Vacation rentals in Winchester
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Top-rated vacation rentals in Winchester
Guests agree: these stays are highly rated for location, cleanliness, and more.
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Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Winchester vacation rentals
Other great vacation rentals in Winchester
Guest favorite
Guest suite in Melrose
4.85 out of 5 average rating, 247 reviewsGuest Suite with separate entrance
Guest favorite
Guest suite in Tyngsborough
4.98 out of 5 average rating, 219 reviewsLakefront Suite Two-Room, Comfy, Tranquil
Guest favorite
Cottage in Arlington
4.94 out of 5 average rating, 131 reviewsHistoric 1870 Carriage House
Guest favorite
Guest suite in Arlington
5.0 out of 5 average rating, 101 reviews2BR Suite - Bright - Modern - Central AC - Parking
Guest favorite
Apartment in Lexington
4.94 out of 5 average rating, 342 reviewsWarm home in Lexington, walk to town, nature trail
Guest favorite
Guesthouse in Framingham
4.98 out of 5 average rating, 207 reviewsPrivate guest house on beautiful country road
Guest favorite
Home in Lynn
4.91 out of 5 average rating, 228 reviewsClean, spacious In-Law Suite -Near Everything
Guest favorite
Guest suite in Newton
4.98 out of 5 average rating, 565 reviewsSpacious suite with private entrance, parking spot
Quick stats about vacation rentals in Winchester
Total rentals
20 properties
Popular amenities
Kitchen, Wifi, and Pool
Wifi availability
20 properties include access to wifi
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Total number of reviews
940 reviews
Nightly prices starting at
ﺩ.ﺇ110 before taxes and fees
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