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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
Get the amount of space that is right for you
Popular amenities for Winchester holiday rentals
Other great holiday rentals in Winchester
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Guest favourite
Home in Greenville
4.89 out of 5 average rating, 138 reviews17 Lakes,Swimming Beach, Dogs,Family,Very SpaciouS
![](https://a0.muscache.com/im/pictures/c20fb84e-a706-4bd0-aba4-544220f358a0.jpg?im_w=720)
Guest favourite
Guesthouse in Liberty
4.9 out of 5 average rating, 328 reviewsCool off in the country!
![](https://a0.muscache.com/im/pictures/miso/Hosting-640080238144070627/original/f1d870a3-e504-4ef6-ae00-921b54836646.jpeg?im_w=720)
Guest favourite
Farm stay in Redkey
4.89 out of 5 average rating, 37 reviewsThe Redkey Roost. Historic home built in 1863.
![](https://a0.muscache.com/im/pictures/miso/Hosting-52793540/original/30de961e-eb0a-4c61-b548-e4341ccb60a4.jpeg?im_w=720)
Guest favourite
Apartment in Hagerstown
4.89 out of 5 average rating, 98 reviewsNewly renovated studio in Hagerstown-Self Check-in
![](https://a0.muscache.com/im/pictures/hosting/Hosting-961065701679237747/original/a922e7f0-275e-4a39-8e15-e71d9adc8248.jpeg?im_w=720)
Guest favourite
Home in Greenville
5.0 out of 5 average rating, 24 reviewsThe Blu Door Suite @ G-Vegas
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Guest favourite
Guesthouse in Richmond
5.0 out of 5 average rating, 45 reviewsJustice Gästehaus
![](https://a0.muscache.com/im/pictures/82df3e3c-7366-4a0d-ac5e-9e92c9f12aa2.jpg?im_w=720)
Guest favourite
Bungalow in Richmond
4.91 out of 5 average rating, 58 reviewsBoho Bungalow off Main-one block from Lovely Park
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Guest favourite
Home in Muncie
5.0 out of 5 average rating, 21 reviewsQuaint Quarters on 26th.
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