Search results; Over 1,000 places in Winchester

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Top guest favorite
Room in Winchester
Stay with Holly
Winchester Private Room
Jul 25 – 30
R5,861 ZAR for 5 nights
4.98 out of 5 average rating, 118 reviews
Guest favorite
Home in Winchester
Cozy Cottage
1 queen bed
Jul 14 – 19
R10,123 ZAR for 5 nights
4.91 out of 5 average rating, 272 reviews
Guest favorite
Townhouse in Winchester
Modern Elegance in Historic Old Town Winchester
Free cancellation
Aug 6 – 11
R14,151 ZAR for 5 nights
4.93 out of 5 average rating, 247 reviews
Top guest favorite
Room in Martinsburg
Stay with ChristyMotorcycle coach,
Wild & Wonderful -built in 1890
Jul 13 – 18
R5,275 ZAR for 5 nights
5.0 out of 5 average rating, 18 reviews
Room in Stephens City
Stay with Racquel
Comfy 2BR | Work, Relax, Explore
Jul 13 – 18
R8,695 ZAR for 5 nights
New place to stay
Top guest favorite
Home in Winchester
Colonial Getaway Near Old Town Historic Winchester
Free cancellation
Aug 1 – 6
R17,454 ZAR for 5 nights
4.97 out of 5 average rating, 204 reviews
Top guest favorite
Room in Stephens City
Stay with Racquel
Comfy 1BR | Work, Relax, Explore
Jul 13 – 18
R7,140 ZAR for 5 nights
5.0 out of 5 average rating, 7 reviews
Top guest favorite
Home in Winchester
City Charmer minutes from Old Town
Free cancellation
Aug 16 – 21
R12,276 ZAR for 5 nights
4.97 out of 5 average rating, 256 reviews
Top guest favorite
Apartment in Winchester
Easy like a Sunday Morning 1 BR apt great location
1 bed
Aug 4 – 9
R8,732 ZAR for 5 nights
4.95 out of 5 average rating, 77 reviews
Top guest favorite
Farm stay in Strasburg
Homestead with Shenandoah Valley Views
1 queen bed
Jul 12 – 17
R11,040 ZAR for 5 nights
4.99 out of 5 average rating, 81 reviews
Superhost
Loft in Winchester
Immerse yourself in Old Town #2 We'll Pay Parking!
Free cancellation
Jul 27 – Aug 3
R10,799 ZAR for 7 nights
4.64 out of 5 average rating, 96 reviews
Guest favorite
Home in Inwood
Arden House, Inwood WV
3 beds
Jul 13 – 18
R7,992 ZAR for 5 nights
4.88 out of 5 average rating, 659 reviews
Guest favorite
Room in Winchester
Stay with PepperCustomer care,
Cheerful one bedroom available.
Aug 2 – 7
R5,520 ZAR for 5 nights
4.77 out of 5 average rating, 188 reviews
Guest favorite
Home in Winchester
Skyview Farmhouse
5 beds
Jul 13 – 18
R24,722 ZAR for 5 nights
4.93 out of 5 average rating, 14 reviews
Top guest favorite
Room in Stephens City
Stay with Clara
Room in Quiet Neighborhood
Aug 1 – 6
R5,136 ZAR for 5 nights
4.97 out of 5 average rating, 35 reviews
Top guest favorite
Apartment in Winchester
Old Town Loft In Highly Desirable Area Downtown
Free cancellation
Jul 20 – 25
R13,826 ZAR for 5 nights
5.0 out of 5 average rating, 211 reviews
Guest favorite
Apartment in Winchester
Newly repurposed Historic Home in Winchester VA!
Free cancellation
Jul 17 – 22
R10,358 ZAR for 5 nights
4.92 out of 5 average rating, 108 reviews
Top guest favorite
Home in Winchester
Misty Meadow has quite setting in the country.
Free cancellation
Aug 2 – 7
R9,591 ZAR for 5 nights
4.95 out of 5 average rating, 61 reviews