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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, 63 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, 3 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
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
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 Melrose
Heathman Manor
2 bedrooms, 3 beds, 1 bathroom
13–18 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
Flat in Reading
Luxury 1BR Apt, Next to Commuter Rail #2009
1 bedroom, 1 bathroom
9–14 Aug
4.88 out of 5 average rating, 26 reviews
Guest favourite
Room in Arlington
Jo's Sea Queen shared apt-parking
1 bed, 1 bathroom
19–24 Aug
4.84 out of 5 average rating, 19 reviews
Guest favourite
Guest suite in Arlington
3 Bedroom 2nd Floor Unit - commute to Boston
3 bedrooms, 3 beds, 1 bathroom
11–16 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
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
Guest favourite
Home in Lexington
Lexington Battle Green
3 bedrooms, 3 beds, 3 bathrooms
8–13 Aug
4.95 out of 5 average rating, 22 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
Top guest favourite
Home in Melrose
Architectural Sanctuary | Sunny Modern Convenient
4 bedrooms, 5 beds, 1.5 bathrooms
28 Aug – 2 Sept
5.0 out of 5 average rating, 7 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
Top guest favourite
Bed and breakfast in Belmont
Sweet apt in Belmont 2-family on quiet street
3 bedrooms, 3 beds, 1 bathroom
8–13 Aug
5.0 out of 5 average rating, 96 reviews