Search results; Over 1,000 places in Winchester

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Top guest favorite
Room in Winchester
Stay with Holly
Winchester Private Room
Jun 15 – 20
R5,880 ZAR for 5 nights
for 5 nights
4.98 out of 5 average rating, 109 reviews
Guest favorite
Apartment in Winchester
Newly repurposed Historic Home in Winchester VA!
1 queen bed
Jun 1 – 6
R9,964 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
R13,365 ZAR 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
R13,770 ZAR for 5 nights
for 5 nights
4.93 out of 5 average rating, 241 reviews
Guest favorite
Townhouse in Winchester
Brewhouse renovated row house steps from downtown
3 beds
Jun 1 – 6
R20,527 ZAR for 5 nights
for 5 nights
4.94 out of 5 average rating, 82 reviews
Top guest favorite
Apartment in Winchester
Historic Wisteria House on Old Town Walking Mall
Free cancellation
Jun 23 – 28
R16,358 ZAR for 5 nights
for 5 nights
4.98 out of 5 average rating, 100 reviews
Guest favorite
Room in Winchester
Stay with PepperCustomer care,
Cheerful one bedroom available.
Aug 16 – 21
R4,918 ZAR for 5 nights
for 5 nights
4.77 out of 5 average rating, 183 reviews
Top guest favorite
Apartment in Winchester
Old Town Loft Modern Oasis In Downtown Winchester
2 beds
Jun 1 – 6
R16,678 ZAR 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
R25,339 ZAR for 5 nights
for 5 nights
4.95 out of 5 average rating, 188 reviews
Top guest favorite
Home in Winchester
Cameron Charmer pristine w/double master suites
Free cancellation
Jul 13 – 18
R20,741 ZAR for 5 nights
for 5 nights
4.97 out of 5 average rating, 196 reviews
Room in Stephens City
Stay with Racquel
Comfy 2BR | Work, Relax, Explore
Jun 1 – 6
R8,724 ZAR for 5 nights
for 5 nights
New place to stay
Top guest favorite
Home in Winchester
Colonial Getaway Near Old Town Historic Winchester
Free cancellation
Jun 15 – 20
R16,657 ZAR for 5 nights
for 5 nights
4.97 out of 5 average rating, 196 reviews
Superhost
Room in Winchester
Stay with J ArmandoAirport,
Private room in Winchester VA
Jun 1 – 6
R5,453 ZAR for 5 nights
for 5 nights
4.73 out of 5 average rating, 11 reviews
Superhost
Loft in Winchester
Immerse yourself in Old Town Winchester (Apt #4)
Free cancellation
Jul 11 – 16
R8,574 ZAR for 5 nights
for 5 nights
4.72 out of 5 average rating, 654 reviews
Top guest favorite
Apartment in Winchester
Peaceful Family Retreat in the Heart of Winchester
Free cancellation
Jun 9 – 14
R9,944 ZAR for 5 nights
for 5 nights
5.0 out of 5 average rating, 45 reviews
Top guest favorite
Room in Stephens City
Stay with Clara
Room in Quiet Neighborhood
Jun 9 – 14
R5,089 ZAR for 5 nights
for 5 nights
5.0 out of 5 average rating, 32 reviews
Superhost
Apartment in Winchester
Cleveland Park bright 2BR apt blocks from downtown
2 queen beds
Jun 1 – 6
R19,138 ZAR for 5 nights
for 5 nights
4.75 out of 5 average rating, 91 reviews
Top guest favorite
Apartment in Winchester
Old Town Loft In Highly Desirable Area Downtown
Free cancellation
Jun 21 – 26
R16,678 ZAR for 5 nights
for 5 nights
5.0 out of 5 average rating, 204 reviews