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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
16–21 Sept
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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, 1 bathroom
17–22 Nov
4.96 out of 5 average rating, 71 reviews
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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
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Featured hotel
Hotel in Burlington
Studio suite - queen - mobility accessible - tub
1 bedroom, 1 queen bed, 1 bathroom
21–26 Sept
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Featured hotel
Hotel in Cambridge
Queen ADA, patio
1 bedroom, 1 queen bed, 1 bathroom
11–16 Dec
5.0 out of 5 average rating, 7 reviews
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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
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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, 125 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, 396 reviews
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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, 12 reviews
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Top guest favourite
Home in Medford
Cozy & Modern 2 Bedroom House - Free Parking !
2 bedrooms, 2 queen beds, 1 bathroom
1–6 Nov
4.94 out of 5 average rating, 161 reviews
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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
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Top guest favourite
Home in Lexington
Lexington Battle Green
3 bedrooms, 3 beds, 3 bathrooms
17–22 Sept
4.96 out of 5 average rating, 25 reviews
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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
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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
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Top guest favourite
Home in Medford
Queen Anne Victorian in Excellent Location
3 bedrooms, 3 beds, 2 bathrooms
17–22 Sept
4.85 out of 5 average rating, 139 reviews
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Top guest favourite
Home in Arlington
The Brickhouz at Arlington !
4 bedrooms, 6 beds, 2 bathrooms
15–20 Nov
4.99 out of 5 average rating, 118 reviews
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Flat in Arlington
Spacious Luxury Two-Level Home in East Arlington
4 bedrooms, 4 beds, 3 bathrooms
28 Sept – 3 Oct
New place to stay
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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
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Top guest favourite
Flat in Arlington
Lakeside apartment, patio, hot tub, outside shower
1 bedroom, 2 beds, 1 bathroom
3–8 Dec
4.98 out of 5 average rating, 221 reviews