Search results; Over 1,000 places in Winchester

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Guest favorite
Condo in Winchester
Historic District Downtown Winchester
2 guests1 bedroom1 bed1 bath
Jul 20 – 25
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Jul 20 – 25
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R21,609 ZAR for 5 nights

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Top guest favorite
Apartment in Winchester
Old Town Loft In Highly Desirable Area Downtown
Free cancellation
Jul 13 – 18
R13,545 ZAR for 5 nights
5.0 out of 5 average rating, 210 reviews
Top guest favorite
Room in Winchester
Stay with Holly
Winchester Private Room
Jul 25 – 30
R5,742 ZAR for 5 nights
4.98 out of 5 average rating, 115 reviews
Guest favorite
Townhouse in Winchester
Modern Elegance in Historic Old Town Winchester
Free cancellation
Jul 19 – 24
R13,467 ZAR for 5 nights
4.93 out of 5 average rating, 246 reviews
Guest favorite
Room in Winchester
Stay with PepperCustomer care,
Cheerful one bedroom available.
Jul 9 – 14
R3,592 ZAR for 5 nights
4.77 out of 5 average rating, 188 reviews
Guest favorite
Home in Winchester
Indigo Blue modern open vibe on tree lined street
Free cancellation
Aug 3 – 8
R24,741 ZAR for 5 nights
4.95 out of 5 average rating, 191 reviews
Guest favorite
Guest suite in Winchester
Retro Vibe Studio
Free cancellation
Aug 14 – 19
R10,022 ZAR for 5 nights
4.93 out of 5 average rating, 58 reviews
Top guest favorite
Home in Winchester
Cabin in Historic Old Town Winchester
2 king beds
Jul 7 – 12
R15,242 ZAR for 5 nights
4.95 out of 5 average rating, 42 reviews
Top guest favorite
Room in Stephens City
Stay with Clara
Room in Quiet Neighborhood
Jul 6 – 11
R4,907 ZAR for 5 nights
4.97 out of 5 average rating, 35 reviews
Guest favorite
Apartment in Winchester
Scarborough Fair walk to downtown two story apt
6 beds
Jul 5 – 10
R23,154 ZAR for 5 nights
4.91 out of 5 average rating, 111 reviews
Guest favorite
Guest suite in Winchester
Safe, cozy oasis with private living & bath.
2 beds
Jul 6 – 11
R9,709 ZAR for 5 nights
4.81 out of 5 average rating, 341 reviews
Top guest favorite
Room in Winchester
Stay with GaryJoy! fun! respect!,
We Welcome You to Winchester! Best reviews!
Jul 3 – 8
R9,103 ZAR for 5 nights
4.92 out of 5 average rating, 217 reviews
Top guest favorite
Room in Stephens City
Stay with Racquel
Comfy 1BR | Work, Relax, Explore
Jul 10 – 15
R6,400 ZAR for 5 nights
5.0 out of 5 average rating, 5 reviews
Superhost
Apartment in Winchester
Downtown 1920's Gas Station with Hot Tub
Free cancellation
Aug 10 – 15
R15,137 ZAR for 5 nights
4.9 out of 5 average rating, 356 reviews
Top guest favorite
Home in Winchester
Cameron Charmer pristine w/double master suites
Free cancellation
Jul 14 – 19
R20,670 ZAR for 5 nights
4.97 out of 5 average rating, 196 reviews
Top guest favorite
Home in Winchester
Colonial Getaway Near Old Town Historic Winchester
Free cancellation
Jul 27 – Aug 1
R16,265 ZAR for 5 nights
4.97 out of 5 average rating, 202 reviews
Guest favorite
Apartment in Winchester
Downtowner
Free cancellation
Jul 13 – 18
R13,049 ZAR for 5 nights
4.97 out of 5 average rating, 284 reviews
Top guest favorite
Home in Inwood
The Inwood House- easy on/off I-81
Free cancellation
Jul 6 – 11
R11,379 ZAR for 5 nights
4.96 out of 5 average rating, 467 reviews
Top guest favorite
Home in Winchester
City Charmer minutes from Old Town
Free cancellation
Jul 27 – Aug 1
R11,191 ZAR for 5 nights
4.97 out of 5 average rating, 255 reviews