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Search results; Over 1,000 homes in Winchester

Guest suite in Winchester
House on A+ school area w/AC & W/D
2 bedrooms, 4 beds, 1 private bathroom
14–19 Sept
,
4.65 out of 5 average rating, 43 reviews
Top guest favourite
Cottage in Winchester
The Little House - a historic New England cottage.
2 bedrooms, 3 beds, 1 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
17–22 Nov
4.96 out of 5 average rating, 68 reviews
Top guest favourite
Room in Lexington
Spacious bedroom for Family & Women Only
3 beds, 1 bathroom
1–6 Sept
5.0 out of 5 average rating, 79 reviews
Guest favourite
Room in Medford
Queen Bedroom
1 queen bed, 1 bathroom
28 Sept – 3 Oct
4.97 out of 5 average rating, 34 reviews
Top guest favourite
Guest suite in Arlington
Charming 1Bd Apt. in Historic Arlington Home
1 bedroom, 1 queen bed, 1.5 bathrooms
9–14 Nov
4.96 out of 5 average rating, 70 reviews
Top guest favourite
Guest suite in Medford
Beautiful 1 Bedroom, 1 Bathroom in Medford
1 bedroom, 1 queen bed, 1 bathroom
13–18 Sept
4.9 out of 5 average rating, 269 reviews
Guest favourite
Guest house in Melrose
The Carriage House
2 bedrooms, 2 beds, 1 bathroom
9–14 Nov
5.0 out of 5 average rating, 9 reviews
Top guest favourite
Guest suite in Lexington
Modern Farmhouse Suite in Historic Lexington
2 bedrooms, 3 beds, 1 bathroom
3–8 Sept
4.97 out of 5 average rating, 183 reviews
Guest favourite
Flat in Woburn
Comfy-Spacious-private 1BR conveniently located
1 bedroom, 2 beds, 1 bathroom
8–13 Sept
4.94 out of 5 average rating, 251 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, 53 reviews
Flat in Belmont
Lovely 3 bed 2 bath, minutes to Boston / Cambridge
3 bedrooms, 4 beds, 2 bathrooms
1–6 Sept
New place to stay
Top guest favourite
Guest suite in Stoneham
The Cottage Suite
1 bedroom, 2 beds, 1 bathroom
5–10 Nov
5.0 out of 5 average rating, 36 reviews
Top guest favourite
Home in Melrose
Heathman Manor
2 bedrooms, 3 beds, 1 bathroom
1–6 Sept
4.96 out of 5 average rating, 73 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, 228 reviews
Guest favourite
Home in Woburn
Quiet 2BD Single-Family, Parking, No Shared Walls!
2 bedrooms, 2 queen beds, 1 bathroom
1–6 Sept
4.94 out of 5 average rating, 63 reviews
Guest favourite
Home in Woburn
Stone Cottage with meadow view
3 bedrooms, 3 beds, 2 bathrooms
4–9 Sept
4.95 out of 5 average rating, 184 reviews
Top guest favourite
Room in Medford
Studio Near Tufts University.
1 queen bed, 1 bathroom
1–6 Sept
5.0 out of 5 average rating, 27 reviews
Top guest favourite
Home in Medford
Queen Anne Victorian in Excellent Location
3 bedrooms, 3 beds, 2 bathrooms
6–11 Sept
4.85 out of 5 average rating, 138 reviews