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Search results; 145 homes in Winchester

Top guest favourite
Cabin in Winchester
Container Home GREAT Countryside Views COZY Stay
1 bedroom, 1 bed, 1 private bathroom
24–29 Aug
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4.96 out of 5 average rating, 196 reviews
Guest favourite
Loft in Winchester
The Bike Flat
2 bedrooms, 5 beds, 1 bathroom
23–28 Aug
4.92 out of 5 average rating, 182 reviews
Flat in Winchester
The Primrose inside historic commercial bldg
2 bedrooms, 3 beds, 1 bathroom
11–16 Aug
4.93 out of 5 average rating, 75 reviews
Home in Winchester
Charming Country Retreat
4 bedrooms, 5 beds, 1 bathroom
10–15 Aug
New place to stay
Guest favourite
Flat in Winchester
Sugar Shack, a retro studio apartment
1 bedroom, 1 queen bed, 1 bathroom
2–7 Oct
4.89 out of 5 average rating, 54 reviews
Top guest favourite
Cabin in Jacksonville
Bunkhouse Seventy-Four
1 bedroom, 1 queen bed, 1 bathroom
9–14 Aug
4.98 out of 5 average rating, 410 reviews
Top guest favourite
Cabin in Jacksonville
Audrey's Abode
2 bedrooms, 4 beds, 1 bathroom
4–9 Oct
4.97 out of 5 average rating, 781 reviews
Guest favourite
Home in White Hall
The Humble Hideaway
3 bedrooms, 3 beds, 2 bathrooms
9–14 Aug
4.91 out of 5 average rating, 107 reviews
Top guest favourite
Loft in Virginia
Two Doors Down Loft, Virginia-Lincoln territory!
2 queen beds, 1.5 bathrooms
1–6 Sept
4.95 out of 5 average rating, 212 reviews
Top guest favourite
Flat in Murrayville
Peace on the Prairie - Studio Apartment
1 bedroom, 4 beds, 1 bathroom
1–6 Sept
4.97 out of 5 average rating, 432 reviews
Guest favourite
Guest suite in Pittsfield
Florence Guest House--Loft Unit
1 bedroom, 3 beds, 1 bathroom
29 Aug – 3 Sept
4.82 out of 5 average rating, 139 reviews
Superhost
Cabin in Hillview
Modern-Rustic Cabin, Nature Inspired
2 beds, 1 bathroom
8–13 Aug
4.86 out of 5 average rating, 49 reviews
Top guest favourite
Home in White Hall
Cozy-Rose-Cottage
2 bedrooms, 3 beds, 1 bathroom
17–22 Aug
4.92 out of 5 average rating, 89 reviews
Home in Pittsfield
Newly remodeled home
2 bedrooms, 2 queen beds, 1 bathroom
9–14 Aug
4.87 out of 5 average rating, 55 reviews
Guest favourite
Home in Pittsfield
Florence Guest House
3 bedrooms, 5 beds, 2 bathrooms
17–22 Sept
4.84 out of 5 average rating, 256 reviews
Top guest favourite
Flat in Beardstown
The VanderWaal
2 bedrooms, 2 beds, 1 bathroom
17–22 Aug
5.0 out of 5 average rating, 27 reviews
Top guest favourite
Holiday home in Meredosia
Scenic 3 bedroom Wildlife Retreat
3 bedrooms, 5 beds, 1 bathroom
12–17 Aug
4.98 out of 5 average rating, 97 reviews
Top guest favourite
Home in Mount Sterling
Cozy Cottage 405
2 bedrooms, 2 queen beds, 1 bathroom
12–17 Aug
4.94 out of 5 average rating, 17 reviews
Room in Pittsfield
Boutique Queen Suite I Private Bath + Fast WiFi
1 bed, 1.5 bathrooms
16–21 Aug
New place to stay