Search results; Over 1,000 places in Winchester

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Guest favorite
Home in Winchester
Colonial Getaway Near Old Town Historic Winchester
6 guests3 bedrooms4 beds2.5 baths
Jul 27 – Aug 1
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Jul 27 – Aug 1
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R16,469 ZAR for 5 nights

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Top guest favorite
Room in Winchester
Stay with Holly
Winchester Private Room
Jul 25 – 30
R5,814 ZAR for 5 nights
4.98 out of 5 average rating, 118 reviews
Guest favorite
Room in Winchester
Stay with PepperCustomer care,
Cheerful one bedroom available.
Aug 2 – 7
R5,518 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
3 beds
Aug 3 – 8
R25,052 ZAR for 5 nights
4.95 out of 5 average rating, 191 reviews
Guest favorite
Townhouse in Winchester
Modern Elegance in Historic Old Town Winchester
2 beds
Aug 3 – 8
R13,214 ZAR for 5 nights
4.93 out of 5 average rating, 246 reviews
Top guest favorite
Home in Winchester
Cabin in Historic Old Town Winchester
2 king beds
Jul 29 – Aug 3
R15,433 ZAR for 5 nights
4.95 out of 5 average rating, 42 reviews
Guest favorite
Guest suite in Winchester
Retro Vibe Studio
1 queen bed
Aug 14 – 19
R10,148 ZAR for 5 nights
4.93 out of 5 average rating, 58 reviews
Top guest favorite
Home in Winchester
Cameron Charmer pristine w/double master suites
2 queen beds
Jul 14 – 19
R20,930 ZAR for 5 nights
4.97 out of 5 average rating, 197 reviews
Superhost
Loft in Winchester
Immerse yourself in Old Town Winchester (Apt #4)
3 beds
Jul 31 – Aug 5
R8,499 ZAR for 5 nights
4.73 out of 5 average rating, 662 reviews
Guest favorite
Guest suite in Winchester
Safe, cozy oasis with private living & bath.
2 beds
Aug 1 – 6
R9,907 ZAR for 5 nights
4.81 out of 5 average rating, 342 reviews
Guest favorite
Apartment in Winchester
Newly repurposed Historic Home in Winchester VA!
1 queen bed
Jul 17 – 22
R10,317 ZAR for 5 nights
4.92 out of 5 average rating, 108 reviews
Top guest favorite
Room in Stephens City
Stay with Clara
Room in Quiet Neighborhood
Jul 18 – 23
R5,095 ZAR for 5 nights
4.97 out of 5 average rating, 35 reviews
Top guest favorite
Home in Winchester
Whole 3-bedroom house walkable to downtown.
4 beds
Aug 2 – 7
R17,125 ZAR for 5 nights
5.0 out of 5 average rating, 34 reviews
Top guest favorite
Home in Inwood
The Inwood House- easy on/off I-81
2 beds
Jul 20 – 25
R11,564 ZAR for 5 nights
4.96 out of 5 average rating, 470 reviews
Top guest favorite
Apartment in Winchester
Old Town Loft In Highly Desirable Area Downtown
1 queen bed
Jul 20 – 25
R14,144 ZAR for 5 nights
5.0 out of 5 average rating, 211 reviews
Guest favorite
Cabin in Front Royal
The Wizard's Chalet • Cozy nature escape • Hot Tub
3 beds
Sep 20 – 25
R25,594 ZAR for 5 nights
4.94 out of 5 average rating, 217 reviews
Guest favorite
Apartment in Winchester
Scarborough Fair walk to downtown two story apt
6 beds
Jul 15 – 20
R23,255 ZAR for 5 nights
4.91 out of 5 average rating, 112 reviews
Guest favorite
Apartment in Winchester
Historic Wisteria House on Old Town Walking Mall
1 queen bed
Sep 2 – 7
R16,533 ZAR for 5 nights
4.96 out of 5 average rating, 103 reviews
Top guest favorite
Apartment in Winchester
Old Town Loft Modern Oasis In Downtown Winchester
2 beds
Jul 21 – 26
R18,351 ZAR for 5 nights
4.98 out of 5 average rating, 109 reviews