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Winston Salem Vacation Rentals

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

James Bond Hidden Cottage By Wake Forest University & Downtown

Rental Home
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Renovated Perfection in Winston-Salem Quiet Neighborhood, vacation rental in Winston Salem
Renovated Perfection in Winston-Salem Quiet Neighborhood, vacation rental in Winston Salem
Renovated Perfection in Winston-Salem Quiet Neighborhood, vacation rental in Winston Salem

Renovated Perfection in Winston-Salem Quiet Neighborhood

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Historical home with plenty of space in prime location, vacation rental in Winston Salem
Historical home with plenty of space in prime location, vacation rental in Winston Salem
Historical home with plenty of space in prime location, vacation rental in Winston Salem

Historical home with plenty of space in prime location

Rental Home
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Walking distance to Reynolda House and Gardens. Close to Wake Forest University

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Adorable near Downtown and UNCSA, vacation rental in Winston Salem
Adorable near Downtown and UNCSA, vacation rental in Winston Salem
Adorable near Downtown and UNCSA, vacation rental in Winston Salem

Adorable near Downtown and UNCSA

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Majestic Getaway Cabin near Wake Forest University, vacation rental in Winston Salem
Majestic Getaway Cabin near Wake Forest University, vacation rental in Winston Salem
Majestic Getaway Cabin near Wake Forest University, vacation rental in Winston Salem

Majestic Getaway Cabin near Wake Forest University

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Stylish, Comfortable, near UNCSA and Downtown, vacation rental in Winston Salem
Stylish, Comfortable, near UNCSA and Downtown, vacation rental in Winston Salem
Stylish, Comfortable, near UNCSA and Downtown, vacation rental in Winston Salem

Stylish, Comfortable, near UNCSA and Downtown

Rental Home
3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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An urban oasis in downtown Winston-Salem, vacation rental in Winston Salem
An urban oasis in downtown Winston-Salem, vacation rental in Winston Salem
An urban oasis in downtown Winston-Salem, vacation rental in Winston Salem

An urban oasis in downtown Winston-Salem

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Private & sweet patio level apartment in downtown Winston-Salem, vacation rental in Winston Salem
Private & sweet patio level apartment in downtown Winston-Salem, vacation rental in Winston Salem
Private & sweet patio level apartment in downtown Winston-Salem, vacation rental in Winston Salem

Private & sweet patio level apartment in downtown Winston-Salem

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Outrageous House In The Woods, vacation rental in Winston Salem
Outrageous House In The Woods, vacation rental in Winston Salem
Outrageous House In The Woods, vacation rental in Winston Salem

Outrageous House In The Woods

Rental Home
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Charming and Chic near UNCSA and Downtown Winston-Salem, vacation rental in Winston Salem
Charming and Chic near UNCSA and Downtown Winston-Salem, vacation rental in Winston Salem
Charming and Chic near UNCSA and Downtown Winston-Salem, vacation rental in Winston Salem

Charming and Chic near UNCSA and Downtown Winston-Salem

Rental Home
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

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Privacy And Proximity, vacation rental in Winston Salem
Privacy And Proximity, vacation rental in Winston Salem
Privacy And Proximity, vacation rental in Winston Salem

Privacy And Proximity

Rental Home
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Beautifully renovated flat located in perfect downtown location., vacation rental in Winston Salem
Beautifully renovated flat located in perfect downtown location., vacation rental in Winston Salem
Beautifully renovated flat located in perfect downtown location., vacation rental in Winston Salem

Beautifully renovated flat located in perfect downtown location.

