filters

Search results; 158 homes in Winchester

Home in Winchester
Charming Country Retreat
4 bedrooms, 5 beds, 1 private bathroom
21–26 Aug
,
Guest favourite
Loft in Winchester
The Bike Flat
2 bedrooms, 5 beds, 1 bathroom
23–28 Aug
4.92 out of 5 average rating, 185 reviews
Flat in Winchester
The Primrose inside historic commercial bldg
2 bedrooms, 3 beds, 1 bathroom
21–26 Aug
4.93 out of 5 average rating, 75 reviews
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 Winchester
Container Home GREAT Countryside Views COZY Stay
1 bedroom, 1 king bed, 1 bathroom
24–29 Aug
4.96 out of 5 average rating, 198 reviews
Top guest favourite
Cabin in Jacksonville
Bunkhouse Seventy-Four
1 bedroom, 1 queen bed, 1 bathroom
24–29 Aug
4.98 out of 5 average rating, 411 reviews
Guest favourite
Home in White Hall
The Humble Hideaway
3 bedrooms, 3 beds, 2 bathrooms
23–28 Aug
4.91 out of 5 average rating, 109 reviews
Top guest favourite
Cabin in Jacksonville
Audrey's Abode
2 bedrooms, 4 beds, 1 bathroom
19–24 Oct
4.97 out of 5 average rating, 784 reviews
Top guest favourite
Home in White Hall
Cozy-Rose-Cottage
2 bedrooms, 3 beds, 1 bathroom
22–27 Aug
4.92 out of 5 average rating, 90 reviews
Home in Pittsfield
Newly remodeled home
2 bedrooms, 2 queen beds, 1 bathroom
23–28 Aug
4.87 out of 5 average rating, 55 reviews
Guest favourite
Home in Beardstown
Nostalgia on 5th St
4 bedrooms, 6 beds, 2 bathrooms
23–28 Aug
4.9 out of 5 average rating, 40 reviews
Home in Alsey
Douglas Street Retreat
4 bedrooms, 5 beds, 2.5 bathrooms
13–18 Sept
4.8 out of 5 average rating, 15 reviews
Guest favourite
Flat in Pittsfield
Pike County Haven: Retro Loft
1 bedroom, 2 beds, 1 bathroom
19–24 Aug
5.0 out of 5 average rating, 22 reviews
Home in Carrollton
Cozy home in picturesque small town
3 bedrooms, 3 beds, 2 bathrooms
30 Sept – 5 Oct
4.82 out of 5 average rating, 185 reviews
Superhost
Flat in Pittsfield
Dome View Loft
2 bedrooms, 2 beds, 1 bathroom
30 Aug – 4 Sept
4.8 out of 5 average rating, 15 reviews
Cabin in Elsberry
Relaxing Log Home Getaway
3 bedrooms, 7 beds, 4 bathrooms
19–24 Aug
5.0 out of 5 average rating, 32 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
Guest favourite
Cabin in Kampsville
Farm Stay in Illinois with Private Fishing Pond
1 bedroom, 3 queen beds, 1 bathroom
20–25 Aug
5.0 out of 5 average rating, 19 reviews
Top guest favourite
Guest house in Jerseyville
Cozy cabin on farm near Jerseyville and Grafton IL
2 bedrooms, 4 beds, 1 bathroom
13–18 Sept
4.96 out of 5 average rating, 197 reviews