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
26–31 Jul
,
4.99 out of 5 average rating, 479 reviews
Top guest favourite
Flat in Winchester
Downtowner
3 beds
2–7 Aug
4.97 out of 5 average rating, 351 reviews
Top guest favourite
Room in Winchester
Stay with Holly
Winchester Private Room
19–24 Jul
4.99 out of 5 average rating, 189 reviews
Top guest favourite
Flat in Winchester
Downtown FUN! Personal Mid Century 2bd Apartment!
2 queen beds
19–24 Jul
4.9 out of 5 average rating, 271 reviews
Top guest favourite
Home in Winchester
Skyview Farmhouse
5 beds
14–19 Jul
4.98 out of 5 average rating, 54 reviews
Top guest favourite
Home in Winchester
Aunt Tim's Farmhouse
6 beds
26–31 Jul
4.96 out of 5 average rating, 158 reviews
Guest favourite
Flat in Winchester
Scarborough Fair walk to downtown two story apt
6 beds
19–24 Jul
4.9 out of 5 average rating, 140 reviews
Top guest favourite
Home in Winchester
Colonial Getaway Near Old Town Historic Winchester
4 beds
1–6 Aug
4.98 out of 5 average rating, 244 reviews
Superhost
Cabin in Great Cacapon
New Listing! Riverfront Home w/ Hot Tub & Fire Pit
2 beds
16–21 Aug
5.0 out of 5 average rating, 4 reviews
Guest favourite
Cabin in Strasburg
The Haven at Turkey Run • Hot Tub, Fire Pit, Games
3 king beds
26–31 Jul
4.95 out of 5 average rating, 85 reviews
Top guest favourite
Home in Clear Brook
Cedar Hill Cottage- 3 mi to I-81 & Rt 11
2 queen beds
9–14 Aug
4.94 out of 5 average rating, 52 reviews
Top guest favourite
Flat in Winchester
Historic French Modern Downtown
2 beds
14–19 Jul
4.95 out of 5 average rating, 39 reviews
Cabin in Winchester
Private Mountain Retreat | Sauna, Hot Tub & Views
2 beds
19–24 Jul
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Clear Brook
Sunrise/Sunset Views
5 beds
21–26 Jul
5.0 out of 5 average rating, 10 reviews
Top guest favourite
Guest suite in Winchester
Retro Vibe Studio
1 queen bed
26–31 Jul
4.94 out of 5 average rating, 63 reviews
Top guest favourite
Cottage in Winchester
Emma's Stone Cottage
3 beds
25–30 Jul
4.98 out of 5 average rating, 571 reviews
Guest favourite
Flat in Winchester
Two Bdrm. Flat w/ Patio Terrace
2 beds
21–28 Jul
4.88 out of 5 average rating, 25 reviews
Guest favourite
Home in Millwood
Peony Place renovated farmhouse in horse country
2 beds
27 Jul – 1 Aug
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Home in Winchester
Cameron Charmer pristine w/double master suites
2 queen beds
2–7 Aug
4.98 out of 5 average rating, 221 reviews