Search results; Over 1,000 places in Winchester

Prices include all fees

Explore more homes

Top guest favorite
Apartment in Winchester
Old Town Loft Modern Oasis In Downtown Winchester
Free cancellation
Jun 1 – 6
ﺩ.ﺇ3,357 for 5 nights
for 5 nights
4.98 out of 5 average rating, 103 reviews
Guest favorite
Home in Winchester
Indigo Blue modern open vibe on tree lined street
Free cancellation
Jun 15 – 20
ﺩ.ﺇ5,101 for 5 nights
for 5 nights
4.95 out of 5 average rating, 186 reviews
Guest favorite
Apartment in Winchester
Downtowner
Free cancellation
Jun 11 – 16
ﺩ.ﺇ2,777 for 5 nights
for 5 nights
4.97 out of 5 average rating, 276 reviews
Guest favorite
Apartment in Winchester
Newly repurposed Historic Home in Winchester VA!
Free cancellation
Jun 1 – 6
ﺩ.ﺇ2,006 for 5 nights
for 5 nights
4.91 out of 5 average rating, 101 reviews
Top guest favorite
Room in Winchester
Stay with Holly
Winchester Private Room
Jun 15 – 20
ﺩ.ﺇ1,184 for 5 nights
for 5 nights
4.98 out of 5 average rating, 108 reviews
Guest favorite
Townhouse in Winchester
Modern Elegance in Historic Old Town Winchester
Free cancellation
Jun 21 – 26
ﺩ.ﺇ2,782 for 5 nights
for 5 nights
4.93 out of 5 average rating, 239 reviews
Superhost
Loft in Winchester
Immerse yourself in Old Town Winchester (Apt #4)
Free cancellation
Jul 11 – 16
ﺩ.ﺇ1,743 for 5 nights
for 5 nights
4.72 out of 5 average rating, 650 reviews
Top guest favorite
Apartment in Winchester
Historic Wisteria House on Old Town Walking Mall
Free cancellation
Jun 23 – 28
ﺩ.ﺇ3,310 for 5 nights
for 5 nights
4.98 out of 5 average rating, 100 reviews
Top guest favorite
Home in Winchester
Cabin in Historic Old Town Winchester
Free cancellation
Jun 9 – 14
ﺩ.ﺇ3,143 for 5 nights
for 5 nights
4.95 out of 5 average rating, 38 reviews
Top guest favorite
Apartment in Winchester
Easy like a Sunday Morning 1 BR apt great location
1 bed
Jun 1 – 6
ﺩ.ﺇ1,734 for 5 nights
for 5 nights
4.96 out of 5 average rating, 72 reviews
Top guest favorite
Home in Winchester
Downtown Chic Condo w/parking
Free cancellation
Jun 27 – Jul 2
ﺩ.ﺇ3,814 for 5 nights
for 5 nights
5.0 out of 5 average rating, 55 reviews
Top guest favorite
Apartment in Winchester
Peaceful Family Retreat in the Heart of Winchester
Free cancellation
Jun 9 – 14
ﺩ.ﺇ2,002 for 5 nights
for 5 nights
5.0 out of 5 average rating, 44 reviews
Top guest favorite
Apartment in Winchester
Old Town Loft In Highly Desirable Area Downtown
Free cancellation
Jun 21 – 26
ﺩ.ﺇ3,357 for 5 nights
for 5 nights
5.0 out of 5 average rating, 203 reviews
Apartment in Winchester
Two Bdrm. Flat w/ Patio Terrace
Free cancellation
Jun 14 – 19
ﺩ.ﺇ3,036 for 5 nights
for 5 nights
4.75 out of 5 average rating, 8 reviews
Guest favorite
Cabin in Front Royal
The Wizard's Chalet • Cozy nature escape • Hot Tub
Free cancellation
Jun 1 – 6
ﺩ.ﺇ5,037 for 5 nights
for 5 nights
4.95 out of 5 average rating, 208 reviews
Guest favorite
Townhouse in Winchester
Brewhouse renovated row house steps from downtown
Free cancellation
Jun 1 – 6
ﺩ.ﺇ4,132 for 5 nights
for 5 nights
4.95 out of 5 average rating, 81 reviews
Superhost
Room in Winchester
Stay with J ArmandoAirport,
Studio Apartment in Winchester
Jun 1 – 6
ﺩ.ﺇ1,335 for 5 nights
for 5 nights
4.88 out of 5 average rating, 8 reviews
Room in Winchester
Stay with MistyMissionary to africa,
Peaceful home near hospital
Jun 8 – 13
ﺩ.ﺇ1,400 for 5 nights
for 5 nights