Search results; Over 1,000 places in Winchester

Explore more homes

Top guest favorite
Room in Winchester
Stay with Holly
Winchester Private Room
Jul 25 – 30
R5,866 ZAR for 5 nights
4.98 out of 5 average rating, 118 reviews
Guest favorite
Townhouse in Winchester
Modern Elegance in Historic Old Town Winchester
2 beds
Aug 6 – 11
R14,185 ZAR for 5 nights
4.93 out of 5 average rating, 248 reviews
Top guest favorite
Home in Winchester
Cameron Charmer pristine w/double master suites
2 queen beds
Jul 14 – 19
R21,118 ZAR for 5 nights
4.97 out of 5 average rating, 197 reviews
Guest favorite
Home in Winchester
Indigo Blue modern open vibe on tree lined street
3 beds
Aug 3 – 8
R25,277 ZAR for 5 nights
4.95 out of 5 average rating, 191 reviews
Top guest favorite
Apartment in Winchester
Old Town Loft In Highly Desirable Area Downtown
1 queen bed
Jul 20 – 25
R13,839 ZAR for 5 nights
5.0 out of 5 average rating, 212 reviews
Guest favorite
Room in Winchester
Stay with PepperCustomer care,
Cheerful one bedroom available.
Aug 2 – 7
R5,397 ZAR for 5 nights
4.77 out of 5 average rating, 188 reviews
Guest favorite
Guest suite in Winchester
Retro Vibe Studio
1 queen bed
Aug 14 – 19
R10,261 ZAR for 5 nights
4.93 out of 5 average rating, 58 reviews
Guest favorite
Apartment in Winchester
Newly repurposed Historic Home in Winchester VA!
1 queen bed
Jul 24 – 29
R10,346 ZAR for 5 nights
4.92 out of 5 average rating, 108 reviews
Top guest favorite
Apartment in Winchester
Old Town Loft Modern Oasis In Downtown Winchester
2 beds
Jul 21 – 26
R17,364 ZAR for 5 nights
4.98 out of 5 average rating, 109 reviews
Top guest favorite
Home in Winchester
Cabin in Historic Old Town Winchester
2 king beds
Aug 18 – 23
R15,572 ZAR for 5 nights
4.95 out of 5 average rating, 42 reviews
Top guest favorite
Home in Winchester
Whole 3-bedroom house walkable to downtown.
4 beds
Aug 2 – 7
R17,278 ZAR for 5 nights
5.0 out of 5 average rating, 34 reviews
Guest favorite
Apartment in Winchester
Dreamweaver Bright 1BR 2 blocks to Walking Mall
1 bed
Aug 4 – 9
R15,998 ZAR for 5 nights
4.86 out of 5 average rating, 37 reviews
Top guest favorite
Condo in Winchester
Historic District Downtown Winchester
1 king bed
Jul 20 – 25
R22,078 ZAR for 5 nights
4.99 out of 5 average rating, 83 reviews
Superhost
Loft in Winchester
Immerse yourself in Old Town Winchester (Apt #4)
3 beds
Jul 31 – Aug 5
R8,597 ZAR for 5 nights
4.73 out of 5 average rating, 664 reviews
Guest favorite
Apartment in Winchester
Scarborough Fair walk to downtown two story apt
6 beds
Jul 15 – 20
R23,464 ZAR for 5 nights
4.91 out of 5 average rating, 112 reviews
Room in Stephens City
Stay with Racquel
Comfy 2BR | Work, Relax, Explore
Jul 14 – 19
R8,703 ZAR for 5 nights
New place to stay
Top guest favorite
Home in Winchester
Aunt Tim's Farmhouse
6 beds
Jul 15 – 20
R18,665 ZAR for 5 nights
4.96 out of 5 average rating, 132 reviews
Top guest favorite
Room in Stephens City
Stay with Clara
Room in Quiet Neighborhood
Aug 1 – 6
R5,141 ZAR for 5 nights
4.97 out of 5 average rating, 35 reviews