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Search results; 153 homes in Winchester

Guest favourite
Loft in Winchester
The Bike Flat
2 bedrooms, 5 beds, 1 private bathroom
22–27 Jul
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4.93 out of 5 average rating, 175 reviews
Home in Winchester
Charming Country Retreat
4 bedrooms, 5 beds, 1 bathroom
26–31 Jul
New place to stay
Flat in Winchester
The Primrose inside historic commercial bldg
2 bedrooms, 3 beds, 1 bathroom
3–8 Aug
4.96 out of 5 average rating, 73 reviews
Guest favourite
Flat in Winchester
Sugar Shack, a retro studio apartment
1 bedroom, 1 queen bed, 1 bathroom
20–25 Jul
4.89 out of 5 average rating, 54 reviews
Top guest favourite
Cabin in Winchester
Container Home GREAT Countryside Views COZY Stay
1 bedroom, 1 king bed, 1 bathroom
19–24 Jul
4.96 out of 5 average rating, 190 reviews
Guest favourite
Home in Pittsfield
Florence Guest House
3 bedrooms, 5 beds, 2 bathrooms
12–17 Jul
4.84 out of 5 average rating, 256 reviews
Home in Alsey
Douglas Street Retreat
4 bedrooms, 5 beds, 2.5 bathrooms
21–26 Jul
4.77 out of 5 average rating, 13 reviews
Top guest favourite
Cabin in Jacksonville
Bunkhouse Seventy-Four
1 bedroom, 1 queen bed, 1 bathroom
30 Jul – 4 Aug
4.98 out of 5 average rating, 403 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, 776 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, 103 reviews
Guest favourite
Guest suite in Pittsfield
Florence Guest House--Loft Unit
1 bedroom, 3 beds, 1 bathroom
12–17 Jul
4.82 out of 5 average rating, 139 reviews
Guest favourite
Home in Roodhouse
Cozy Corner Bungalow
2 bedrooms, 4 beds, 1 bathroom
12–17 Jul
4.92 out of 5 average rating, 38 reviews
Top guest favourite
Home in White Hall
Cozy-Rose-Cottage
2 bedrooms, 3 beds, 1 bathroom
14–19 Jul
4.92 out of 5 average rating, 87 reviews
Guest favourite
Home in Jacksonville
Rees Residential
2 bedrooms, 3 beds, 1 bathroom
13–18 Jul
4.85 out of 5 average rating, 46 reviews
Top guest favourite
Cabin in Kampsville
Exotic Animal Farm Stay in Illinois: Tour, Explore
1 bedroom, 3 queen beds, 1 bathroom
12–17 Jul
5.0 out of 5 average rating, 19 reviews
Top guest favourite
Barn in Jacksonville
Basketball Pickleball +Party Room + Loft Sleeps 17
2 bedrooms, 16 beds, 1.5 bathrooms
13–18 Jul
4.97 out of 5 average rating, 97 reviews
Flat in Jacksonville
Baker & Birch
2 bedrooms, 3 beds, 1 bathroom
12–17 Jul
New place to stay
Guest favourite
Cottage in Pearl
Beautiful Secluded Home With a breathtaking view
3 bedrooms, 5 beds, 2 bathrooms
12–17 Jul
4.96 out of 5 average rating, 96 reviews
Home in Pittsfield
Newly remodeled home
2 bedrooms, 2 queen beds, 1 bathroom
12–17 Jul
4.87 out of 5 average rating, 54 reviews