Search results; Over 1,000 places in Winchester

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Superhost
Loft in Winchester
Immerse yourself in Old Town Winchester (Apt #4)
Free cancellation
Jul 11 – 16
R8,628 ZAR for 5 nights
for 5 nights
4.72 out of 5 average rating, 649 reviews
Guest favorite
Apartment in Winchester
Newly repurposed Historic Home in Winchester VA!
Free cancellation
Jun 1 – 6
R9,978 ZAR for 5 nights
for 5 nights
4.91 out of 5 average rating, 101 reviews
Top guest favorite
Apartment in Winchester
Downtowner
Free cancellation
Jun 11 – 16
R13,809 ZAR for 5 nights
for 5 nights
4.97 out of 5 average rating, 276 reviews
Top guest favorite
Room in Winchester
Stay with Holly
Winchester Private Room
Jun 15 – 20
R5,888 ZAR for 5 nights
for 5 nights
4.98 out of 5 average rating, 108 reviews
Top guest favorite
Apartment in Winchester
Old Town Loft Modern Oasis In Downtown Winchester
Free cancellation
Jun 1 – 6
R16,700 ZAR 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 1 – 6
R25,372 ZAR for 5 nights
for 5 nights
4.95 out of 5 average rating, 186 reviews
Guest favorite
Townhouse in Winchester
Modern Elegance in Historic Old Town Winchester
Free cancellation
Jun 21 – 26
R13,832 ZAR for 5 nights
for 5 nights
4.93 out of 5 average rating, 239 reviews
Top guest favorite
Apartment in Winchester
Historic Wisteria House on Old Town Walking Mall
Free cancellation
Jun 23 – 28
R16,423 ZAR for 5 nights
for 5 nights
4.98 out of 5 average rating, 100 reviews
Apartment in Winchester
Two Bdrm. Flat w/ Patio Terrace
Free cancellation
Jun 14 – 19
R15,095 ZAR for 5 nights
for 5 nights
4.75 out of 5 average rating, 8 reviews
Top guest favorite
Home in Winchester
Cameron Charmer pristine w/double master suites
Free cancellation
Jul 13 – 18
R20,768 ZAR for 5 nights
for 5 nights
4.97 out of 5 average rating, 196 reviews
Top guest favorite
Apartment in Winchester
Old Town Loft In Highly Desirable Area Downtown
Free cancellation
Jun 12 – 17
R17,343 ZAR for 5 nights
for 5 nights
5.0 out of 5 average rating, 203 reviews
Guest favorite
Room in Stephens City
Stay with Clara
Twin Room in Quiet Neighborhood
Jun 1 – 6
R4,817 ZAR 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
R15,630 ZAR for 5 nights
for 5 nights
4.95 out of 5 average rating, 38 reviews
Superhost
Apartment in Winchester
Cleveland Park bright 2BR apt blocks from downtown
Free cancellation
Jun 1 – 6
R19,163 ZAR for 5 nights
for 5 nights
4.74 out of 5 average rating, 90 reviews
Top guest favorite
Home in Winchester
Colonial Getaway Near Old Town Historic Winchester
Free cancellation
Jun 15 – 20
R16,680 ZAR for 5 nights
for 5 nights
4.97 out of 5 average rating, 195 reviews
Superhost
Apartment in Winchester
"Cozy on Cameron!" - Historic Downtown Winchester
Free cancellation
Jun 10 – 15
R12,205 ZAR for 5 nights
for 5 nights
4.82 out of 5 average rating, 11 reviews
Guest favorite
Guest suite in Stephens City
Cozy Cabin
Free cancellation
Jun 1 – 6
R9,849 ZAR for 5 nights
for 5 nights
4.94 out of 5 average rating, 88 reviews
Guest favorite
Apartment in Winchester
Yellow Submarine trendy basement apt w/courtyard
Free cancellation
Jun 1 – 6
R20,447 ZAR for 5 nights
for 5 nights
4.79 out of 5 average rating, 119 reviews