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
Free cancellation
May 25 – 30
ﺩ.ﺇ 5,101 for 5 nights
for 5 nights
4.95 out of 5 average rating, 184 reviews
Apartment in Winchester
Two Bdrm. Flat w/ Patio Terrace
Free cancellation
Jun 15 – 20
ﺩ.ﺇ 3,036 for 5 nights
for 5 nights
5.0 out of 5 average rating, 4 reviews
Top guest favorite
Apartment in Winchester
Historic Wisteria House on Old Town Walking Mall
1 queen bed
May 8 – 13
ﺩ.ﺇ 3,293 for 5 nights
for 5 nights
4.98 out of 5 average rating, 99 reviews
Top guest favorite
Apartment in Winchester
Downtowner
3 beds
May 11 – 16
ﺩ.ﺇ 2,691 for 5 nights
for 5 nights
4.97 out of 5 average rating, 273 reviews
Top guest favorite
Apartment in Winchester
Old Town Loft Modern Oasis In Downtown Winchester
Free cancellation
May 17 – 22
ﺩ.ﺇ 3,710 for 5 nights
for 5 nights
4.98 out of 5 average rating, 102 reviews
Top guest favorite
Apartment in Winchester
Easy like a Sunday Morning 1 BR apt great location
1 bed
May 10 – 15
ﺩ.ﺇ 1,737 for 5 nights
for 5 nights
4.97 out of 5 average rating, 67 reviews
Guest favorite
Room in Winchester
Stay with PepperCustomer care,
Cheerful one bedroom available.
May 22 – 27
ﺩ.ﺇ 917 for 5 nights
for 5 nights
4.78 out of 5 average rating, 176 reviews
Superhost
Loft in Winchester
Immerse yourself in Old Town Winchester (Apt #4)
3 beds
May 11 – 16
ﺩ.ﺇ 1,593 for 5 nights
for 5 nights
4.72 out of 5 average rating, 648 reviews
Top guest favorite
Apartment in Winchester
Old Town Loft In Highly Desirable Area Downtown
Free cancellation
May 31 – Jun 5
ﺩ.ﺇ 3,357 for 5 nights
for 5 nights
5.0 out of 5 average rating, 202 reviews
Guest favorite
Apartment in Winchester
Newly repurposed Historic Home in Winchester VA!
Free cancellation
May 11 – 16
ﺩ.ﺇ 2,006 for 5 nights
for 5 nights
4.91 out of 5 average rating, 99 reviews
Guest favorite
Guest suite in Winchester
Safe, cozy oasis with private living & bath.
2 beds
May 5 – 10
ﺩ.ﺇ 1,872 for 5 nights
for 5 nights
4.81 out of 5 average rating, 332 reviews
Guest favorite
Townhouse in Winchester
Modern Elegance in Historic Old Town Winchester
Free cancellation
Jun 21 – 26
ﺩ.ﺇ 2,764 for 5 nights
for 5 nights
4.93 out of 5 average rating, 236 reviews
Top guest favorite
Apartment in Winchester
Downtown FUN! Personal Mid Century 2bd Apartment!
2 queen beds
May 26 – 31
ﺩ.ﺇ 2,544 for 5 nights
for 5 nights
4.89 out of 5 average rating, 217 reviews
Guest favorite
Apartment in Winchester
Scarborough Fair walk to downtown two story apt
6 beds
May 5 – 10
ﺩ.ﺇ 5,274 for 5 nights
for 5 nights
4.91 out of 5 average rating, 106 reviews
Top guest favorite
Room in Winchester
Stay with Holly
Winchester Private Room
May 10 – 15
ﺩ.ﺇ 1,184 for 5 nights
for 5 nights
4.98 out of 5 average rating, 105 reviews
Superhost
Apartment in Winchester
Cleveland Park bright 2BR apt blocks from downtown
2 queen beds
May 5 – 10
ﺩ.ﺇ 3,926 for 5 nights
for 5 nights
4.76 out of 5 average rating, 88 reviews
Top guest favorite
Home in Winchester
Aunt Tim's Farmhouse
6 beds
May 5 – 10
ﺩ.ﺇ 3,766 for 5 nights
for 5 nights
4.96 out of 5 average rating, 124 reviews
Guest favorite
Home in Winchester
Cozy Cottage
Free cancellation
Jun 16 – 21
ﺩ.ﺇ 2,045 for 5 nights
for 5 nights
4.91 out of 5 average rating, 260 reviews