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.
Holiday rentals for every style
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Popular amenities for Winchester holiday rentals
Other great holiday rentals in Winchester
Flat in Concord
4.94 out of 5 average rating, 207 reviewsBishop Suite - Private suite in historic Concord
27 Mar – 3 Apr
Guest suite in Arlington
4.92 out of 5 average rating, 158 reviewsCozy 1 bed apt Cambridge/Somerville/Arlington line
16–23 Nov
Flat in Cambridge
4.97 out of 5 average rating, 285 reviewsPicture-perfect Cambridge guest apartment, parking
19–24 Aug
Guest suite in Newton
4.97 out of 5 average rating, 558 reviewsSpacious suite with private entrance, parking spot
30 Sep – 7 Oct
Flat in Natick
4.98 out of 5 average rating, 333 reviewsScandi-Modern Apartment
24–31 Oct
Barn in Carlisle
4.84 out of 5 average rating, 513 reviews✨Entire Secluded Barn Suite Ctr Historic Carlisle✨
10–17 Feb
Guest suite in Littleton
4.91 out of 5 average rating, 315 reviewsHistoric Loft with bathroom & kitchenette
13–20 Sep
Guest suite in Tyngsborough
4.98 out of 5 average rating, 217 reviewsLakefront Suite Two-Room, Comfy, Tranquil
7–14 Aug
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
₹2,501 before taxes and fees
Destinations to explore
- Cape Cod Holiday rentals
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