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Winston Salem Holiday Rentals

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58 rentals in Winston Salem.
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James Bond Hidden Cottage By Wake Forest University & Downtown

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Walking distance to Reynolda House and Gardens. Close to Wake Forest University

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
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Renovated Perfection in Winston-Salem Quiet Neighborhood

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
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Historical home with plenty of space in prime location

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
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An urban oasis in downtown Winston-Salem

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Adorable near Downtown and UNCSA

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
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Stylish, Comfortable, near UNCSA and Downtown

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 4
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Majestic Getaway Cabin near Wake Forest University

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
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Private & sweet patio level apartment in downtown Winston-Salem

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
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Outrageous House In The Woods

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
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Charming and Chic near UNCSA and Downtown Winston-Salem

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Historic 1940's home in Winston-Salem, sleeps 8, 4 queen bedrooms, 2 baths

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
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4BR Historic Home near downtown

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
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Beautifully renovated flat located in perfect downtown location.

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
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Privacy And Proximity

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 10
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Renowned historic home downtown/across from park

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 10
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✨Convenient to I-40, DT, Wake Forest, UNCSA, WSSU, Benton Center, & Hospitals✨

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
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Prestigious Buena Vista Near Downtown, Wake Forest University, Baptist Hospital

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Wake Forest area. Just right-2BR, wooded location, sleeps 5. Cute.

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
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Captains Quarters - Historical Home Downtown Rental

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
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Wake Forest College, Coliseum, Downtown Area

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
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Beautifully Furnished Downtown 1 BR, 1Ba Apartment 1870's Historic District

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
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Modern 1 Bedroom steps away from Wake Forest Hospital

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
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Beautiful apartment steps from Baptist Hospital in Central Winston-Salem

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
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One bedroom newly renovated steps from Wake Forest Hospital

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
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The Page's House A Perfect Place To Stay For Visiting Wake Forest University!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
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Gorgeous newly renovated apartment with King Bed, Parking, Laundry, and more!

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
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Historic Winston-Salem Guest Barn on Farm!

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
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Clean, Modern 1 bedroom Apartment

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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★The Treehouse Experience★Great location, Close to downtown, WFU, dining, fun

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Charming Cottage on Wooded Lot Close to Downtown

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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One Level Ranch home located on large farm property

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
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3 bedroom/3 bath.. Nice quite home all to yourself! Centrally Located

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
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Stylish 1BR Near Downtown & WFU Hospital

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Newly Renovated Apartment Only Steps from Wake Forest Hospital

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Newly Remodeled and Conveniently located steps from Wake Forest Hospital

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
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Convenient Apartment near Wake Forest Hospital and Downtown

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
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Sunlight facing entire Townhome 2 BR, 2.5 Bath

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
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Clean and quiet near Baptist hospital

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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2 Bedroom, 2 Bathroom in Downtown Winston-Salem

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Classic 1963 Serro Scotty Camper

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Sparkling clean KING BED, near WFU Hospital and Downtown

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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New, modern guest apartment in perfect location!

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Kasa | Self Check-In Studio+Steps Dining, Art District | Winston-Salem

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Kasa | Studio + Self Check-In, Craft Draft Crawl, Art District | Winston-Salem

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Kasa | Self Check-In, Pet Friendly + Steps to Dining | Winston-Salem

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Kasa | Perfect Family Spot + Fast WiFi, Self Check-In | Winston-Salem

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Kasa | Perfect for Families, Self Check-In - Art District | Winston-Salem

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Kasa | Near Historic WE Apt, Fast WiFi +Self Check-In | Winston-Salem

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Cozy, Convenient, Pet Friendly Ardmore House with Fenced in Yard!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
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Frequently Asked Questions about Winston Salem