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Holiday Rentals in Winston Salem

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5 km
265 rentals in Winston Salem.
The James Bond Hidden Cottage By Wake Forest U & Downtown - Smashing Location, holiday rental in Winston Salem
The James Bond Hidden Cottage By Wake Forest U & Downtown - Smashing Location, holiday rental in Winston Salem
The James Bond Hidden Cottage By Wake Forest U & Downtown - Smashing Location, holiday rental in Winston Salem

The James Bond Hidden Cottage By Wake Forest U & Downtown - Smashing Location

95 reviews
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
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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

49 reviews
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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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

110 reviews
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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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

68 reviews
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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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

64 reviews
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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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

41 reviews
Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
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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

56 reviews
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Walking distance to Reynolda House and Gardens. Close to Wake Forest University, holiday rental in Winston Salem
Walking distance to Reynolda House and Gardens. Close to Wake Forest University, holiday rental in Winston Salem
Walking distance to Reynolda House and Gardens. Close to Wake Forest University, holiday rental in Winston Salem

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

60 reviews
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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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

23 reviews
Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
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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

32 reviews
Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
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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

60 reviews
Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
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✨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✨

20 reviews
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
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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

21 reviews
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
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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

18 reviews
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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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

34 reviews
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Deacon Stays: The Brookwood - Walk to WFU, holiday rental in Winston Salem
Deacon Stays: The Brookwood - Walk to WFU, holiday rental in Winston Salem
Deacon Stays: The Brookwood - Walk to WFU, holiday rental in Winston Salem

Deacon Stays: The Brookwood - Walk to WFU

11 reviews
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 11
Match: Sleeps
More info
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La Casita!! COZY, CHARMING near to WFU, holiday rental in Winston Salem
La Casita!! COZY, CHARMING near to WFU, holiday rental in Winston Salem
La Casita!! COZY, CHARMING near to WFU, holiday rental in Winston Salem

La Casita!! COZY, CHARMING near to WFU

21 reviews
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Updated Hidden Gem Close to Winston/Kernersville, holiday rental in Winston Salem
Updated Hidden Gem Close to Winston/Kernersville, holiday rental in Winston Salem
Updated Hidden Gem Close to Winston/Kernersville, holiday rental in Winston Salem

Updated Hidden Gem Close to Winston/Kernersville

33 reviews
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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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.

14 reviews
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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Wake Forest University, Coliseum, Downtown, Convention Center Area, holiday rental in Winston Salem
Wake Forest University, Coliseum, Downtown, Convention Center Area, holiday rental in Winston Salem
Wake Forest University, Coliseum, Downtown, Convention Center Area, holiday rental in Winston Salem

Wake Forest University, Coliseum, Downtown, Convention Center Area

15 reviews
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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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!

8 reviews
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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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

15 reviews
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Cozy guest suite in Winston Salem, holiday rental in Winston Salem
Cozy guest suite in Winston Salem, holiday rental in Winston Salem
Cozy guest suite in Winston Salem, holiday rental in Winston Salem

Cozy guest suite in Winston Salem

18 reviews
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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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

12 reviews
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Elegant Pet Friendly Ranch Home close to everything!, holiday rental in Winston Salem
Elegant Pet Friendly Ranch Home close to everything!, holiday rental in Winston Salem
Elegant Pet Friendly Ranch Home close to everything!, holiday rental in Winston Salem

Elegant Pet Friendly Ranch Home close to everything!

7 reviews
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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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

16 reviews
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Bright & Breezy near UNCSA & Downtown, holiday rental in Winston Salem
Bright & Breezy near UNCSA & Downtown, holiday rental in Winston Salem
Bright & Breezy near UNCSA & Downtown, holiday rental in Winston Salem

Bright & Breezy near UNCSA & Downtown

11 reviews
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Walk to Wake Forest University, holiday rental in Winston Salem
Walk to Wake Forest University, holiday rental in Winston Salem
Walk to Wake Forest University, holiday rental in Winston Salem

Walk to Wake Forest University

12 reviews
Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
More info
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Pool, Custom Mid Century Gem, walk to Wake Forest University, Reynolda House, holiday rental in Winston Salem
Pool, Custom Mid Century Gem, walk to Wake Forest University, Reynolda House, holiday rental in Winston Salem
Pool, Custom Mid Century Gem, walk to Wake Forest University, Reynolda House, holiday rental in Winston Salem

