Search results; Over 1,000 places in Winchester

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Guest favorite
Townhouse in Winchester
Modern Elegance in Historic Old Town Winchester
Free cancellation
Jun 21 – 26
R13,517 ZAR 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 8 – 13
R5,790 ZAR for 5 nights
for 5 nights
4.98 out of 5 average rating, 110 reviews
Top guest favorite
Apartment in Winchester
Old Town Loft In Highly Desirable Area Downtown
Free cancellation
Jun 21 – 26
R16,421 ZAR for 5 nights
for 5 nights
5.0 out of 5 average rating, 205 reviews
Top guest favorite
Apartment in Winchester
Historic Wisteria House on Old Town Walking Mall
Free cancellation
Jun 23 – 28
R16,106 ZAR 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
Jun 8 – 13
R9,811 ZAR for 5 nights
for 5 nights
4.91 out of 5 average rating, 102 reviews
Guest favorite
Apartment in Winchester
Downtowner
Free cancellation
Jun 22 – 27
R13,159 ZAR for 5 nights
for 5 nights
4.97 out of 5 average rating, 279 reviews
Guest favorite
Home in Winchester
Indigo Blue modern open vibe on tree lined street
Free cancellation
Jun 15 – 20
R24,949 ZAR for 5 nights
for 5 nights
4.95 out of 5 average rating, 188 reviews
Guest favorite
Room in Winchester
Stay with PepperCustomer care,
Cheerful one bedroom available.
Aug 16 – 21
R4,884 ZAR for 5 nights
for 5 nights
4.76 out of 5 average rating, 187 reviews
Top guest favorite
Home in Winchester
Aunt Tim's Farmhouse
Free cancellation
Jun 15 – 20
R18,422 ZAR for 5 nights
for 5 nights
4.96 out of 5 average rating, 128 reviews
Superhost
Loft in Winchester
Immerse yourself in Old Town Winchester (Apt #4)
Free cancellation
Jul 11 – 16
R8,526 ZAR for 5 nights
for 5 nights
4.73 out of 5 average rating, 655 reviews
Guest favorite
Home in Winchester
Historic District Charm On Cameron Street
Free cancellation
Jul 26 – 31
R16,843 ZAR for 5 nights
for 5 nights
4.94 out of 5 average rating, 154 reviews
Top guest favorite
Apartment in Winchester
Old Town Loft Modern Oasis In Downtown Winchester
Free cancellation
Jul 14 – 19
R19,790 ZAR for 5 nights
for 5 nights
4.98 out of 5 average rating, 105 reviews
Superhost
Apartment in Winchester
Downtown 1920's Gas Station with Hot Tub
1 queen bed
Jun 8 – 13
R13,948 ZAR for 5 nights
for 5 nights
4.9 out of 5 average rating, 350 reviews
Top guest favorite
Home in Winchester
Cabin in Historic Old Town Winchester
Free cancellation
Jun 23 – 28
R15,369 ZAR for 5 nights
for 5 nights
4.95 out of 5 average rating, 39 reviews
Top guest favorite
Apartment in Winchester
Downtown FUN! Personal Mid Century 2bd Apartment!
2 queen beds
Jul 18 – 23
R12,365 ZAR for 5 nights
for 5 nights
4.89 out of 5 average rating, 221 reviews
Superhost
Apartment in Winchester
"Cozy on Cameron!" - Historic Downtown Winchester
1 queen bed
Jun 10 – 15
R12,000 ZAR for 5 nights
for 5 nights
4.83 out of 5 average rating, 12 reviews
Top guest favorite
Home in Winchester
Whole 3-bedroom house walkable to downtown.
Free cancellation
Aug 2 – 7
R17,053 ZAR for 5 nights
for 5 nights
5.0 out of 5 average rating, 33 reviews
Home in Winchester
Apartment/Great Private floor
2 beds
Jun 8 – 13
R15,159 ZAR for 5 nights
for 5 nights
4.75 out of 5 average rating, 4 reviews