filters

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
,
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, 62 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
Guest favourite
Place to stay in Lexington
Boston Lexington Suite Queen Bed Private Full Bath
1 bedroom, 2 beds, 1.5 bathrooms
3–8 Aug
4.86 out of 5 average rating, 49 reviews
Guest favourite
Guest suite in Arlington
3 Bedroom 2nd Floor Unit - commute to Boston
3 bedrooms, 3 beds, 1 bathroom
6–11 Aug
4.89 out of 5 average rating, 54 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
Room in Arlington
Arlington Craftsman Blue Room, Int. Well Restored
1 queen bed, 1 bathroom
14–19 Aug
4.98 out of 5 average rating, 374 reviews
Guest favourite
Room in Arlington
Jo's Celtic Queen in shared apt- parking
1 queen bed, 1 bathroom
17–22 Aug
4.84 out of 5 average rating, 92 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
Top guest favourite
Home in Woburn
Large 4Bed 2Bath Clean Alternative to Hotel Living
4 bedrooms, 4 queen beds, 2 bathrooms
9–14 Aug
4.9 out of 5 average rating, 173 reviews
Guest favourite
Home in Wakefield
Stylish home next to train to Boston, near Salem
2 bedrooms, 2 queen beds, 2 bathrooms
7–12 Aug
5.0 out of 5 average rating, 49 reviews
Top guest favourite
Room in Medford
Studio Near Tufts University.
1 queen bed, 1 bathroom
13–18 Aug
5.0 out of 5 average rating, 26 reviews
Top guest favourite
Home in Arlington
Lakeview Oasis in Arlington
2 bedrooms, 4 beds, 1 bathroom
9–14 Aug
4.98 out of 5 average rating, 92 reviews
Top guest favourite
Guest suite in Arlington
Cozy 1 bed apt Cambridge/Somerville/Arlington line
1 bedroom, 2 beds, 1 bathroom
19–24 Sept
4.93 out of 5 average rating, 226 reviews
Guest favourite
Room in Everett
Private Room#3 AC, Free Parking, 5 Miles to Boston
1 bed, 1 bathroom
8–13 Aug
5.0 out of 5 average rating, 7 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
Flat in Stoneham
Entire guest suite in Stoneham
1 bedroom, 1 queen bed, 1 bathroom
3–8 Nov
4.88 out of 5 average rating, 438 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, 461 reviews