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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
16–21 Aug
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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, 66 reviews
Superhost
Home in Winchester
Luxury Winchester Villa | 4BR + Loft | Sleeps 10
4 bedrooms, 5 beds, 4.5 bathrooms
23–28 Aug
5.0 out of 5 average rating, 4 reviews
Guest favourite
Flat in Woburn
Comfy-Spacious-private 1BR conveniently located
1 bedroom, 2 beds, 1 bathroom
5–10 Sept
4.94 out of 5 average rating, 249 reviews
Guest favourite
Guest suite in Arlington
3 Bedroom 2nd Floor Unit - commute to Boston
3 bedrooms, 3 beds, 1 bathroom
16–21 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
Guest suite in Arlington
Spacious 1-BR apt+parking+laundry. 2nd BR option
1 bedroom, 1 queen bed, 1 bathroom
28 Aug – 2 Sept
4.95 out of 5 average rating, 78 reviews
Top guest favourite
Room in Medford
Free Parking, Private Bath, Only 10min to Boston
1 bed, 2 bathrooms
19–24 Aug
5.0 out of 5 average rating, 57 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, 462 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, 122 reviews
Top guest favourite
Flat in Stoneham
Entire guest suite in Stoneham
1 bedroom, 1 queen bed, 1 bathroom
9–14 Nov
4.88 out of 5 average rating, 441 reviews
Guest favourite
Home in Woburn
Quiet 2BD Single-Family, Parking, No Shared Walls!
2 bedrooms, 2 queen beds, 1 bathroom
22–27 Aug
4.93 out of 5 average rating, 61 reviews
Guest favourite
Room in Medford
Renovated Private Bath | Free Parking, Near Boston
1 queen bed, 1 bathroom
16–21 Aug
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Flat in Somerville
Lovely apt near Boston/Assembly Row/Encore Casino
3 bedrooms, 3 beds, 1 bathroom
8–13 Nov
4.97 out of 5 average rating, 104 reviews
Top guest favourite
Flat in Arlington
Spotless and Modern Apt w/2Ba,W/D,King Bed,Parking
3 bedrooms, 5 beds, 2 bathrooms
6–11 Sept
4.97 out of 5 average rating, 60 reviews
Guest favourite
Room in Arlington
large private room shared bath by T Davis Sq. 闪家@2
1 double bed, 1 bathroom
12–17 Dec
4.95 out of 5 average rating, 170 reviews
Guest favourite
Room in Medford
Queen Bedroom
1 queen bed, 1 bathroom
18–23 Sept
4.97 out of 5 average rating, 34 reviews
Top guest favourite
Rooms in Watertown
Newly Renovated Suite near Boston w/Priv. Bathroom
2 bedrooms, 2 beds, 1 bathroom
8–13 Sept
4.99 out of 5 average rating, 352 reviews
Top guest favourite
Room in Watertown
Private living/dining/ kitchenette - Treetop Suite
1 queen bed, 1 bathroom
23–28 Aug
5.0 out of 5 average rating, 121 reviews