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Search results; 161 homes in Winchester

Top guest favourite
Cabin in Winchester
Container Home GREAT Countryside Views COZY Stay
1 bedroom, 1 bed, 1 private bathroom
13–18 Sept
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4.96 out of 5 average rating, 199 reviews
Guest favourite
Loft in Winchester
The Bike Flat
2 bedrooms, 5 beds, 1 bathroom
15–20 Nov
4.92 out of 5 average rating, 186 reviews
Flat in Winchester
The Primrose inside historic commercial bldg
2 bedrooms, 3 beds, 1 bathroom
15–20 Sept
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
6–11 Oct
4.89 out of 5 average rating, 54 reviews
Home in Winchester
Charming Country Retreat
4 bedrooms, 5 beds, 1 bathroom
12–17 Sept
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
Top guest favourite
Cabin in Jacksonville
Audrey's Abode
2 bedrooms, 4 beds, 1 bathroom
20–25 Sept
4.97 out of 5 average rating, 787 reviews
Top guest favourite
Cabin in Jacksonville
Bunkhouse Seventy-Four
1 bedroom, 1 queen bed, 1 bathroom
13–18 Sept
4.98 out of 5 average rating, 415 reviews
Guest favourite
Home in White Hall
The Humble Hideaway
3 bedrooms, 3 beds, 2 bathrooms
20–25 Sept
4.91 out of 5 average rating, 113 reviews
Guest favourite
Home in Pittsfield
Florence Guest House
3 bedrooms, 5 beds, 2 bathrooms
18–23 Sept
4.84 out of 5 average rating, 256 reviews
Cabin in Pittsfield
Cozy Country Cabin Perfect for Families & Retreats
5 bedrooms, 8 beds, 5 bathrooms
12–17 Sept
4.74 out of 5 average rating, 23 reviews
Top guest favourite
Home in White Hall
Cozy-Rose-Cottage
2 bedrooms, 3 beds, 1 bathroom
12–17 Sept
4.91 out of 5 average rating, 93 reviews
Home in Pittsfield
Newly remodeled home
2 bedrooms, 2 queen beds, 1 bathroom
20–25 Sept
4.88 out of 5 average rating, 56 reviews
Guest favourite
Guest suite in Pittsfield
Florence Guest House--Loft Unit
1 bedroom, 3 beds, 1 bathroom
18–23 Sept
4.81 out of 5 average rating, 140 reviews
Home in Carrollton
Cozy home in picturesque small town
3 bedrooms, 3 beds, 2 bathrooms
16–21 Sept
4.82 out of 5 average rating, 185 reviews
Guest favourite
Home in Beardstown
Nostalgia on 5th St
4 bedrooms, 6 beds, 2 bathrooms
3–8 Oct
4.91 out of 5 average rating, 44 reviews
Guest favourite
Cottage in Pearl
Beautiful Secluded Home With a breathtaking view
3 bedrooms, 5 beds, 2 bathrooms
12–17 Sept
4.96 out of 5 average rating, 98 reviews
Guest favourite
Home in Roodhouse
Cozy Corner Bungalow
2 bedrooms, 4 beds, 1 bathroom
12–17 Sept
4.9 out of 5 average rating, 42 reviews
Guest favourite
Home in Pittsfield Hill
Full Country Home Pittsfield, Illinois
2 bedrooms, 4 beds, No bathroom
13–18 Sept
4.9 out of 5 average rating, 39 reviews