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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
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
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
16–21 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
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
9–14 Aug
4.93 out of 5 average rating, 59 reviews
Top guest favourite
Home in Melrose
Heathman Manor
2 bedrooms, 3 beds
9–14 Aug
4.96 out of 5 average rating, 73 reviews
Guest favourite
Room in Arlington
Comfortable room with private access
1 bed
15–20 Oct
4.94 out of 5 average rating, 18 reviews
Top guest favourite
Guest suite in Woburn
Private apartment with driveway parking in Woburn
1 bedroom, 1 queen bed
9–14 Aug
4.97 out of 5 average rating, 189 reviews
Top guest favourite
Home in Stoneham
The Grand Residence
2 bedrooms, 2 queen beds
10–15 Nov
4.98 out of 5 average rating, 51 reviews
Top guest favourite
Guest suite in Lexington
Modern Farmhouse Suite in Historic Lexington
2 bedrooms, 3 beds
19–24 Aug
4.97 out of 5 average rating, 182 reviews
Top guest favourite
Home in Melrose
Architectural Sanctuary | Sunny Modern Convenient
4 bedrooms, 5 beds
28 Aug – 2 Sept
5.0 out of 5 average rating, 6 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
Top guest favourite
Home in Medford
Bright Family Oasis Near Boston w/ Parking
3 bedrooms, 5 beds
23–28 Aug
4.99 out of 5 average rating, 121 reviews
Guest favourite
Room in Arlington
Jo's Sea Queen shared apt-parking
1 bed
19–24 Aug
4.84 out of 5 average rating, 19 reviews
Top guest favourite
Guest suite in Arlington
Cozy 1 bed apt Cambridge/Somerville/Arlington line
1 bedroom, 2 beds
15–20 Nov
4.93 out of 5 average rating, 227 reviews
Top guest favourite
Bed and breakfast in Belmont
Sweet apt in Belmont 2-family on quiet street
3 bedrooms, 3 beds
7–12 Aug
5.0 out of 5 average rating, 96 reviews
Guest favourite
Room in Waltham
Nicely Decorated in Boston Suburb- Yellow Room
1 queen bed
23–28 Aug
4.92 out of 5 average rating, 554 reviews
Guest favourite
Room in Medford
Queen Bedroom
1 queen bed
18–23 Sept
4.97 out of 5 average rating, 34 reviews