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Search results; Over 1,000 homes in Winchester

Guest favourite
Cottage in Winchester
Secluded Mountain Top Retreat | Stunning Views
1 bedroom, 2 beds, 1 private bathroom
23–28 Aug
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4.88 out of 5 average rating, 41 reviews
Top guest favourite
Flat in Winchester
Downtowner
4.97 out of 5 average rating, 354 reviews, 2 bedrooms, 3 beds, 1 bathroom
2–7 Aug
Top guest favourite
Flat in Winchester
Old Town Modern Twist! Rock n’ Roll FUN w/Parking!
4.95 out of 5 average rating, 203 reviews, 2 bedrooms, 2 beds, 1 bathroom
15–20 Aug
Top guest favourite
Cottage in Winchester
COZY+SEXY Private Country Escape! HOT TUB & Views~
4.99 out of 5 average rating, 481 reviews, 1 bedroom, 1 bed, 1 bathroom
16–21 Aug
Top guest favourite
Home in Winchester
Cameron Charmer pristine w/double master suites
4.98 out of 5 average rating, 221 reviews, 2 bedrooms, 2 beds, 2.5 bathrooms
2–7 Aug
Top guest favourite
Home in Winchester
Colonial Getaway Near Old Town Historic Winchester
4.98 out of 5 average rating, 246 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
4–9 Sept
Top guest favourite
Room in Winchester
Winchester Private Room
4.99 out of 5 average rating, 192 reviews, 1 queen bed, 1 bathroom
9–14 Aug
Top guest favourite
Guest suite in Winchester
Retro Vibe Studio
4.94 out of 5 average rating, 65 reviews, 1 bed, 1 bathroom
12–17 Oct
Guest favourite
Home in Winchester
Historic District Charm On Cameron Street
4.92 out of 5 average rating, 175 reviews, 3 bedrooms, 3 beds, 1.5 bathrooms
10–15 Aug
Guest favourite
Flat in Winchester
Scarborough Fair walk to downtown two story apt
4.9 out of 5 average rating, 142 reviews, 3 bedrooms, 6 beds, 1 bathroom
2–7 Aug
Top guest favourite
Cottage in Berryville
Milton Valley Cottage on Historic Estate Farm
4.97 out of 5 average rating, 119 reviews, 2 bedrooms, 2 beds, 1.5 bathrooms
4–9 Aug
Top guest favourite
Flat in Winchester
Peaceful Family Retreat in the Heart of Winchester
5.0 out of 5 average rating, 76 reviews, 1 bedroom, 3 beds, 1 bathroom
16–21 Aug
Top guest favourite
Home in Winchester
Aunt Tim's Farmhouse
4.96 out of 5 average rating, 159 reviews, 5 bedrooms, 6 beds, 1.5 bathrooms
29 Aug – 3 Sept
Guest favourite
Home in Winchester
Winchester farm
5.0 out of 5 average rating, 13 reviews, 3 bedrooms, 3 beds, 2.5 bathrooms
1–6 Aug
Top guest favourite
Home in Winchester
Skyview Farmhouse
4.98 out of 5 average rating, 55 reviews, 3 bedrooms, 5 beds, 2 bathrooms
1–6 Aug
Superhost
Loft in Winchester
Immerse Yourself in Old Town #3 We'll Pay Parking!
4.72 out of 5 average rating, 75 reviews, 1 bedroom, 2 beds, 1 bathroom
15–22 Aug
Hotel room in Winchester
George Washington l Queen Bed l Historic Charm
5.0 out of 5 average rating, 3 reviews, 1 bedroom, 1 bathroom
1–6 Aug
Guest favourite
Flat in Winchester
Cameron Loft 2 Story Studio with 1.5 Bath Downtown
5.0 out of 5 average rating, 16 reviews, 1 bedroom, 1 bed, 1.5 bathrooms
1–6 Aug
Top guest favourite
Home in Winchester
Bear Drop Inn, walking trails, pond, Winchester
5.0 out of 5 average rating, 24 reviews, 4 bedrooms, 7 beds, 3.5 bathrooms
1–6 Aug