Holiday rentals in Winchester
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Top-rated holiday rentals in Winchester
Guests agree: these stays are highly rated for location, cleanliness and more.
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Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Winchester holiday rentals
Other great holiday rentals in Winchester
Guest favourite
Guest suite in Newton
4.97 out of 5 average rating, 556 reviewsSpacious suite with private entrance, parking spot
3–10 Oct
$183 SGD per night
Guest favourite
Home in Lynn
4.91 out of 5 average rating, 226 reviewsClean, spacious In-Law Suite -Near Everything
17–24 Feb
$202 SGD per night
Guest favourite
Home in Medford
4.95 out of 5 average rating, 126 reviewsSingle family home near Tufts,DT Boston,w/ parking
16–23 Aug
$1,100 SGD per night
Guest favourite
Guest suite in Tyngsborough
4.98 out of 5 average rating, 216 reviewsLakefront Suite Two-Room, Comfy, Tranquil
2–9 Aug
$174 SGD per night
Guest favourite
Barn in Carlisle
4.87 out of 5 average rating, 361 reviews✨Private Studio w/ Loft Center Historic Carlisle✨
5–12 Dec
$172 SGD per night
Guest favourite
Flat in Natick
4.98 out of 5 average rating, 332 reviewsScandi-Modern Apartment
11–18 Oct
$177 SGD per night
Guest favourite
Flat in Somerville
4.91 out of 5 average rating, 170 reviewsSpacious, private apartment in perfect location
17–24 Aug
$228 SGD per night
Guest favourite
Guest house in Framingham
4.98 out of 5 average rating, 201 reviewsPrivate guest house on beautiful country road
10–17 Feb
$154 SGD per night
Quick stats about holiday 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 SGD before taxes and fees
Destinations to explore
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