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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
14–19 Aug
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4.92 out of 5 average rating, 179 reviews
Guest favourite
Flat in Winchester
Sugar Shack, a retro studio apartment
1 bedroom, 1 queen bed, 1 bathroom
21–26 Jul
4.89 out of 5 average rating, 54 reviews
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
Home in Winchester
Charming Country Retreat
4 bedrooms, 5 beds, 1 bathroom
2–7 Aug
New place to stay
Top guest favourite
Cabin in Winchester
Container Home GREAT Countryside Views COZY Stay
1 bedroom, 1 king bed, 1 bathroom
2–7 Aug
4.96 out of 5 average rating, 192 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, 406 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, 777 reviews
Home in Alsey
Douglas Street Retreat
4 bedrooms, 5 beds, 2.5 bathrooms
24–29 Jul
4.79 out of 5 average rating, 14 reviews
Guest favourite
Home in White Hall
Cozy-Rose-Cottage
2 bedrooms, 3 beds, 1 bathroom
21–26 Jul
4.92 out of 5 average rating, 88 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, 104 reviews
Top guest favourite
Home in Beardstown
My Little Bungalow on Monroe Street.
2 bedrooms, 5 beds, 1.5 bathrooms
2–7 Aug
4.98 out of 5 average rating, 320 reviews
Room in Pittsfield
Boutique Queen Suite I Private Bath + Fast WiFi
1 bed, 1.5 bathrooms
26–31 Jul
New place to stay
Guest favourite
Home in Roodhouse
Cozy Corner Bungalow
2 bedrooms, 4 beds, 1 bathroom
21–26 Jul
4.92 out of 5 average rating, 39 reviews
Superhost
Flat in Pittsfield
Dome View Loft
2 bedrooms, 2 beds, 1 bathroom
23–28 Jul
4.79 out of 5 average rating, 14 reviews
Guest favourite
Rooms in Pittsfield
Sloth Lodging (Upper Level)
3 bedrooms, 3 beds, 1 bathroom
21–26 Jul
4.91 out of 5 average rating, 53 reviews
Guest favourite
Cottage in Pearl
Beautiful Secluded Home With a breathtaking view
3 bedrooms, 5 beds, 2 bathrooms
26–31 Jul
4.96 out of 5 average rating, 96 reviews
Home in Carrollton
Cozy home in picturesque small town
3 bedrooms, 3 beds, 2 bathrooms
5–10 Aug
4.82 out of 5 average rating, 184 reviews
Guest favourite
Hotel in Jacksonville
Charming downtown hotel above wine bar - Room 1
1 bedroom, 1 bed, 1 bathroom
21–26 Jul
4.95 out of 5 average rating, 154 reviews
Home in Chambersburg
Burnt Oaks Farm House
3 bedrooms, 4 beds, 2 bathrooms
26–31 Jul