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Holiday houses in Winchester
Find and book unique accommodation on Airbnb
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
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Popular amenities for Winchester holiday rentals
Other great holiday rentals in Winchester
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Guest favourite
Tiny home in Johnstown
4.89 out of 5 average rating, 169 reviewsHook wine and sinker
![](https://a0.muscache.com/im/pictures/miso/Hosting-588255413815757004/original/3bdea991-9fed-41ea-af87-66b744ff742a.jpeg?im_w=720)
Guest favourite
Home in Ottawa
4.93 out of 5 average rating, 171 reviewsSpacious Walk-Out Basement with Scenic Views
![](https://a0.muscache.com/im/pictures/miso/Hosting-671931974087502137/original/b0e0cf4e-840a-491c-ad2a-a1a1c55419e9.jpeg?im_w=720)
Guest favourite
Home in Vankleek Hill, Canada
4.99 out of 5 average rating, 105 reviewsModern Country Suite Near Prescott-Russell Trail
![](https://a0.muscache.com/im/pictures/38ec47f0-4759-47df-9506-1c50bcec86cf.jpg?im_w=720)
Guest favourite
Farm stay in Williamstown, Canada
4.95 out of 5 average rating, 121 reviewsRefreshing Farmstay near Cornwall
![](https://a0.muscache.com/im/pictures/hosting/Hosting-949590639386764702/original/db2b8074-fe89-49dc-9b8c-0b97184cb49b.jpeg?im_w=720)
Guest favourite
Farm stay in Chesterville
4.98 out of 5 average rating, 83 reviewsCountryside Farm-stay | Studio with sleeping loft
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Guest favourite
Apartment in Embrun, Canada
4.93 out of 5 average rating, 41 reviewsFabulous Retreat with Hot Tub
![](https://a0.muscache.com/im/pictures/64a55853-9927-4a8f-b959-afd02b232fbf.jpg?im_w=720)
Guest favourite
Apartment in Russell
4.93 out of 5 average rating, 58 reviewsPrivate luxurious 2bd suite near Ottawa w/ parking
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Guest favourite
Tiny home in Crysler, Canada
5.0 out of 5 average rating, 18 reviewsDelightful countryside 1-bedroom bunkie
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