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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4BR Historic Home near downtown, vacation rental in Winston Salem
4BR Historic Home near downtown, vacation rental in Winston Salem
4BR Historic Home near downtown, vacation rental in Winston Salem

4BR Historic Home near downtown

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Renowned historic home downtown/across from park, vacation rental in Winston Salem
Renowned historic home downtown/across from park, vacation rental in Winston Salem
Renowned historic home downtown/across from park, vacation rental in Winston Salem

Renowned historic home downtown/across from park

Rental Home
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Captains Quarters - Historical Home Downtown Rental, vacation rental in Winston Salem
Captains Quarters - Historical Home Downtown Rental, vacation rental in Winston Salem
Captains Quarters - Historical Home Downtown Rental, vacation rental in Winston Salem

Captains Quarters - Historical Home Downtown Rental

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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✨Convenient to I-40, DT, Wake Forest, UNCSA, WSSU, Benton Center, & Hospitals✨, vacation rental in Winston Salem
✨Convenient to I-40, DT, Wake Forest, UNCSA, WSSU, Benton Center, & Hospitals✨, vacation rental in Winston Salem
✨Convenient to I-40, DT, Wake Forest, UNCSA, WSSU, Benton Center, & Hospitals✨, vacation rental in Winston Salem

✨Convenient to I-40, DT, Wake Forest, UNCSA, WSSU, Benton Center, & Hospitals✨

Rental Home
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Prestigious Buena Vista Near Downtown, Wake Forest University, Baptist Hospital, vacation rental in Winston Salem
Prestigious Buena Vista Near Downtown, Wake Forest University, Baptist Hospital, vacation rental in Winston Salem
Prestigious Buena Vista Near Downtown, Wake Forest University, Baptist Hospital, vacation rental in Winston Salem

Prestigious Buena Vista Near Downtown, Wake Forest University, Baptist Hospital

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Modern 1 Bedroom steps away from Wake Forest Hospital, vacation rental in Winston Salem
Modern 1 Bedroom steps away from Wake Forest Hospital, vacation rental in Winston Salem
Modern 1 Bedroom steps away from Wake Forest Hospital, vacation rental in Winston Salem

Modern 1 Bedroom steps away from Wake Forest Hospital

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Wake Forest College, Coliseum, Downtown Area, vacation rental in Winston Salem
Wake Forest College, Coliseum, Downtown Area, vacation rental in Winston Salem
Wake Forest College, Coliseum, Downtown Area, vacation rental in Winston Salem

Wake Forest College, Coliseum, Downtown Area

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., vacation rental in Winston Salem
Wake Forest area. Just right-2BR, wooded location, sleeps 5. Cute., vacation rental in Winston Salem
Wake Forest area. Just right-2BR, wooded location, sleeps 5. Cute., vacation rental in Winston Salem

Wake Forest area. Just right-2BR, wooded location, sleeps 5. Cute.

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Beautifully Furnished Downtown 1 BR, 1Ba Apartment 1870's Historic District, vacation rental in Winston Salem
Beautifully Furnished Downtown 1 BR, 1Ba Apartment 1870's Historic District, vacation rental in Winston Salem
Beautifully Furnished Downtown 1 BR, 1Ba Apartment 1870's Historic District, vacation rental in Winston Salem

Beautifully Furnished Downtown 1 BR, 1Ba Apartment 1870's Historic District

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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One Level Ranch home located on large farm property, vacation rental in Winston Salem
One Level Ranch home located on large farm property, vacation rental in Winston Salem
One Level Ranch home located on large farm property, vacation rental in Winston Salem

One Level Ranch home located on large farm property

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Historic Winston-Salem Guest Barn on Farm!, vacation rental in Winston Salem
Historic Winston-Salem Guest Barn on Farm!, vacation rental in Winston Salem
Historic Winston-Salem Guest Barn on Farm!, vacation rental in Winston Salem

Historic Winston-Salem Guest Barn on Farm!

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Beautiful apartment steps from Baptist Hospital in Central Winston-Salem

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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The Page's House A Perfect Place To Stay For Visiting Wake Forest University!, vacation rental in Winston Salem
The Page's House A Perfect Place To Stay For Visiting Wake Forest University!, vacation rental in Winston Salem
The Page's House A Perfect Place To Stay For Visiting Wake Forest University!, vacation rental in Winston Salem

The Page's House A Perfect Place To Stay For Visiting Wake Forest University!

