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.
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 suite in Newton
4.97 out of 5 average rating, 556 reviewsSpacious suite with private entrance, parking spot
Oct. 3 – 10
Home in Lynn
4.91 out of 5 average rating, 226 reviewsClean, spacious In-Law Suite -Near Everything
Feb. 17 – 24
Home in Medford
4.95 out of 5 average rating, 126 reviewsSingle family home near Tufts,DT Boston,w/ parking
Aug. 16 – 23
Guest suite in Tyngsborough
4.98 out of 5 average rating, 216 reviewsLakefront Suite Two-Room, Comfy, Tranquil
Aug. 2 – 9
Barn in Carlisle
4.87 out of 5 average rating, 361 reviews✨Private Studio w/ Loft Center Historic Carlisle✨
Dec. 5 – 12
Apartment in Natick
4.98 out of 5 average rating, 332 reviewsScandi-Modern Apartment
Oct. 11 – 18
Apartment in Somerville
4.91 out of 5 average rating, 170 reviewsSpacious, private apartment in perfect location
Aug. 17 – 24
Guesthouse in Framingham
4.98 out of 5 average rating, 201 reviewsPrivate guest house on beautiful country road
Feb. 10 – 17
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
$41 CAD before taxes and fees
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