We noticed that you're using an unsupported browser. The Tripadvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Winston Salem Holiday Apartments

List your property
Owner log in
Where to?
Check-in
— / — / —
Check-out
— / — / —
Guests
0 rooms, 2+ guests

Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Distance from

1 km
140 rentals in Winston Salem.
Sort by:
Tripadvisor Sort
Revenue impacts this sort order. Learn more.
The James Bond Hidden Cottage By Wake Forest University & Downtown, holiday rental in Winston Salem
The James Bond Hidden Cottage By Wake Forest University & Downtown, holiday rental in Winston Salem
The James Bond Hidden Cottage By Wake Forest University & Downtown, holiday rental in Winston Salem

The James Bond Hidden Cottage By Wake Forest University & Downtown

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out

Historic Beauty: 5BR Home with Yard Near Hospital, holiday rental in Winston Salem
Historic Beauty: 5BR Home with Yard Near Hospital, holiday rental in Winston Salem
Historic Beauty: 5BR Home with Yard Near Hospital, holiday rental in Winston Salem

Historic Beauty: 5BR Home with Yard Near Hospital

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out

Majestic Getaway Cabin near Wake Forest University, holiday rental in Winston Salem
Majestic Getaway Cabin near Wake Forest University, holiday rental in Winston Salem
Majestic Getaway Cabin near Wake Forest University, holiday rental in Winston Salem

Majestic Getaway Cabin near Wake Forest University

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out

Renovated Perfection in Winston-Salem Quiet Neighborhood, holiday rental in Winston Salem
Renovated Perfection in Winston-Salem Quiet Neighborhood, holiday rental in Winston Salem
Renovated Perfection in Winston-Salem Quiet Neighborhood, holiday rental in Winston Salem

Renovated Perfection in Winston-Salem Quiet Neighborhood

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out

Adorable near UNCSA and Downtown, holiday rental in Winston Salem
Adorable near UNCSA and Downtown, holiday rental in Winston Salem
Adorable near UNCSA and Downtown, holiday rental in Winston Salem

Adorable near UNCSA and Downtown

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out

An urban oasis in downtown Winston-Salem, holiday rental in Winston Salem
An urban oasis in downtown Winston-Salem, holiday rental in Winston Salem
An urban oasis in downtown Winston-Salem, holiday rental in Winston Salem

An urban oasis in downtown Winston-Salem

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out

Walking distance to Reynolda House and Gardens. Close to Wake Forest University

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out

Charming and Chic near UNCSA and Downtown Winston-Salem, holiday rental in Winston Salem
Charming and Chic near UNCSA and Downtown Winston-Salem, holiday rental in Winston Salem
Charming and Chic near UNCSA and Downtown Winston-Salem, holiday rental in Winston Salem

Charming and Chic near UNCSA and Downtown Winston-Salem

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out

Modern, Stylish near UNCSA and Downtown, holiday rental in Winston Salem
Modern, Stylish near UNCSA and Downtown, holiday rental in Winston Salem
Modern, Stylish near UNCSA and Downtown, holiday rental in Winston Salem

Modern, Stylish near UNCSA and Downtown

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out

Private & sweet patio level apartment in downtown Winston-Salem, holiday rental in Winston Salem
Private & sweet patio level apartment in downtown Winston-Salem, holiday rental in Winston Salem
Private & sweet patio level apartment in downtown Winston-Salem, holiday rental in Winston Salem

Private & sweet patio level apartment in downtown Winston-Salem

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out

Save time - get the best Winston Salem rentals sent straight to your email!
Outrageous House In The Woods, holiday rental in Winston Salem
Outrageous House In The Woods, holiday rental in Winston Salem
Outrageous House In The Woods, holiday rental in Winston Salem

Outrageous House In The Woods

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out

Privacy And Proximity, holiday rental in Winston Salem
Privacy And Proximity, holiday rental in Winston Salem
Privacy And Proximity, holiday rental in Winston Salem

Privacy And Proximity

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out

Beautifully renovated flat located in perfect downtown location., holiday rental in Winston Salem
Beautifully renovated flat located in perfect downtown location., holiday rental in Winston Salem
Beautifully renovated flat located in perfect downtown location., holiday rental in Winston Salem

Beautifully renovated flat located in perfect downtown location.

