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Search results; 155 homes in Winchester

Guest favourite
Loft in Winchester
The Bike Flat
2 bedrooms, 5 beds, 1 private bathroom
9–14 Aug
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4.93 out of 5 average rating, 174 reviews
Home in Winchester
Charming Country Retreat
New place to stay, 4 bedrooms, 5 beds, 1 bathroom
5–10 Jul
Flat in Winchester
The Primrose inside historic commercial bldg
4.96 out of 5 average rating, 72 reviews, 2 bedrooms, 3 beds, 1 bathroom
3–8 Aug
Guest favourite
Flat in Winchester
Sugar Shack, a retro studio apartment
4.89 out of 5 average rating, 54 reviews, 1 bedroom, 1 bed, 1 bathroom
7–12 Jul
Top guest favourite
Cabin in Winchester
Container Home GREAT Countryside Views COZY Stay
4.96 out of 5 average rating, 190 reviews, 1 bedroom, 1 bed, 1 bathroom
13–18 Jul
Top guest favourite
Cabin in Jacksonville
Audrey's Abode
4.97 out of 5 average rating, 775 reviews, 2 bedrooms, 4 beds, 1 bathroom
8–13 Jul
Top guest favourite
Home in Pittsfield
Florence Guest House
4.85 out of 5 average rating, 254 reviews, 3 bedrooms, 5 beds, 2 bathrooms
6–11 Jul
Home in Alsey
Douglas Street Retreat
4.83 out of 5 average rating, 12 reviews, 4 bedrooms, 5 beds, 2.5 bathrooms
8–13 Jul
Guest favourite
Home in White Hall
The Humble Hideaway
4.91 out of 5 average rating, 102 reviews, 3 bedrooms, 3 beds, 2 bathrooms
9–14 Jul
Top guest favourite
Cabin in Jacksonville
Bunkhouse Seventy-Four
4.98 out of 5 average rating, 402 reviews, 1 bedroom, 1 bed, 1 bathroom
12–17 Jul
Guest favourite
Home in Roodhouse
Cozy Corner Bungalow
4.92 out of 5 average rating, 38 reviews, 2 bedrooms, 4 beds, 1 bathroom
12–17 Jul
Guest favourite
Flat in Pittsfield
Dome View Loft
5.0 out of 5 average rating, 11 reviews, 2 bedrooms, 2 beds, 1 bathroom
4–9 Jul
Guest favourite
Guest suite in Pittsfield
Florence Guest House--Loft Unit
4.82 out of 5 average rating, 139 reviews, 1 bedroom, 3 beds, 1 bathroom
12–17 Jul
Flat in Jacksonville
Baker & Birch
New place to stay, 2 bedrooms, 3 beds, 1 bathroom
4–9 Jul
Guest favourite
Cottage in Pearl
Beautiful Secluded Home With a breathtaking view
4.96 out of 5 average rating, 94 reviews, 3 bedrooms, 5 beds, 2 bathrooms
5–10 Jul
Cabin in Belleview
Illinois Rustic Getaway!! Pike County,IL
4.79 out of 5 average rating, 24 reviews, 4 bedrooms, 5 beds, 2.5 bathrooms
10–15 Jul
Top guest favourite
Home in Pleasant Plains
Hay Rake Country Acres-Peaceful Getaway-Sleeps 8
5.0 out of 5 average rating, 12 reviews, 4 bedrooms, 5 beds, 2 bathrooms
4–9 Jul
Top guest favourite
Barn in Jacksonville
Basketball Pickleball +Party Room + Loft Sleeps 17
4.97 out of 5 average rating, 97 reviews, 2 bedrooms, 16 beds, 1.5 bathrooms
4–9 Jul
Top guest favourite
Farm stay in Carrollton
Peaceful Country Stay- The Carrollton Farmhouse
5.0 out of 5 average rating, 49 reviews, 3 bedrooms, 5 beds, 1.5 bathrooms
6–11 Jul