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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
12–17 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
Top guest favourite
Guest suite in Arlington
Charming 1Bd Apt. in Historic Arlington Home
1 bedroom, 1 queen bed, 1.5 bathrooms
9–14 Nov
4.96 out of 5 average rating, 70 reviews
Top guest favourite
Home in Stoneham
The Grand Residence
2 bedrooms, 2 queen beds, 1 bathroom
17–22 Nov
4.98 out of 5 average rating, 54 reviews
Guest favourite
Guest house in Melrose
The Carriage House
2 bedrooms, 2 beds, 1 bathroom
28 Nov – 3 Dec
5.0 out of 5 average rating, 10 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
Guest suite in Arlington
Cozy 1 bed apt Cambridge/Somerville/Arlington line
1 bedroom, 2 beds, 1 bathroom
16–21 Nov
4.93 out of 5 average rating, 230 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
Top guest favourite
Flat in Arlington
Spotless and Modern Apt w/2Ba,W/D,King Bed,Parking
3 bedrooms, 5 beds, 2 bathrooms
25–30 Oct
4.97 out of 5 average rating, 64 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
Flat in Medford
Garden Apartment for Vacation & Business Travelers
1 bedroom, 2 beds, 1 bathroom
1–6 Nov
4.93 out of 5 average rating, 395 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
Top guest favourite
Flat in Woburn
Sofima-Cozy and Charming 2-bedroom apartment.
2 bedrooms, 2 beds, 1 bathroom
4–9 Nov
4.98 out of 5 average rating, 41 reviews
Top guest favourite
Home in Stoneham
Stunning 5BR, 4BA | Theater, Gym, Game Room & more
5 bedrooms, 5 beds, 4 bathrooms
14–19 Sept
5.0 out of 5 average rating, 8 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 Stoneham
The Cottage Suite
1 bedroom, 2 beds, 1 bathroom
5–10 Nov
5.0 out of 5 average rating, 37 reviews
Featured hotel
Room in Burlington
Studio suite - queen - mobility accessible - tub
1 queen bed, 1 bathroom
26 Sept – 1 Oct
Top guest favourite
Home in Medford
Queen Anne Victorian in Excellent Location
3 bedrooms, 3 beds, 2 bathrooms
13–18 Sept
4.85 out of 5 average rating, 139 reviews