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Search results; Over 1,000 homes in Winchester

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Top guest favourite
Cottage in Winchester
The Little House - a historic New England cottage.
2 bedrooms, 3 beds, 1 private bathroom
18–23 Sept
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4.95 out of 5 average rating, 87 reviews
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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
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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
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Top 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, 188 reviews
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Guest suite in Woburn
Private apartment with driveway parking in Woburn
1 bedroom, 1 queen bed, 1 bathroom
26 Sept – 1 Oct
4.97 out of 5 average rating, 192 reviews
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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
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Home in Lexington
Lexington Battle Green
3 bedrooms, 3 beds, 3 bathrooms
19–24 Sept
4.96 out of 5 average rating, 25 reviews
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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
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Top guest favourite
Flat in Woburn
Comfy-Spacious-private 1BR conveniently located
1 bedroom, 2 beds, 1 bathroom
5–10 Nov
4.95 out of 5 average rating, 255 reviews
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Guest suite in Arlington
Spacious 1-BR apt+parking+laundry. 2nd BR option
1 bedroom, 1 queen bed, 1 bathroom
2–7 Nov
4.95 out of 5 average rating, 79 reviews
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Home in Somerville
6BR2Bath LUXE HOME
6 bedrooms, 8 beds, 2 bathrooms
20–25 Sept
5.0 out of 5 average rating, 23 reviews
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Room in Medford
Studio Near Tufts University.
1 queen bed, 1 bathroom
20–25 Oct
5.0 out of 5 average rating, 27 reviews
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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
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Home in Medford
Queen Anne Victorian in Excellent Location
3 bedrooms, 3 beds, 2 bathrooms
19–24 Sept
4.85 out of 5 average rating, 139 reviews
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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
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Flat in Somerville
Lovely apt near Boston/Assembly Row/Encore Casino
3 bedrooms, 3 beds, 1 bathroom
8–13 Nov
4.97 out of 5 average rating, 112 reviews
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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, 126 reviews
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Top guest favourite
Apartment in Arlington
Spacious Luxury 3 BR, Spotless, W/D, Parking
3 bedrooms, 5 beds, 1 bathroom
10–15 Nov
4.98 out of 5 average rating, 162 reviews
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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, 397 reviews