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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
11–16 Sept
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4.95 out of 5 average rating, 87 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, 71 reviews
Guest favourite
Room in Winchester
Private Suite with Full Bath & Separate Entrance
1 king bed, 1 bathroom
13–20 Oct
5.0 out of 5 average rating, 7 reviews
Guest favourite
Home in Woburn
Stone Cottage with meadow view
3 bedrooms, 3 beds, 2 bathrooms
25–30 Oct
4.95 out of 5 average rating, 186 reviews
Top guest favourite
Guest suite in Arlington
Spacious 1-BR apt+parking+laundry. 2nd BR option
1 bedroom, 1 queen bed, 1 bathroom
2–7 Nov
4.95 out of 5 average rating, 79 reviews
Guest favourite
Flat in Woburn
Comfy-Spacious-private 1BR conveniently located
1 bedroom, 2 beds, 1 bathroom
5–10 Nov
4.94 out of 5 average rating, 254 reviews
Guest favourite
Guest suite in Arlington
3 Bedroom 2nd Floor Unit - commute to Boston
3 bedrooms, 3 beds, 1 bathroom
11–16 Sept
4.89 out of 5 average rating, 56 reviews
Top guest favourite
Guest suite in Lexington
Modern Farmhouse Suite in Historic Lexington
2 bedrooms, 3 beds, 1 bathroom
13–18 Sept
4.97 out of 5 average rating, 185 reviews
Top guest favourite
Room in Lexington
Spacious bedroom for Family & Women Only
3 beds, 1 bathroom
23–28 Oct
5.0 out of 5 average rating, 79 reviews
Top guest favourite
Home in Lexington
Lexington Battle Green
3 bedrooms, 3 beds, 3 bathrooms
12–17 Sept
4.96 out of 5 average rating, 25 reviews
Top guest favourite
Flat in Arlington
New Clean 3Br Arlington Heights Condo Walk to Shop
3 bedrooms, 3 beds, 1 bathroom
31 Oct – 5 Nov
4.95 out of 5 average rating, 97 reviews
Top guest favourite
Home in Woburn
Large 4Bed 2Bath Clean Alternative to Hotel Living
4 bedrooms, 4 queen beds, 2 bathrooms
14–19 Sept
4.9 out of 5 average rating, 174 reviews
Top guest favourite
Home in Melrose
Heathman Manor
2 bedrooms, 3 beds, 1 bathroom
4–9 Nov
4.96 out of 5 average rating, 73 reviews
Top guest favourite
Guest suite in Woburn
Private apartment with driveway parking in Woburn
1 bedroom, 1 queen bed, 1 bathroom
20–25 Oct
4.97 out of 5 average rating, 192 reviews
Top guest favourite
Flat in Arlington
Cheerful 1-bedroom home with free parking
1 bedroom, 1 queen bed, 1 bathroom
20–25 Sept
4.98 out of 5 average rating, 80 reviews
Top guest favourite
Home in Medford
Queen Anne Victorian in Excellent Location
3 bedrooms, 3 beds, 2 bathrooms
12–17 Sept
4.85 out of 5 average rating, 139 reviews
Top guest favourite
Home in Stoneham
Quiet Boston-Area Sanctuary, Elegant & Comfortable
5 bedrooms, 6 beds, 3.5 bathrooms
24–29 Oct
4.97 out of 5 average rating, 35 reviews
Flat in Arlington
Spacious Luxury Two-Level Home in East Arlington
4 bedrooms, 4 beds, 3 bathrooms
11–16 Sept
New place to stay
Guest favourite
Home in Woburn
Quiet 2BD Single-Family, Parking, No Shared Walls!
2 bedrooms, 2 queen beds, 1 bathroom
27 Sept – 2 Oct
4.94 out of 5 average rating, 66 reviews