
18–23 Sept
4.97 out of 5 average rating, 34 reviews