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Guest favorite
Apartment in Winchester
Cameron Grace brand new downtown 1 BR loft
2 guests1 bedroom1 bed1 bath
Jun 1 – 6
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Jun 1 – 6
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R3,281 ZAR per night

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Top guest favorite
Room in Winchester
Stay with Holly
Winchester Private Room
Apr 2 – 7
R1,203 ZAR per night
4.98 out of 5 average rating, 90 reviews
Guest favorite
Townhouse in Winchester
Modern Elegance in Historic Old Town Winchester
Free cancellation
Apr 7 – 12
R2,486 ZAR per night
4.93 out of 5 average rating, 229 reviews
Guest favorite
Home in Winchester
Historic District Charm On Cameron Street
3 beds
Mar 13 – 18
R3,306 ZAR per night
4.94 out of 5 average rating, 150 reviews
Top guest favorite
Home in Winchester
City Charmer minutes from Old Town
2 beds
Mar 15 – 20
R2,208 ZAR per night
4.97 out of 5 average rating, 241 reviews
Top guest favorite
Home in Winchester
Downtown Chic Condo w/parking
Mar 14 – 19
R2,596 ZAR per night
5.0 out of 5 average rating, 45 reviews
Room in Winchester
Stay with LeroyMath teacher,
Family Friendly Retreat #5
Mar 21 – 26
R422 ZAR per night
New place to stay
Superhost
Loft in Winchester
Immerse yourself in Old Town Winchester (Apt #4)
Free cancellation
Apr 4 – 9
R1,591 ZAR per night
4.72 out of 5 average rating, 639 reviews
Top guest favorite
Apartment in Winchester
Downtowner
3 beds
Mar 16 – 21
R2,634 ZAR per night
4.97 out of 5 average rating, 267 reviews
Guest favorite
Apartment in Winchester
Easy like a Sunday Morning 1 BR apt great location
1 bed
Mar 16 – 21
R1,520 ZAR per night
4.97 out of 5 average rating, 59 reviews
Guest favorite
Apartment in Winchester
Newly repurposed Historic Home in Winchester VA!
Free cancellation
Mar 16 – 21
R1,809 ZAR per night
4.91 out of 5 average rating, 95 reviews
Guest favorite
Home in Winchester
Juliana Spa Suite - Entire Main Floor
1 king bed
Mar 13 – 18
R1,783 ZAR per night
5.0 out of 5 average rating, 8 reviews
Guest favorite
Home in Winchester
Indigo Blue modern open vibe on tree lined street
Free cancellation
Mar 30 – Apr 4
R5,075 ZAR per night
4.94 out of 5 average rating, 179 reviews
Guest favorite
Room in Winchester
Stay with PepperCustomer care,
Cheerful one bedroom available.
Mar 23 – 28
R702 ZAR per night
4.77 out of 5 average rating, 163 reviews
Top guest favorite
Apartment in Winchester
Old Town Loft In Highly Desirable Area Downtown
Free cancellation
Mar 30 – Apr 4
R2,996 ZAR per night
5.0 out of 5 average rating, 193 reviews
Guest favorite
Apartment in Winchester
Downtown 1920's Gas Station with Hot Tub
1 queen bed
Mar 19 – 24
R3,502 ZAR per night
4.91 out of 5 average rating, 327 reviews
Top guest favorite
Condo in Winchester
Historic District Downtown Winchester
1 king bed
Mar 13 – 18
R3,075 ZAR per night
4.99 out of 5 average rating, 72 reviews
Top guest favorite
Apartment in Winchester
Old Town Loft Modern Oasis In Downtown Winchester
Free cancellation
Mar 30 – Apr 4
R3,558 ZAR per night
4.98 out of 5 average rating, 97 reviews
Top guest favorite
Apartment in Winchester
Modern Twist in Old Town! Rock n' Roll FUN!
2 beds
Mar 13 – 18
R2,443 ZAR per night
4.93 out of 5 average rating, 148 reviews