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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
Featured hotel
Room in Burlington
Studio suite - queen - mobility accessible - tub
1 queen bed, 1 bathroom
26 Sept – 1 Oct
Featured hotel
Room in Cambridge
Queen ADA, patio
1 queen bed, 1 bathroom
6–11 Dec
5.0 out of 5 average rating, 6 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
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
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
Home in Lexington
Lexington Battle Green
3 bedrooms, 3 beds, 3 bathrooms
13–18 Sept
4.96 out of 5 average rating, 25 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 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, 124 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
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
Top guest favourite
Home in Melrose
Heathman Manor
2 bedrooms, 3 beds, 1 bathroom
4–9 Nov
4.96 out of 5 average rating, 73 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
Guest suite in Arlington
2BR Suite - Bright - Modern - Central AC - Parking
2 bedrooms, 4 beds, 1 bathroom
26–31 Oct
5.0 out of 5 average rating, 170 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
Top guest favourite
Flat in Melrose
New Cozy 2-bath, 2-bedroom, Boston, airport, Salem
2 bedrooms, 2 queen beds, 2 bathrooms
15–20 Nov
4.96 out of 5 average rating, 102 reviews