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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
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
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
1–6 Aug
Top guest favourite
Flat in Woburn
Comfy-Spacious-private 1BR conveniently located
1 bedroom, 2 beds
10–15 Aug
4.95 out of 5 average rating, 243 reviews
Guest favourite
Guest suite in Arlington
3 Bedroom 2nd Floor Unit - commute to Boston
3 bedrooms, 3 beds
26–31 Jul
4.88 out of 5 average rating, 52 reviews
Guest favourite
Home in Medford
Charming 3BR/2bath New England Cottage Near Boston
3 bedrooms, 7 beds
20–25 Jul
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Home in Arlington
Lakeview Oasis in Arlington
2 bedrooms, 4 beds
9–14 Aug
4.98 out of 5 average rating, 91 reviews
Top guest favourite
Flat in Stoneham
Cozy Basement Apartment-Stoneham
1 bedroom, 1 queen bed
26–31 Jul
4.99 out of 5 average rating, 126 reviews
Top guest favourite
Guest suite in Arlington
Spacious 1-BR apt+parking+laundry. 2nd BR option
1 bedroom, 1 queen bed
11–16 Aug
4.95 out of 5 average rating, 76 reviews
Guest favourite
Home in Woburn
Large 4Bed 2Bath Clean Alternative to Hotel Living
4 bedrooms, 4 queen beds
26–31 Jul
4.9 out of 5 average rating, 170 reviews
Top guest favourite
Guest suite in Lexington
Modern Farmhouse Suite in Historic Lexington
2 bedrooms, 3 beds
11–16 Aug
4.97 out of 5 average rating, 179 reviews
Top guest favourite
Flat in Arlington
Lakeside apartment, patio, hot tub, outside shower
1 bedroom, 2 beds
30 Aug – 4 Sept
4.98 out of 5 average rating, 215 reviews
Top guest favourite
Guest house in Arlington
300 sqft studio
1 bedroom, 1 bed
8–13 Aug
4.82 out of 5 average rating, 169 reviews
Top guest favourite
Flat in Woburn
Charming 1 BR private entrance apt commuters dream
1 bedroom
10–15 Nov
4.99 out of 5 average rating, 192 reviews
Guest favourite
Guest house in Melrose
The Carriage House
2 bedrooms, 2 beds
2–7 Nov
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Room in Medford
Studio Near Tufts University.
1 queen bed
27 Jul – 1 Aug
5.0 out of 5 average rating, 26 reviews
Top guest favourite
Guest house in Melrose
Spacious& Convenient 1BR unit-20min to Boston
1 bedroom, 2 beds
26–31 Jul
5.0 out of 5 average rating, 26 reviews
Top guest favourite
Flat in Stoneham
Entire guest suite in Stoneham
1 bedroom, 1 queen bed
23–28 Aug
4.88 out of 5 average rating, 432 reviews