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Search results; Over 1,000 homes in Winchester

Guest favourite
Flat in Winchester
Winchester Apartment on Greenway
1 bedroom, 1 bed, 1 private bathroom
17–22 Nov
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4.96 out of 5 average rating, 71 reviews
Top guest favourite
Cottage in Winchester
The Little House - a historic New England cottage.
2 bedrooms, 3 beds, 1 bathroom
15–20 Sept
4.95 out of 5 average rating, 87 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, 187 reviews
Top guest favourite
Home in Woburn
Large 4Bed 2Bath Clean Alternative to Hotel Living
4 bedrooms, 4 queen beds, 2 bathrooms
20–25 Sept
4.9 out of 5 average rating, 174 reviews
Guest favourite
Guest suite in Arlington
3 Bedroom 2nd Floor Unit - commute to Boston
3 bedrooms, 3 beds, 1 bathroom
20–25 Sept
4.89 out of 5 average rating, 56 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 Medford
Hot tub - Arcade - Boston themed rooms
6 bedrooms, 13 beds, 3 bathrooms
18–23 Sept
5.0 out of 5 average rating, 16 reviews
Top guest favourite
Home in Melrose
Architectural Sanctuary | Sunny Modern Convenient
4 bedrooms, 5 beds, 1.5 bathrooms
20–25 Sept
5.0 out of 5 average rating, 11 reviews
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, 67 reviews
Top guest favourite
Home in Medford
Bright Family Oasis Near Boston w/ Parking
3 bedrooms, 5 beds, 1.5 bathrooms
3–8 Oct
4.99 out of 5 average rating, 125 reviews
Top guest favourite
Home in Lexington
Lexington Battle Green
3 bedrooms, 3 beds, 3 bathrooms
16–21 Sept
4.96 out of 5 average rating, 25 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
Top guest favourite
Home in Medford
Queen Anne Victorian in Excellent Location
3 bedrooms, 3 beds, 2 bathrooms
16–21 Sept
4.85 out of 5 average rating, 139 reviews
Top guest favourite
Guest suite in Lexington
Modern Farmhouse Suite in Historic Lexington
2 bedrooms, 3 beds, 1 bathroom
29 Sept – 4 Oct
4.97 out of 5 average rating, 187 reviews
Superhost
Rooms in Arlington
Sunny Quiet 2-3 Bedroom Apt-Parking&Pets
3 bedrooms, 3 beds, 1 bathroom
1–6 Nov
Guest favourite
Home in Woburn
Charming New England Home
5 bedrooms, 6 beds, 3 bathrooms
24–29 Oct
4.93 out of 5 average rating, 60 reviews
Top guest favourite
Flat in Arlington
Sleek & Stylish Condo Retreat, 2BA, W/D
3 bedrooms, 5 beds, 2 bathrooms
19–24 Sept
4.88 out of 5 average rating, 60 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