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
R5,823 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
R5,526 ZAR for 5 nights
4.77 out of 5 average rating, 188 reviews
Guest favorite
Townhouse in Winchester
Modern Elegance in Historic Old Town Winchester
2 beds
Aug 6 – 11
R14,122 ZAR for 5 nights
4.93 out of 5 average rating, 247 reviews
Guest favorite
Home in Winchester
Indigo Blue modern open vibe on tree lined street
3 beds
Aug 3 – 8
R25,088 ZAR for 5 nights
4.95 out of 5 average rating, 191 reviews
Guest favorite
Guest suite in Winchester
Safe, cozy oasis with private living & bath.
2 beds
Aug 1 – 6
R9,921 ZAR for 5 nights
4.81 out of 5 average rating, 342 reviews
Top guest favorite
Home in Winchester
Cameron Charmer pristine w/double master suites
2 queen beds
Jul 14 – 19
R20,960 ZAR for 5 nights
4.97 out of 5 average rating, 197 reviews
Guest favorite
Apartment in Winchester
Newly repurposed Historic Home in Winchester VA!
1 queen bed
Jul 17 – 22
R10,332 ZAR for 5 nights
4.92 out of 5 average rating, 108 reviews
Top guest favorite
Room in Winchester
Stay with GaryJoy! fun! respect!,
We Welcome You to Winchester! Best reviews!
Jul 10 – 15
R9,231 ZAR for 5 nights
4.92 out of 5 average rating, 217 reviews
Cabin in Slanesville
Stunning Mountain Views w/Deck & Grill on 5 Acres!
2 single beds
Jul 12 – 17
R9,308 ZAR for 5 nights
New place to stay
Superhost
Loft in Winchester
Immerse yourself in Old Town Winchester (Apt #4)
3 beds
Jul 31 – Aug 5
R8,511 ZAR for 5 nights
4.73 out of 5 average rating, 663 reviews
Top guest favorite
Room in Stephens City
Stay with Clara
Room in Quiet Neighborhood
Jul 19 – 24
R5,039 ZAR for 5 nights
4.97 out of 5 average rating, 35 reviews
Top guest favorite
Home in Winchester
Cabin in Historic Old Town Winchester
2 king beds
Jul 29 – Aug 3
R15,455 ZAR for 5 nights
4.95 out of 5 average rating, 42 reviews
Top guest favorite
Room in Bunker Hill
Stay with KevinApplication engineer,
Hollystay Room 1
Jul 25 – 30
R5,928 ZAR for 5 nights
5.0 out of 5 average rating, 39 reviews
Top guest favorite
Home in Winchester
Colonial Getaway Near Old Town Historic Winchester
4 beds
Jul 27 – Aug 1
R16,493 ZAR for 5 nights
4.97 out of 5 average rating, 204 reviews
Top guest favorite
Home in Inwood
The Inwood House- easy on/off I-81
2 beds
Jul 20 – 25
R11,581 ZAR for 5 nights
4.96 out of 5 average rating, 470 reviews
Guest favorite
Apartment in Winchester
Dreamweaver Bright 1BR 2 blocks to Walking Mall
1 bed
Aug 4 – 9
R15,879 ZAR for 5 nights
4.86 out of 5 average rating, 37 reviews
Room in Stephens City
Stay with Racquel
Comfy 2BR | Work, Relax, Explore
Jul 10 – 15
R8,638 ZAR for 5 nights
New place to stay
Chalet in Bluemont
Emberwood | Modern Chalet + Spa + Stargazing Dome
3 beds
Jul 13 – 18
R25,342 ZAR for 5 nights
New place to stay