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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One bedroom newly renovated steps from Wake Forest Hospital, vacation rental in Winston Salem
One bedroom newly renovated steps from Wake Forest Hospital, vacation rental in Winston Salem
One bedroom newly renovated steps from Wake Forest Hospital, vacation rental in Winston Salem

One bedroom newly renovated steps from Wake Forest Hospital

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Gorgeous newly renovated apartment with King Bed, Parking, Laundry, and more!, vacation rental in Winston Salem
Gorgeous newly renovated apartment with King Bed, Parking, Laundry, and more!, vacation rental in Winston Salem
Gorgeous newly renovated apartment with King Bed, Parking, Laundry, and more!, vacation rental in Winston Salem

Gorgeous newly renovated apartment with King Bed, Parking, Laundry, and more!

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Clean, Modern 1 bedroom Apartment, vacation rental in Winston Salem
Clean, Modern 1 bedroom Apartment, vacation rental in Winston Salem
Clean, Modern 1 bedroom Apartment, vacation rental in Winston Salem

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, vacation rental in Winston Salem
★The Treehouse Experience★Great location, Close to downtown, WFU, dining, fun, vacation rental in Winston Salem
★The Treehouse Experience★Great location, Close to downtown, WFU, dining, fun, vacation rental in Winston Salem

★The Treehouse Experience★Great location, Close to downtown, WFU, dining, fun

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Charming Cottage on Wooded Lot Close to Downtown, vacation rental in Winston Salem
Charming Cottage on Wooded Lot Close to Downtown, vacation rental in Winston Salem
Charming Cottage on Wooded Lot Close to Downtown, vacation rental in Winston Salem

Charming Cottage on Wooded Lot Close to Downtown

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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3 bedroom/3 bath.. Nice quite home all to yourself! Centrally Located, vacation rental in Winston Salem
3 bedroom/3 bath.. Nice quite home all to yourself! Centrally Located, vacation rental in Winston Salem
3 bedroom/3 bath.. Nice quite home all to yourself! Centrally Located, vacation rental in Winston Salem

3 bedroom/3 bath.. Nice quite home all to yourself! Centrally Located

Rental Home
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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Stylish 1BR Near Downtown & WFU Hospital, vacation rental in Winston Salem
Stylish 1BR Near Downtown & WFU Hospital, vacation rental in Winston Salem
Stylish 1BR Near Downtown & WFU Hospital, vacation rental in Winston Salem

Stylish 1BR Near Downtown & WFU Hospital

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Newly Renovated Apartment Only Steps from Wake Forest Hospital, vacation rental in Winston Salem
Newly Renovated Apartment Only Steps from Wake Forest Hospital, vacation rental in Winston Salem
Newly Renovated Apartment Only Steps from Wake Forest Hospital, vacation rental in Winston Salem

Newly Renovated Apartment Only Steps from Wake Forest Hospital

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Newly Remodeled and Conveniently located steps from Wake Forest Hospital, vacation rental in Winston Salem
Newly Remodeled and Conveniently located steps from Wake Forest Hospital, vacation rental in Winston Salem
Newly Remodeled and Conveniently located steps from Wake Forest Hospital, vacation rental in Winston Salem

Newly Remodeled and Conveniently located steps from Wake Forest Hospital

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Convenient Apartment near Wake Forest Hospital and Downtown, vacation rental in Winston Salem
Convenient Apartment near Wake Forest Hospital and Downtown, vacation rental in Winston Salem
Convenient Apartment near Wake Forest Hospital and Downtown, vacation rental in Winston Salem

Convenient Apartment near Wake Forest Hospital and Downtown

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Clean and quiet near Baptist hospital, vacation rental in Winston Salem
Clean and quiet near Baptist hospital, vacation rental in Winston Salem
Clean and quiet near Baptist hospital, vacation rental in Winston Salem

Clean and quiet near Baptist hospital

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Sunlight facing entire Townhome 2 BR, 2.5 Bath, vacation rental in Winston Salem
Sunlight facing entire Townhome 2 BR, 2.5 Bath, vacation rental in Winston Salem
Sunlight facing entire Townhome 2 BR, 2.5 Bath, vacation rental in Winston Salem

