Search results; Over 1,000 places in Winchester

Prices include all fees

Explore more homes

Guest favorite
Home in Winchester
Indigo Blue modern open vibe on tree lined street
3 beds
May 4 – 9
ﺩ.ﺇ5,101 for 5 nights
for 5 nights
4.95 out of 5 average rating, 183 reviews
Apartment in Winchester
Two Bdrm. Flat w/ Patio Terrace
Free cancellation
Jun 15 – 20
ﺩ.ﺇ2,777 for 5 nights
for 5 nights
5.0 out of 5 average rating, 4 reviews
Superhost
Loft in Winchester
Immerse yourself in Old Town Winchester (Apt #4)
Free cancellation
May 11 – 16
ﺩ.ﺇ1,571 for 5 nights
for 5 nights
4.72 out of 5 average rating, 647 reviews
Guest favorite
Apartment in Winchester
Easy like a Sunday Morning 1 BR apt great location
1 bed
May 26 – 31
ﺩ.ﺇ1,761 for 5 nights
for 5 nights
4.97 out of 5 average rating, 66 reviews
Top guest favorite
Apartment in Winchester
Downtowner
Free cancellation
May 11 – 16
ﺩ.ﺇ2,691 for 5 nights
for 5 nights
4.97 out of 5 average rating, 272 reviews
Guest favorite
Room in Winchester
Stay with PepperCustomer care,
Cheerful one bedroom available.
May 22 – 27
ﺩ.ﺇ913 for 5 nights
for 5 nights
4.78 out of 5 average rating, 175 reviews
Guest favorite
Townhouse in Winchester
Modern Elegance in Historic Old Town Winchester
Free cancellation
Jun 21 – 26
ﺩ.ﺇ2,764 for 5 nights
for 5 nights
4.93 out of 5 average rating, 236 reviews
Top guest favorite
Apartment in Winchester
Old Town Loft Modern Oasis In Downtown Winchester
Free cancellation
May 17 – 22
ﺩ.ﺇ4,046 for 5 nights
for 5 nights
4.98 out of 5 average rating, 101 reviews
Guest favorite
Apartment in Winchester
Newly repurposed Historic Home in Winchester VA!
Free cancellation
May 4 – 9
ﺩ.ﺇ2,006 for 5 nights
for 5 nights
4.91 out of 5 average rating, 98 reviews
Top guest favorite
Apartment in Winchester
Old Town Loft In Highly Desirable Area Downtown
Free cancellation
May 31 – Jun 5
ﺩ.ﺇ3,357 for 5 nights
for 5 nights
5.0 out of 5 average rating, 202 reviews
Top guest favorite
Apartment in Winchester
Historic Wisteria House on Old Town Walking Mall
Free cancellation
Jun 9 – 14
ﺩ.ﺇ3,293 for 5 nights
for 5 nights
4.98 out of 5 average rating, 99 reviews
Guest favorite
Guest suite in Winchester
Safe, cozy oasis with private living & bath.
2 beds
May 3 – 8
ﺩ.ﺇ1,711 for 5 nights
for 5 nights
4.81 out of 5 average rating, 331 reviews
Top guest favorite
Home in Winchester
Downtown Chic Condo w/parking
Free cancellation
Jun 7 – 12
ﺩ.ﺇ3,423 for 5 nights
for 5 nights
5.0 out of 5 average rating, 53 reviews
Top guest favorite
Dome in Broadway
Underground Hobbit Style Dome House.
Free cancellation
Aug 4 – 9
ﺩ.ﺇ3,982 for 5 nights
for 5 nights
4.99 out of 5 average rating, 436 reviews
Guest favorite
Yurt in Front Royal
Skyline Yurt: Hot Tub~Wood Stove~WiFi~EVcharger
Free cancellation
May 11 – 16
ﺩ.ﺇ13,194 for 5 nights
for 5 nights
4.98 out of 5 average rating, 131 reviews
Top guest favorite
Campsite in Front Royal
Blue Mountain Hideaway- Unique Glamping Experience
Free cancellation
May 11 – 16
ﺩ.ﺇ3,156 for 5 nights
for 5 nights
4.98 out of 5 average rating, 178 reviews
Superhost
Guest suite in Winchester
Retro Vibe Studio
1 queen bed
May 5 – 10
ﺩ.ﺇ2,067 for 5 nights
for 5 nights
4.93 out of 5 average rating, 55 reviews
Guest favorite
Apartment in Winchester
Scarborough Fair walk to downtown two story apt
6 beds
May 4 – 9
ﺩ.ﺇ5,187 for 5 nights
for 5 nights
4.91 out of 5 average rating, 106 reviews