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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, 66 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
16–21 Aug
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Flat in Woburn
Comfy-Spacious-private 1BR conveniently located
1 bedroom, 2 beds, 1 bathroom
16–21 Aug
4.94 out of 5 average rating, 249 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
Guest favourite
Guest suite in Arlington
3 Bedroom 2nd Floor Unit - commute to Boston
3 bedrooms, 3 beds, 1 bathroom
12–17 Aug
4.89 out of 5 average rating, 55 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 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, 60 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
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
Flat in Billerica
Bee-Themed Retreat Near Boston - Unique Stay
1 bedroom, 2 beds, 1 bathroom
27 Sept – 2 Oct
4.99 out of 5 average rating, 215 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, 440 reviews
Top guest favourite
Home in Arlington
The Brickhouz at Arlington !
4 bedrooms, 6 beds, 2 bathrooms
25–30 Oct
4.99 out of 5 average rating, 113 reviews
Top guest favourite
Flat in Arlington
Unique Cathedral Ceiling Condo W/D, Parking
2 bedrooms, 4 beds, 1 bathroom
4–9 Sept
4.96 out of 5 average rating, 101 reviews
Top guest favourite
Guest suite in Woburn
Private apartment with driveway parking in Woburn
1 bedroom, 1 queen bed, 1 bathroom
5–10 Oct
4.97 out of 5 average rating, 189 reviews
Guest favourite
Home in Wakefield
Stylish home next to train to Boston, near Salem
2 bedrooms, 2 queen beds, 2 bathrooms
31 Aug – 5 Sept
5.0 out of 5 average rating, 51 reviews
Guest favourite
Home in Lexington
Lexington Battle Green
3 bedrooms, 3 beds, 3 bathrooms
25–30 Aug
4.96 out of 5 average rating, 23 reviews
Top guest favourite
Guest house in Melrose
Cozy Private Loft, Easy Access to Boston
1 bedroom, 2 beds, 1 bathroom
13–18 Aug
4.96 out of 5 average rating, 57 reviews