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Search results; Over 1,000 homes in Winchester

Top guest favourite
Cottage in Winchester
COZY+SEXY Private Country Escape! HOT TUB & Views~
1 bedroom, 1 bed, 1 private bathroom
16–21 Aug
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4.99 out of 5 average rating, 481 reviews
Top guest favourite
Flat in Winchester
Downtowner
2 bedrooms, 3 beds, 1 bathroom
2–7 Aug
4.97 out of 5 average rating, 354 reviews
Top guest favourite
Flat in Winchester
Old Town Modern Twist! Rock n’ Roll FUN w/Parking!
2 bedrooms, 2 beds, 1 bathroom
15–20 Aug
4.95 out of 5 average rating, 203 reviews
Top guest favourite
Home in Winchester
Cameron Charmer pristine w/double master suites
2 bedrooms, 2 queen beds, 2.5 bathrooms
2–7 Aug
4.98 out of 5 average rating, 221 reviews
Top guest favourite
Room in Winchester
Winchester Private Room
1 queen bed, 1 bathroom
9–14 Aug
4.99 out of 5 average rating, 192 reviews
Top guest favourite
Home in Winchester
Colonial Getaway Near Old Town Historic Winchester
3 bedrooms, 4 beds, 2.5 bathrooms
4–9 Sept
4.98 out of 5 average rating, 246 reviews
Top guest favourite
Guest suite in Winchester
Retro Vibe Studio
1 queen bed, 1 bathroom
12–17 Oct
4.94 out of 5 average rating, 65 reviews
Guest favourite
Home in Winchester
Historic District Charm On Cameron Street
3 bedrooms, 3 beds, 1.5 bathrooms
10–15 Aug
4.92 out of 5 average rating, 175 reviews
Guest favourite
Flat in Winchester
Scarborough Fair walk to downtown two story apt
3 bedrooms, 6 beds, 1 bathroom
2–7 Aug
4.9 out of 5 average rating, 142 reviews
Top guest favourite
Home in Winchester
Aunt Tim's Farmhouse
5 bedrooms, 6 beds, 1.5 bathrooms
29 Aug – 3 Sept
4.96 out of 5 average rating, 159 reviews
Top guest favourite
Cottage in Berryville
Milton Valley Cottage on Historic Estate Farm
2 bedrooms, 2 beds, 1.5 bathrooms
4–9 Aug
4.97 out of 5 average rating, 119 reviews
Top guest favourite
Flat in Winchester
Peaceful Family Retreat in the Heart of Winchester
1 bedroom, 3 beds, 1 bathroom
16–21 Aug
5.0 out of 5 average rating, 76 reviews
Top guest favourite
Home in Winchester
Springdale Mill Farmhouse with Spa House
4 bedrooms, 5 beds, 2.5 bathrooms
1–6 Aug
4.87 out of 5 average rating, 91 reviews
Top guest favourite
Home in Warren County
Mountain Views w/Hot Tub, 95” TV & Trail Access
3 bedrooms, 4 beds, 3.5 bathrooms
16–21 Aug
5.0 out of 5 average rating, 6 reviews
Guest favourite
Flat in Winchester
Cameron Loft 2 Story Studio with 1.5 Bath Downtown
1 bedroom, 1 double bed, 1.5 bathrooms
1–6 Aug
5.0 out of 5 average rating, 16 reviews
Top guest favourite
Home in Winchester
Misty Meadow has quite setting in the country.
2 bedrooms, 2 beds, 1.5 bathrooms
8–13 Aug
4.93 out of 5 average rating, 90 reviews
Top guest favourite
Home in Winchester
Large Historic Stone Home in the Heart of Old Town
4 bedrooms, 4 beds, 3 bathrooms
10–15 Aug
5.0 out of 5 average rating, 77 reviews
Superhost
Loft in Winchester
Immerse Yourself in Old Town #3 We'll Pay Parking!
1 bedroom, 2 beds, 1 bathroom
30 Aug – 6 Sept
4.72 out of 5 average rating, 75 reviews
Hotel room in Winchester
George Washington l Queen Bed l Historic Charm
1 bedroom, 1 queen bed, 1 bathroom
1–6 Aug
5.0 out of 5 average rating, 3 reviews