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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
29 Oct – 3 Nov
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4.95 out of 5 average rating, 87 reviews
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Guest favourite
Flat in Winchester
Winchester Apartment on Greenway
1 bedroom, 1 bed
9–14 Dec
4.96 out of 5 average rating, 73 reviews
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Guest favourite
Room in Winchester
Private Suite with Full Bath & Separate Entrance
1 king bed
13–20 Oct
5.0 out of 5 average rating, 8 reviews
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Top guest favourite
Home in Woburn
Stone Cottage with meadow view
3 bedrooms, 3 beds
25–30 Oct
4.95 out of 5 average rating, 189 reviews
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Guest favourite
Guest suite in Arlington
3 Bedroom 2nd Floor Unit - commute to Boston
3 bedrooms, 3 beds
18–23 Oct
4.88 out of 5 average rating, 57 reviews
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Top guest favourite
Guest suite in Lexington
Modern Farmhouse Suite in Historic Lexington
2 bedrooms, 3 beds
1–6 Oct
4.97 out of 5 average rating, 189 reviews
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Guest favourite
Home in Stoneham
Stylish Stoneham Getaway Playground Game Room
5 bedrooms, 6 beds
19–24 Oct
4.95 out of 5 average rating, 22 reviews
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Top guest favourite
Flat in Arlington
Lakeside apartment, patio, hot tub, outside shower
1 bedroom, 2 beds
10–15 Oct
4.98 out of 5 average rating, 221 reviews
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Top guest favourite
Flat in Woburn
Comfy-Spacious-private 1BR conveniently located
1 bedroom, 2 beds
5–10 Nov
4.95 out of 5 average rating, 256 reviews
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Guest favourite
Flat in Lexington
Warm home in Lexington, walk to town, nature trail
2 bedrooms, 2 beds
1–6 Nov
4.94 out of 5 average rating, 465 reviews
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Top guest favourite
Home in Somerville
6BR2Bath LUXE HOME
6 bedrooms, 8 beds
15–20 Nov
5.0 out of 5 average rating, 23 reviews
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Featured hotel
Hotel in Burlington
Sonesta Simply Suites Boston Burlington, Studio s.
1 bedroom, 1 queen bed
11–16 Oct
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Top guest favourite
Home in Stoneham
Quiet Boston-Area Sanctuary, Elegant & Comfortable
5 bedrooms, 6 beds
24–29 Oct
4.97 out of 5 average rating, 36 reviews
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Top guest favourite
Guest suite in Woburn
Private apartment with driveway parking in Woburn
1 bedroom, 1 queen bed
26–31 Oct
4.97 out of 5 average rating, 192 reviews
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Top guest favourite
Flat in Stoneham
Entire guest suite in Stoneham
1 bedroom, 1 queen bed
29 Nov – 4 Dec
4.88 out of 5 average rating, 455 reviews
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Top guest favourite
Flat in Arlington
Cheerful 1-bedroom home with free parking
1 bedroom, 1 queen bed
11–16 Nov
4.98 out of 5 average rating, 80 reviews
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Top guest favourite
Home in Woburn
Large 4Bed 2Bath Clean Alternative to Hotel Living
4 bedrooms, 4 queen beds
1–6 Nov
4.9 out of 5 average rating, 175 reviews
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Top guest favourite
Flat in Arlington
New Clean 3Br Arlington Heights Condo Walk to Shop
3 bedrooms, 3 beds
31 Oct – 5 Nov
4.95 out of 5 average rating, 98 reviews
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Room in Arlington
Sleek Private Studio • Near Arlington Center
1 bed
1–6 Nov
New place to stay