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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
10–15 Nov
4.95 out of 5 average rating, 62 reviews
Guest favourite
Home in Winchester
3 Bedroom Boston-area Gem
3 bedrooms, 4 beds
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
1–6 Aug
Guest favourite
Home in Woburn
Quiet 2BD Single-Family, Parking, No Shared Walls!
2 bedrooms, 2 queen beds
9–14 Aug
4.95 out of 5 average rating, 57 reviews
Top guest favourite
Flat in Woburn
Comfy-Spacious-private 1BR conveniently located
1 bedroom, 2 beds
10–15 Aug
4.95 out of 5 average rating, 247 reviews
Guest favourite
Guest suite in Arlington
3 Bedroom 2nd Floor Unit - commute to Boston
3 bedrooms, 3 beds
6–11 Aug
4.89 out of 5 average rating, 53 reviews
Top guest favourite
Guest suite in Lexington
Modern Farmhouse Suite in Historic Lexington
2 bedrooms, 3 beds
11–16 Aug
4.97 out of 5 average rating, 181 reviews
Top guest favourite
Home in Woburn
Large 4Bed 2Bath Clean Alternative to Hotel Living
4 bedrooms, 4 queen beds
9–14 Aug
4.9 out of 5 average rating, 173 reviews
Guest favourite
Room in Arlington
Jo's Sea Queen shared apt-parking
1 bed
19–24 Aug
4.83 out of 5 average rating, 18 reviews
Top guest favourite
Flat in Woburn
Sofima-Cozy and Charming 2-bedroom apartment.
2 bedrooms, 2 beds
3–8 Sept
4.97 out of 5 average rating, 38 reviews
Top guest favourite
Home in Melrose
Heathman Manor
2 bedrooms, 3 beds
2–7 Aug
4.96 out of 5 average rating, 73 reviews
Top guest favourite
Home in Arlington
Lakeview Oasis in Arlington
2 bedrooms, 4 beds
9–14 Aug
4.98 out of 5 average rating, 92 reviews
Top guest favourite
Room in Medford
Free Parking, Private Bath, Only 10min to Boston
1 bed
12–17 Aug
5.0 out of 5 average rating, 55 reviews
Top guest favourite
Guest suite in Arlington
2BR Suite - Bright - Modern - Central AC - Parking
2 bedrooms, 4 beds
7–12 Sept
5.0 out of 5 average rating, 168 reviews
Guest favourite
Townhouse in Arlington
Stylish 2BR Near Harvard, MIT & Boston
2 bedrooms, 2 beds
31 Aug – 5 Sept
4.93 out of 5 average rating, 147 reviews
Top guest favourite
Room in Medford
Studio Near Tufts University.
1 queen bed
13–18 Aug
5.0 out of 5 average rating, 26 reviews
Top guest favourite
Guest suite in Woburn
Private apartment with driveway parking in Woburn
1 bedroom, 1 queen bed
9–14 Aug
4.97 out of 5 average rating, 188 reviews
Guest favourite
Home in Cambridge
Cambridge Cottage Retreat Near Harvard
1 bedroom, 2 beds
11–16 Aug
5.0 out of 5 average rating, 5 reviews