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Search results; Over 1,000 homes in Winchester

Descriptions are based on details hosts provide
Top guest favourite
Cottage in Winchester
COZY+SEXY Private Country Escape! HOT TUB & Views~
1 bedroom, 1 bed, 1 private bathroom
26–31 Jul
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4.99 out of 5 average rating, 479 reviews
Top guest favourite
Flat in Winchester
Downtowner
2 bedrooms, 3 beds, 1 bathroom
2–7 Aug
4.97 out of 5 average rating, 352 reviews
Top guest favourite
Room in Winchester
5 minutes from historic downtown Winchester
1 queen bed, 1 bathroom
19–24 Jul
4.99 out of 5 average rating, 189 reviews
Top guest favourite
Home in Winchester
Colonial home near Old Town Winchester
3 bedrooms, 4 beds, 2.5 bathrooms
1–6 Aug
4.98 out of 5 average rating, 245 reviews
Top guest favourite
Home in Winchester
Farmhouse with views near 3 wineries
3 bedrooms, 5 beds, 2 bathrooms
15–20 Jul
4.98 out of 5 average rating, 55 reviews
Top guest favourite
Home in Winchester
Farmhouse on 106 acres near Winchester
5 bedrooms, 6 beds, 1.5 bathrooms
26–31 Jul
4.96 out of 5 average rating, 158 reviews
Guest favourite
Flat in Winchester
Three porches and a walkable downtown
3 bedrooms, 6 beds, 1 bathroom
19–24 Jul
4.9 out of 5 average rating, 140 reviews
Top guest favourite
Home in Clear Brook
Sunrise/Sunset Views
4 bedrooms, 5 beds, 2.5 bathrooms
22–27 Jul
5.0 out of 5 average rating, 10 reviews
Top guest favourite
Flat in Winchester
Mid-century design, one block from downtown
2 bedrooms, 2 queen beds, 1 bathroom
19–24 Jul
4.9 out of 5 average rating, 271 reviews
Top guest favourite
Home in Winchester
Large Historic Stone Home in the Heart of Old Town
4 bedrooms, 4 beds, 3 bathrooms
26–31 Jul
5.0 out of 5 average rating, 76 reviews
Guest favourite
Flat in Winchester
Two Bdrm. Flat w/ Patio Terrace
2 bedrooms, 2 beds, 2 bathrooms
16–23 Sept
4.88 out of 5 average rating, 25 reviews
Top guest favourite
Guest suite in Winchester
Retro Vibe Studio
1 queen bed, 1 bathroom
26–31 Jul
4.94 out of 5 average rating, 63 reviews
Guest favourite
Flat in Winchester
Cameron Loft 2 Story Studio with 1.5 Bath Downtown
1 bedroom, 1 double bed, 1.5 bathrooms
28 Jul – 2 Aug
5.0 out of 5 average rating, 16 reviews
Guest favourite
Home in Winchester
Historic gem with a basketball court
3 bedrooms, 3 beds, 1.5 bathrooms
10–15 Aug
4.92 out of 5 average rating, 175 reviews
Top guest favourite
Home in Clear Brook
Quiet single-level home with a fire pit
2 bedrooms, 2 queen beds, 1.5 bathrooms
9–14 Aug
4.94 out of 5 average rating, 53 reviews
Top guest favourite
Flat in Winchester
Historic French Modern Downtown
2 bedrooms, 2 beds, 1 bathroom
15–20 Jul
4.95 out of 5 average rating, 39 reviews
Top guest favourite
Home in Winchester
Springdale Mill Farmhouse with Spa House
4 bedrooms, 5 beds, 2.5 bathrooms
28 Jul – 2 Aug
4.87 out of 5 average rating, 91 reviews
Top guest favourite
Home in Winchester
6-acre waterfront ranch on Back Creek
3 bedrooms, 3 beds, 3 bathrooms
8–13 Sept
4.91 out of 5 average rating, 47 reviews
Top guest favourite
Cabin in Gerrardstown
The Nest: Modern Cabin Retreat on 5 Wooded Acres
2 bedrooms, 3 beds, 1.5 bathrooms
3–8 Aug
4.98 out of 5 average rating, 202 reviews