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Search results; 145 homes in Winchester

Guest favourite
Loft in Winchester
The Bike Flat
2 bedrooms, 5 beds, 1 private bathroom
16–21 Aug
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4.92 out of 5 average rating, 182 reviews
Flat in Winchester
The Primrose inside historic commercial bldg
2 bedrooms, 3 beds
7–12 Aug
4.96 out of 5 average rating, 73 reviews
Home in Winchester
Charming Country Retreat
4 bedrooms, 5 beds
2–7 Aug
New place to stay
Guest favourite
Flat in Winchester
Sugar Shack, a retro studio apartment
1 bedroom, 1 queen bed
5–10 Aug
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
2–7 Aug
4.96 out of 5 average rating, 194 reviews
Top guest favourite
Cabin in Jacksonville
Bunkhouse Seventy-Four
1 bedroom, 1 queen bed
1–6 Aug
4.98 out of 5 average rating, 406 reviews
Home in Alsey
Douglas Street Retreat
4 bedrooms, 5 beds
3–8 Aug
4.8 out of 5 average rating, 15 reviews
Top guest favourite
Cabin in Jacksonville
Audrey's Abode
2 bedrooms, 4 beds
4–9 Oct
4.97 out of 5 average rating, 779 reviews
Guest favourite
Home in White Hall
The Humble Hideaway
3 bedrooms, 3 beds
9–14 Aug
4.92 out of 5 average rating, 106 reviews
Top guest favourite
Loft in Virginia
Two Doors Down Loft, Virginia-Lincoln territory!
2 queen beds
11–16 Aug
4.95 out of 5 average rating, 210 reviews
Guest favourite
Home in Pittsfield Hill
Full Country Home Pittsfield, Illinois
2 bedrooms, 4 beds
9–14 Aug
4.94 out of 5 average rating, 32 reviews
Room in Pittsfield
Boutique Queen Suite I Private Bath + Fast WiFi
1 bed
16–21 Aug
New place to stay
Home in Pittsfield
Newly remodeled home
2 bedrooms, 2 queen beds
2–7 Aug
4.87 out of 5 average rating, 55 reviews
Guest favourite
Home in White Hall
Cozy-Rose-Cottage
2 bedrooms, 3 beds
3–8 Aug
4.92 out of 5 average rating, 88 reviews
Guest favourite
Home in Roodhouse
Cozy Corner Bungalow
2 bedrooms, 4 beds
2–7 Aug
4.92 out of 5 average rating, 39 reviews
Guest favourite
Home in Jacksonville
Rees Residential
2 bedrooms, 3 beds
16–21 Aug
4.85 out of 5 average rating, 48 reviews
Guest favourite
Home in Beardstown
Nostalgia on 5th St
4 bedrooms, 6 beds
2–7 Aug
4.89 out of 5 average rating, 37 reviews
Top guest favourite
Home in Beardstown
House of Blessings
2 bedrooms, 3 beds
2–7 Aug
4.99 out of 5 average rating, 91 reviews
Top guest favourite
Flat in Murrayville
Peace on the Prairie - Studio Apartment
1 bedroom, 4 beds
1–6 Sept
4.97 out of 5 average rating, 432 reviews