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out

Historic 1940's home in Winston-Salem, sleeps 8, 4 queen bedrooms, 2 baths

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out

Luxurious, Historic 4BR Home in Downtown Winston, holiday rental in Winston Salem
Luxurious, Historic 4BR Home in Downtown Winston, holiday rental in Winston Salem
Luxurious, Historic 4BR Home in Downtown Winston, holiday rental in Winston Salem

Luxurious, Historic 4BR Home in Downtown Winston

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out

Renowned historic home downtown/across from park, holiday rental in Winston Salem
Renowned historic home downtown/across from park, holiday rental in Winston Salem
Renowned historic home downtown/across from park, holiday rental in Winston Salem

Renowned historic home downtown/across from park

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out

Captains Quarters - Historical Home Downtown Rental, holiday rental in Winston Salem
Captains Quarters - Historical Home Downtown Rental, holiday rental in Winston Salem
Captains Quarters - Historical Home Downtown Rental, holiday rental in Winston Salem

Captains Quarters - Historical Home Downtown Rental

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out

Wake Forest College, Coliseum, Downtown Area, holiday rental in Winston Salem
Wake Forest College, Coliseum, Downtown Area, holiday rental in Winston Salem
Wake Forest College, Coliseum, Downtown Area, holiday rental in Winston Salem

Wake Forest College, Coliseum, Downtown Area

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out

Prestigious Buena Vista Near Downtown, Wake Forest University, Baptist Hospital, holiday rental in Winston Salem
Prestigious Buena Vista Near Downtown, Wake Forest University, Baptist Hospital, holiday rental in Winston Salem
Prestigious Buena Vista Near Downtown, Wake Forest University, Baptist Hospital, holiday rental in Winston Salem

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

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out

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

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

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out

Newly Renovated Hidden Gem Close to Winston/Kernersville, holiday rental in Winston Salem
Newly Renovated Hidden Gem Close to Winston/Kernersville, holiday rental in Winston Salem
Newly Renovated Hidden Gem Close to Winston/Kernersville, holiday rental in Winston Salem

Newly Renovated Hidden Gem Close to Winston/Kernersville

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out

✨Convenient to I-40, DT, Wake Forest, UNCSA, WSSU, Benton Center, & Hospitals✨, holiday rental in Winston Salem
✨Convenient to I-40, DT, Wake Forest, UNCSA, WSSU, Benton Center, & Hospitals✨, holiday rental in Winston Salem
✨Convenient to I-40, DT, Wake Forest, UNCSA, WSSU, Benton Center, & Hospitals✨, holiday rental in Winston Salem

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

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out

Beautifully furnished downtown 1 BR, 1Ba Apartment 1870s historic district, holiday rental in Winston Salem
Beautifully furnished downtown 1 BR, 1Ba Apartment 1870s historic district, holiday rental in Winston Salem
Beautifully furnished downtown 1 BR, 1Ba Apartment 1870s historic district, holiday rental in Winston Salem

Beautifully furnished downtown 1 BR, 1Ba Apartment 1870s historic district

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out

Trendy 1 BR w/KING Bed in Central Location, holiday rental in Winston Salem
Trendy 1 BR w/KING Bed in Central Location, holiday rental in Winston Salem
Trendy 1 BR w/KING Bed in Central Location, holiday rental in Winston Salem

Trendy 1 BR w/KING Bed in Central Location

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out

Ranch farmhouse on 14 acres. Quiet and Relaxing., holiday rental in Winston Salem
Ranch farmhouse on 14 acres. Quiet and Relaxing., holiday rental in Winston Salem
Ranch farmhouse on 14 acres. Quiet and Relaxing., holiday rental in Winston Salem

Ranch farmhouse on 14 acres. Quiet and Relaxing.

