Search results; Over 1,000 homes in Winchester

Top guest favorite
Home in Winchester
City Charmer minutes from Old Town
Free cancellation
Aug 16 – 21
R12,150 ZAR for 5 nights
4.97 out of 5 average rating, 256 reviews
Guest favorite
Apartment in Winchester
Newly repurposed Historic Home in Winchester VA!
Free cancellation
Jul 24 – 29
R10,305 ZAR for 5 nights
4.92 out of 5 average rating, 108 reviews
Top guest favorite
Home in Winchester
Aunt Tim's Farmhouse
6 beds
Jul 17 – 22
R18,553 ZAR for 5 nights
4.96 out of 5 average rating, 132 reviews
Guest favorite
Guest suite in Winchester
Safe, cozy oasis with private living & bath.
2 beds
Aug 1 – 6
R9,898 ZAR for 5 nights
4.81 out of 5 average rating, 344 reviews
Top guest favorite
Home in Winchester
Colonial Getaway Near Old Town Historic Winchester
Free cancellation
Aug 1 – 6
R17,387 ZAR for 5 nights
4.97 out of 5 average rating, 204 reviews
Guest favorite
Cabin in Winchester
Foxtrot Mokki | Secluded Getaway 2 Hours from DC
Free cancellation
Aug 24 – 29
R19,889 ZAR for 5 nights
4.94 out of 5 average rating, 90 reviews
Guest favorite
Home in Inwood
Arden House, Inwood WV
Free cancellation
Aug 4 – 9
R7,952 ZAR for 5 nights
4.87 out of 5 average rating, 660 reviews
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More stays available for your dates

Top guest favorite
Cabin in Gerrardstown
The Nest: Cozy Chalet w/Wi-Fi, Deck & Grill
Free cancellation
Aug 17 – 22
R16,653 ZAR for 5 nights, originally R19,054 ZAR
4.98 out of 5 average rating, 158 reviews
Apartment in Winchester
The Queen of Winchester - Three Bedroom Apartment
Jul 18 – 23
R10,199 ZAR for 5 nights
4.81 out of 5 average rating, 26 reviews
Top guest favorite
Boutique hotel in Capon Bridge
Paw Paw Suite ~ 1 of 5 Unique Stays at Basswood
1 queen bed
Aug 10 – 15
R7,736 ZAR for 5 nights
4.99 out of 5 average rating, 197 reviews
Superhost
Home in Winchester
Dog Friendly Mountain Retreat w/ Hot Tub & Firepit
Free cancellation
Jul 24 – 29
R17,928 ZAR for 5 nights, originally R21,575 ZAR
4.78 out of 5 average rating, 18 reviews
Top guest favorite
Apartment in Charles Town
Private efficiency apartment
1 double bed
Jul 20 – 25
R9,542 ZAR for 5 nights
4.97 out of 5 average rating, 598 reviews
Top guest favorite
Cottage in Martinsburg
Last Rodeo Cottage
Free cancellation
Aug 13 – 18
R12,489 ZAR for 5 nights
4.98 out of 5 average rating, 425 reviews
Guest favorite
Cabin in Front Royal
The Wizard's Chalet • Cozy nature escape • Hot Tub
Free cancellation
Sep 28 – Oct 3
R22,711 ZAR for 5 nights, originally R24,635 ZAR
4.95 out of 5 average rating, 219 reviews
Guest favorite
Cabin in Winchester
Spectacular Views w/ Hot tub, Fire Pit, King Beds
3 beds
Aug 1 – 6
R28,472 ZAR for 5 nights
4.96 out of 5 average rating, 101 reviews
Barn in Berryville
Modern House Barn on 66 acre Horse Farm
3 beds
Jul 26 – 31
R14,418 ZAR for 5 nights, originally R16,024 ZAR
4.76 out of 5 average rating, 123 reviews
Top guest favorite
Boutique hotel in Capon Bridge
Sycamore Suite ~ 1 of 5 Unique Stays at Basswood
2 beds
Jul 23 – 28
R9,727 ZAR for 5 nights
4.98 out of 5 average rating, 154 reviews
Top guest favorite
Campsite in Front Royal
Blue Mountain Hideaway • Enchanting Glamping Stay
Free cancellation
Aug 3 – 8
R13,464 ZAR for 5 nights, originally R15,400 ZAR
4.99 out of 5 average rating, 200 reviews