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Search results; Over 1,000 places in Winchester

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Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Explore more homes

Guest favorite

Apartment in Winchester

Newly repurposed Historic Home in Winchester VA!

1 queen bed

Jun 1 – 6

ﺩ.ﺇ2,006 for 5 nights

for 5 nights

4.91 out of 5 average rating, 102 reviews

Guest favorite

Townhouse in Winchester

Brewhouse renovated row house steps from downtown

3 beds

Jun 1 – 6

ﺩ.ﺇ4,132 for 5 nights

for 5 nights

4.94 out of 5 average rating, 82 reviews

Guest favorite

Apartment in Winchester

Downtowner

Free cancellation

Jun 22 – 27

ﺩ.ﺇ2,691 for 5 nights

for 5 nights

4.97 out of 5 average rating, 277 reviews

Guest favorite

Townhouse in Winchester

Modern Elegance in Historic Old Town Winchester

Free cancellation

Jun 21 – 26

ﺩ.ﺇ2,772 for 5 nights

for 5 nights

4.93 out of 5 average rating, 241 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, 109 reviews

Top guest favorite

Apartment in Winchester

Old Town Loft Modern Oasis In Downtown Winchester

2 beds

Jun 1 – 6

ﺩ.ﺇ3,357 for 5 nights

for 5 nights

4.98 out of 5 average rating, 105 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, 188 reviews

Top guest favorite

Apartment in Winchester

Historic Wisteria House on Old Town Walking Mall

Free cancellation

Jun 23 – 28

ﺩ.ﺇ3,314 for 5 nights

for 5 nights

4.98 out of 5 average rating, 100 reviews

Superhost

Room in Winchester

Stay with J ArmandoAirport,

Private Room in Winchester VA

Jun 1 – 6

ﺩ.ﺇ1,098 for 5 nights

for 5 nights

4.33 out of 5 average rating, 3 reviews

Room in Stephens City

Stay with Racquel

Comfy 2BR | Work, Relax, Explore

Jun 1 – 6

ﺩ.ﺇ1,756 for 5 nights

for 5 nights

New place to stay

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, 204 reviews

Top guest favorite

Home in Winchester

Colonial Getaway Near Old Town Historic Winchester

Free cancellation

Jun 15 – 20

ﺩ.ﺇ3,354 for 5 nights

for 5 nights

4.97 out of 5 average rating, 196 reviews

Top guest favorite

Home in Winchester

Downtown Chic Condo w/parking

Free cancellation

Jun 27 – Jul 2

ﺩ.ﺇ3,793 for 5 nights

for 5 nights

5.0 out of 5 average rating, 55 reviews

Guest favorite

Room in Stephens City

Stay with Clara

Twin Room in Quiet Neighborhood

Jun 8 – 13

ﺩ.ﺇ969 for 5 nights

for 5 nights

4.87 out of 5 average rating, 23 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, 39 reviews

Guest favorite

Room in Winchester

Stay with PepperCustomer care,

Cheerful one bedroom available.

Aug 16 – 21

ﺩ.ﺇ990 for 5 nights

for 5 nights

4.77 out of 5 average rating, 183 reviews

Guest favorite

Cottage in Front Royal

Riverfront Paradise | Hot Tub | Sauna | FirePit

3 king beds

Jun 1 – 6

ﺩ.ﺇ7,139 for 5 nights

for 5 nights

5.0 out of 5 average rating, 13 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, 45 reviews

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