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out

Historic Winston-Salem Guest Barn on Farm!, holiday rental in Winston Salem
Historic Winston-Salem Guest Barn on Farm!, holiday rental in Winston Salem
Historic Winston-Salem Guest Barn on Farm!, holiday rental in Winston Salem

Historic Winston-Salem Guest Barn on Farm!

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out

Nice quite home all to yourself! Centrally Located, holiday rental in Winston Salem
Nice quite home all to yourself! Centrally Located, holiday rental in Winston Salem
Nice quite home all to yourself! Centrally Located, holiday rental in Winston Salem

Nice quite home all to yourself! Centrally Located

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out

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

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

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out

Beautiful apartment steps from Baptist Hospital in Central Winston-Salem

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out

Renovated 4 bedroom � - Walk to WFU!, holiday rental in Winston Salem
Renovated 4 bedroom � - Walk to WFU!, holiday rental in Winston Salem
Renovated 4 bedroom � - Walk to WFU!, holiday rental in Winston Salem

Renovated 4 bedroom � - Walk to WFU!

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 11
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out

Vintage Modern Synthesis in the Heart of Winston-Salem, holiday rental in Winston Salem
Vintage Modern Synthesis in the Heart of Winston-Salem, holiday rental in Winston Salem
Vintage Modern Synthesis in the Heart of Winston-Salem, holiday rental in Winston Salem

Vintage Modern Synthesis in the Heart of Winston-Salem

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out

Stylish 1BR Apt w/KING Bed in Central Location, holiday rental in Winston Salem
Stylish 1BR Apt w/KING Bed in Central Location, holiday rental in Winston Salem
Stylish 1BR Apt w/KING Bed in Central Location, holiday rental in Winston Salem

Stylish 1BR Apt w/KING Bed in Central Location

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out

Spacious 1BR w/ KING Bed Near Hospital & Downtown, holiday rental in Winston Salem
Spacious 1BR w/ KING Bed Near Hospital & Downtown, holiday rental in Winston Salem
Spacious 1BR w/ KING Bed Near Hospital & Downtown, holiday rental in Winston Salem

Spacious 1BR w/ KING Bed Near Hospital & Downtown

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out

Modern, Spacious 1 BR Apt Near Downtown/Hospital, holiday rental in Winston Salem
Modern, Spacious 1 BR Apt Near Downtown/Hospital, holiday rental in Winston Salem
Modern, Spacious 1 BR Apt Near Downtown/Hospital, holiday rental in Winston Salem

Modern, Spacious 1 BR Apt Near Downtown/Hospital

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out

Ardmore Home, holiday rental in Winston Salem
Ardmore Home, holiday rental in Winston Salem
Ardmore Home, holiday rental in Winston Salem

Ardmore Home

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out

Stylish 1BR Near Downtown & WFU Hospital, holiday rental in Winston Salem
Stylish 1BR Near Downtown & WFU Hospital, holiday rental in Winston Salem
Stylish 1BR Near Downtown & WFU Hospital, holiday rental in Winston Salem

Stylish 1BR Near Downtown & WFU Hospital

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out

Charming Cottage on Wooded Lot Close to Downtown, holiday rental in Winston Salem
Charming Cottage on Wooded Lot Close to Downtown, holiday rental in Winston Salem
Charming Cottage on Wooded Lot Close to Downtown, holiday rental in Winston Salem

Charming Cottage on Wooded Lot Close to Downtown

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out

3 bedroom/3 bath.. Nice quite home all to yourself! Centrally Located, holiday rental in Winston Salem
3 bedroom/3 bath.. Nice quite home all to yourself! Centrally Located, holiday rental in Winston Salem
3 bedroom/3 bath.. Nice quite home all to yourself! Centrally Located, holiday rental in Winston Salem

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

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection

Historical Bungalow Mins From Downtown, Shop, Hosp, holiday rental in Winston Salem
Historical Bungalow Mins From Downtown, Shop, Hosp, holiday rental in Winston Salem
Historical Bungalow Mins From Downtown, Shop, Hosp, holiday rental in Winston Salem