Sunlight facing entire Townhome 2 BR, 2.5 Bath

Rental Home
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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Classic 1963 Serro Scotty Camper, vacation rental in Winston Salem
Classic 1963 Serro Scotty Camper, vacation rental in Winston Salem
Classic 1963 Serro Scotty Camper, vacation rental in Winston Salem

Classic 1963 Serro Scotty Camper

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Sparkling clean KING BED, near WFU Hospital and Downtown, vacation rental in Winston Salem
Sparkling clean KING BED, near WFU Hospital and Downtown, vacation rental in Winston Salem
Sparkling clean KING BED, near WFU Hospital and Downtown, vacation rental in Winston Salem

Sparkling clean KING BED, near WFU Hospital and Downtown

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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New, modern guest apartment in perfect location!, vacation rental in Winston Salem
New, modern guest apartment in perfect location!, vacation rental in Winston Salem
New, modern guest apartment in perfect location!, vacation rental in Winston Salem

New, modern guest apartment in perfect location!

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

2 Bedroom, 2 Bathroom in Downtown Winston-Salem

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
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Kasa | Perfect Family Spot + Fast WiFi, Self Check-In | Winston-Salem, vacation rental in Winston Salem
Kasa | Perfect Family Spot + Fast WiFi, Self Check-In | Winston-Salem, vacation rental in Winston Salem
Kasa | Perfect Family Spot + Fast WiFi, Self Check-In | Winston-Salem, vacation rental in Winston Salem

Kasa | Perfect Family Spot + Fast WiFi, Self Check-In | Winston-Salem

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Kasa | Studio + Self Check-In, Craft Draft Crawl, Art District | Winston-Salem, vacation rental in Winston Salem
Kasa | Studio + Self Check-In, Craft Draft Crawl, Art District | Winston-Salem, vacation rental in Winston Salem
Kasa | Studio + Self Check-In, Craft Draft Crawl, Art District | Winston-Salem, vacation rental in Winston Salem

Kasa | Studio + Self Check-In, Craft Draft Crawl, Art District | Winston-Salem

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Kasa | Self Check-In Studio+Steps Dining, Art District | Winston-Salem, vacation rental in Winston Salem
Kasa | Self Check-In Studio+Steps Dining, Art District | Winston-Salem, vacation rental in Winston Salem
Kasa | Self Check-In Studio+Steps Dining, Art District | Winston-Salem, vacation rental in Winston Salem

Kasa | Self Check-In Studio+Steps Dining, Art District | Winston-Salem

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

Kasa | Self Check-In, Pet Friendly + Steps to Dining | Winston-Salem

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Kasa | Near Historic WE Apt, Fast WiFi +Self Check-In | Winston-Salem, vacation rental in Winston Salem
Kasa | Near Historic WE Apt, Fast WiFi +Self Check-In | Winston-Salem, vacation rental in Winston Salem
Kasa | Near Historic WE Apt, Fast WiFi +Self Check-In | Winston-Salem, vacation rental in Winston Salem

Kasa | Near Historic WE Apt, Fast WiFi +Self Check-In | Winston-Salem

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Kasa | WFH + Fast WiFi, Contactless Check-In, Art District | Winston-Salem, vacation rental in Winston Salem
Kasa | WFH + Fast WiFi, Contactless Check-In, Art District | Winston-Salem, vacation rental in Winston Salem
Kasa | WFH + Fast WiFi, Contactless Check-In, Art District | Winston-Salem, vacation rental in Winston Salem

Kasa | WFH + Fast WiFi, Contactless Check-In, Art District | Winston-Salem

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
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Kasa | Perfect for Families, Self Check-In - Art District | Winston-Salem, vacation rental in Winston Salem
Kasa | Perfect for Families, Self Check-In - Art District | Winston-Salem, vacation rental in Winston Salem
Kasa | Perfect for Families, Self Check-In - Art District | Winston-Salem, vacation rental in Winston Salem

Kasa | Perfect for Families, Self Check-In - Art District | Winston-Salem

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Frequently Asked Questions about Winston Salem