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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, 1 bathroom
10–15 Nov
4.95 out of 5 average rating, 63 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, 3 reviews
Guest favourite
Home in Winchester
3 Bedroom Boston-area Gem
3 bedrooms, 4 beds, 1 bathroom
14–19 Aug
4.96 out of 5 average rating, 27 reviews
Top guest favourite
Flat in Woburn
Comfy-Spacious-private 1BR conveniently located
1 bedroom, 2 beds, 1 bathroom
10–15 Aug
4.95 out of 5 average rating, 248 reviews
Guest favourite
Home in Woburn
Quiet 2BD Single-Family, Parking, No Shared Walls!
2 bedrooms, 2 queen beds, 1 bathroom
9–14 Aug
4.93 out of 5 average rating, 59 reviews
Guest favourite
Room in Arlington
Jo's Sea Queen shared apt-parking
1 bed, 1 bathroom
19–24 Aug
4.84 out of 5 average rating, 19 reviews
Top guest favourite
Flat in Woburn
Sofima-Cozy and Charming 2-bedroom apartment.
2 bedrooms, 2 beds, 1 bathroom
4–9 Nov
4.97 out of 5 average rating, 38 reviews
Top guest favourite
Guest suite in Arlington
2BR Suite - Bright - Modern - Central AC - Parking
2 bedrooms, 4 beds, 1 bathroom
7–12 Sept
5.0 out of 5 average rating, 168 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, 77 reviews
Guest favourite
Guest suite in Arlington
3 Bedroom 2nd Floor Unit - commute to Boston
3 bedrooms, 3 beds, 1 bathroom
11–16 Aug
4.89 out of 5 average rating, 55 reviews
Top guest favourite
Guest suite in Woburn
Private apartment with driveway parking in Woburn
1 bedroom, 1 queen bed, 1 bathroom
9–14 Aug
4.97 out of 5 average rating, 189 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, 54 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
Room in Quincy
Cozy Private Room • Walk to Beach • Free Parking
1 double bed, 1 bathroom
24–29 Aug
5.0 out of 5 average rating, 3 reviews
Guest favourite
Rooms in Burlington
| 2 BR Suite w Kitchen| Free Breakfast- Sleeps 7
2 bedrooms, 4 beds, 2 bathrooms
24–29 Aug
4.88 out of 5 average rating, 17 reviews
Top guest favourite
Flat in Medford
Garden Apartment for Vacation & Business Travelers
1 bedroom, 2 beds, 1 bathroom
23–28 Aug
4.93 out of 5 average rating, 393 reviews
Top guest favourite
Home in Woburn
Large 4Bed 2Bath Clean Alternative to Hotel Living
4 bedrooms, 4 queen beds, 2 bathrooms
7–12 Sept
4.9 out of 5 average rating, 173 reviews
Guest favourite
Home in Cambridge
Cambridge Cottage Retreat Near Harvard
1 bedroom, 2 beds, 1 bathroom
11–16 Aug
5.0 out of 5 average rating, 5 reviews