Historical Bungalow Mins From Downtown, Shop, Hosp

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 10
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out

Modern 1BR Near WFU Hospital, holiday rental in Winston Salem
Modern 1BR Near WFU Hospital, holiday rental in Winston Salem
Modern 1BR Near WFU Hospital, holiday rental in Winston Salem

Modern 1BR Near WFU Hospital

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out

Newly Renovated Apartment Only Steps from Wake Forest Hospital, holiday rental in Winston Salem
Newly Renovated Apartment Only Steps from Wake Forest Hospital, holiday rental in Winston Salem
Newly Renovated Apartment Only Steps from Wake Forest Hospital, holiday rental in Winston Salem

Newly Renovated Apartment Only Steps from Wake Forest Hospital

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out

� Gem Conv 2 WF Baptist/Novant Health/Hanes Mall Great for Medical Workers �, holiday rental in Winston Salem
� Gem Conv 2 WF Baptist/Novant Health/Hanes Mall Great for Medical Workers �, holiday rental in Winston Salem
� Gem Conv 2 WF Baptist/Novant Health/Hanes Mall Great for Medical Workers �, holiday rental in Winston Salem

� Gem Conv 2 WF Baptist/Novant Health/Hanes Mall Great for Medical Workers �

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out

Modern Downtown Retreat, holiday rental in Winston Salem
Modern Downtown Retreat, holiday rental in Winston Salem
Modern Downtown Retreat, holiday rental in Winston Salem

Modern Downtown Retreat

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out

New Luxury 1BR Near Downtown and Hospital, holiday rental in Winston Salem
New Luxury 1BR Near Downtown and Hospital, holiday rental in Winston Salem
New Luxury 1BR Near Downtown and Hospital, holiday rental in Winston Salem

New Luxury 1BR Near Downtown and Hospital

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out

New, modern guest apartment in perfect location!, holiday rental in Winston Salem
New, modern guest apartment in perfect location!, holiday rental in Winston Salem
New, modern guest apartment in perfect location!, holiday rental in Winston Salem

New, modern guest apartment in perfect location!

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out

2 BR Trendy Apt Walking Distance to Hospital, holiday rental in Winston Salem
2 BR Trendy Apt Walking Distance to Hospital, holiday rental in Winston Salem
2 BR Trendy Apt Walking Distance to Hospital, holiday rental in Winston Salem

2 BR Trendy Apt Walking Distance to Hospital

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out

NEW! Mid-Century Modern Cottage in Ardmore Area!, holiday rental in Winston Salem
NEW! Mid-Century Modern Cottage in Ardmore Area!, holiday rental in Winston Salem
NEW! Mid-Century Modern Cottage in Ardmore Area!, holiday rental in Winston Salem

NEW! Mid-Century Modern Cottage in Ardmore Area!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out

Sunlight facing entire Townhome 2 BR, 2.5 Bath, holiday rental in Winston Salem
Sunlight facing entire Townhome 2 BR, 2.5 Bath, holiday rental in Winston Salem
Sunlight facing entire Townhome 2 BR, 2.5 Bath, holiday rental in Winston Salem

Sunlight facing entire Townhome 2 BR, 2.5 Bath

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection

Classic 1963 Serro Scotty Camper, holiday rental in Winston Salem
Classic 1963 Serro Scotty Camper, holiday rental in Winston Salem
Classic 1963 Serro Scotty Camper, holiday rental in Winston Salem

Classic 1963 Serro Scotty Camper

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
Payment Protection

1BR Sparkling Clean Apartment, KING Bed, holiday rental in Winston Salem
1BR Sparkling Clean Apartment, KING Bed, holiday rental in Winston Salem
1BR Sparkling Clean Apartment, KING Bed, holiday rental in Winston Salem

1BR Sparkling Clean Apartment, KING Bed

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out

PreviousNext
123