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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
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, 4 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
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
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
Room in Arlington
Jo's Celtic Queen in shared apt- parking
1 queen bed, 1 bathroom
20–25 Aug
4.84 out of 5 average rating, 93 reviews
Guest favourite
Room in Arlington
Comfortable room with private access
1 bed, 1.5 bathrooms
15–20 Oct
4.95 out of 5 average rating, 19 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
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
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
Guest favourite
Room in Quincy
Cozy Near Boston, Airport & Beach | Free Parking
1 double bed, 1 bathroom
12–17 Sept
5.0 out of 5 average rating, 6 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
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, 268 reviews
Guest favourite
Guest house in Arlington
300 sqft studio
1 bedroom, 1 bed, 1 bathroom
16–21 Aug
4.81 out of 5 average rating, 175 reviews
Top guest favourite
Flat in Arlington
Sleek & Stylish Condo Retreat, 2BA, W/D
3 bedrooms, 5 beds, 2 bathrooms
30 Aug – 4 Sept
4.87 out of 5 average rating, 55 reviews
Top guest favourite
Room in Arlington
Arlington Craftsman Green Room, Int. Well Restored
1 queen bed, 1 bathroom
26–31 Aug
4.94 out of 5 average rating, 358 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
Room in Arlington
Jo's Sea Queen shared apt-parking
1 bed, 1 bathroom
22–27 Aug
4.85 out of 5 average rating, 20 reviews
Top guest favourite
Rooms in Medford
Quiet Bedroom/Office near Tufts
2 bedrooms, 2 beds, 1.5 bathrooms
16–21 Aug
4.97 out of 5 average rating, 120 reviews