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Search results; Over 1,000 places in Winchester

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Prices include all fees

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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

Explore more homes

Top guest favorite

Apartment in Winchester

Downtowner

3 beds

May 18 – 23

ﺩ.ﺇ2,691 for 5 nights

for 5 nights

4.97 out of 5 average rating, 274 reviews

Guest favorite

Home in Winchester

Indigo Blue modern open vibe on tree lined street

Free cancellation

Jun 1 – 6

ﺩ.ﺇ5,101 for 5 nights

for 5 nights

4.95 out of 5 average rating, 186 reviews

Superhost

Loft in Winchester

Immerse yourself in Old Town Winchester (Apt #4)

3 beds

May 18 – 23

ﺩ.ﺇ1,532 for 5 nights

for 5 nights

4.72 out of 5 average rating, 649 reviews

Top guest favorite

Apartment in Winchester

Historic Wisteria House on Old Town Walking Mall

Free cancellation

May 30 – Jun 4

ﺩ.ﺇ3,293 for 5 nights

for 5 nights

4.98 out of 5 average rating, 100 reviews

Guest favorite

Apartment in Winchester

Newly repurposed Historic Home in Winchester VA!

1 queen bed

May 19 – 24

ﺩ.ﺇ2,075 for 5 nights

for 5 nights

4.91 out of 5 average rating, 100 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, 203 reviews

Guest favorite

Room in Winchester

Stay with PepperCustomer care,

Cheerful one bedroom available.

May 24 – 29

ﺩ.ﺇ908 for 5 nights

for 5 nights

4.78 out of 5 average rating, 179 reviews

Top guest favorite

Apartment in Winchester

Easy like a Sunday Morning 1 BR apt great location

1 bed

May 26 – 31

ﺩ.ﺇ1,734 for 5 nights

for 5 nights

4.96 out of 5 average rating, 70 reviews

Top guest favorite

Apartment in Winchester

Old Town Loft Modern Oasis In Downtown Winchester

Free cancellation

May 29 – Jun 3

ﺩ.ﺇ3,986 for 5 nights

for 5 nights

4.98 out of 5 average rating, 102 reviews

Apartment in Winchester

Two Bdrm. Flat w/ Patio Terrace

Free cancellation

Jun 15 – 20

ﺩ.ﺇ3,036 for 5 nights

for 5 nights

4.71 out of 5 average rating, 7 reviews

Top guest favorite

Home in Winchester

Cabin in Historic Old Town Winchester

Free cancellation

May 26 – 31

ﺩ.ﺇ3,143 for 5 nights

for 5 nights

4.95 out of 5 average rating, 37 reviews

Guest favorite

Guest suite in Winchester

Safe, cozy oasis with private living & bath.

2 beds

May 19 – 24

ﺩ.ﺇ1,711 for 5 nights

for 5 nights

4.81 out of 5 average rating, 333 reviews

Guest favorite

Townhouse in Winchester

Modern Elegance in Historic Old Town Winchester

Free cancellation

Jun 21 – 26

ﺩ.ﺇ2,785 for 5 nights

for 5 nights

4.93 out of 5 average rating, 239 reviews

Guest favorite

Home in Winchester

Historic District Charm On Cameron Street

Free cancellation

Jul 26 – 31

ﺩ.ﺇ3,444 for 5 nights

for 5 nights

4.94 out of 5 average rating, 153 reviews

Top guest favorite

Cottage in Winchester

Uber SXY Private Country Escape! Hot Tub & Views~

1 queen bed

May 27 – Jun 1

ﺩ.ﺇ5,364 for 5 nights

for 5 nights

4.99 out of 5 average rating, 398 reviews

Superhost

Apartment in Winchester

The Blue Door steps from Handley Library

1 sofa bed

May 17 – 22

ﺩ.ﺇ2,820 for 5 nights

for 5 nights

4.75 out of 5 average rating, 111 reviews

Superhost

Camper/RV in Hedgesville

Explore Creekside RV Bliss #3

Free cancellation

Jun 1 – 6

ﺩ.ﺇ2,712 for 5 nights

for 5 nights

5.0 out of 5 average rating, 4 reviews

Top guest favorite

Room in Winchester

Stay with Holly

Winchester Private Room

May 20 – 25

ﺩ.ﺇ1,184 for 5 nights

for 5 nights

4.98 out of 5 average rating, 107 reviews

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