Pool, Custom Mid Century Gem, walk to Wake Forest University, Reynolda House

5 reviews
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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The Blue Door Cabin, holiday rental in Winston Salem
The Blue Door Cabin, holiday rental in Winston Salem
The Blue Door Cabin, holiday rental in Winston Salem

The Blue Door Cabin

5 reviews
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
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Governors Club Studio Apartment in Prestigious Buena Vista, holiday rental in Winston Salem
Governors Club Studio Apartment in Prestigious Buena Vista, holiday rental in Winston Salem
Governors Club Studio Apartment in Prestigious Buena Vista, holiday rental in Winston Salem

Governors Club Studio Apartment in Prestigious Buena Vista

10 reviews
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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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

11 reviews
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Renovated 1BR Apartment Steps from WFU Hospital, holiday rental in Winston Salem
Renovated 1BR Apartment Steps from WFU Hospital, holiday rental in Winston Salem
Renovated 1BR Apartment Steps from WFU Hospital, holiday rental in Winston Salem

Renovated 1BR Apartment Steps from WFU Hospital

7 reviews
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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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

7 reviews
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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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!

7 reviews
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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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

7 reviews
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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★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

10 reviews
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Ardmore Home, holiday rental in Winston Salem
Ardmore Home, holiday rental in Winston Salem
Ardmore Home, holiday rental in Winston Salem

Ardmore Home

18 reviews
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Rustic Loft in Downtown Arts District, holiday rental in Winston Salem
Rustic Loft in Downtown Arts District, holiday rental in Winston Salem
Rustic Loft in Downtown Arts District, holiday rental in Winston Salem

Rustic Loft in Downtown Arts District

6 reviews
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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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

8 reviews
Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 10
Match: Sleeps
More info
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Gorgeous Downtown Getaway! Minutes From The City!, holiday rental in Winston Salem
Gorgeous Downtown Getaway! Minutes From The City!, holiday rental in Winston Salem
Gorgeous Downtown Getaway! Minutes From The City!, holiday rental in Winston Salem

Gorgeous Downtown Getaway! Minutes From The City!

10 reviews
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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� 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 �

7 reviews
Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
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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

4 reviews
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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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

4 reviews
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Classy 1BR Steps from WF Hospital - Free Parking, holiday rental in Winston Salem
Classy 1BR Steps from WF Hospital - Free Parking, holiday rental in Winston Salem
Classy 1BR Steps from WF Hospital - Free Parking, holiday rental in Winston Salem

Classy 1BR Steps from WF Hospital - Free Parking

4 reviews
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Walking Distance To The Mall, Park, Food, Hospital, holiday rental in Winston Salem
Walking Distance To The Mall, Park, Food, Hospital, holiday rental in Winston Salem
Walking Distance To The Mall, Park, Food, Hospital, holiday rental in Winston Salem

Walking Distance To The Mall, Park, Food, Hospital

4 reviews
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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Historic West End Hideaway, walk to downtown WS, holiday rental in Winston Salem
Historic West End Hideaway, walk to downtown WS, holiday rental in Winston Salem
Historic West End Hideaway, walk to downtown WS, holiday rental in Winston Salem

Historic West End Hideaway, walk to downtown WS

4 reviews
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
More info
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1BR Fully Outfitted Apt with Central Location, holiday rental in Winston Salem
1BR Fully Outfitted Apt with Central Location, holiday rental in Winston Salem
1BR Fully Outfitted Apt with Central Location, holiday rental in Winston Salem

1BR Fully Outfitted Apt with Central Location

3 reviews
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Historic Victorian Home - 2 BR Apartment - Downtown Winston-Salem, holiday rental in Winston Salem
Historic Victorian Home - 2 BR Apartment - Downtown Winston-Salem, holiday rental in Winston Salem
Historic Victorian Home - 2 BR Apartment - Downtown Winston-Salem, holiday rental in Winston Salem

Historic Victorian Home - 2 BR Apartment - Downtown Winston-Salem

3 reviews
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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2 Bedroom, 2 Bathroom in Downtown Winston-Salem, holiday rental in Winston Salem
2 Bedroom, 2 Bathroom in Downtown Winston-Salem, holiday rental in Winston Salem
2 Bedroom, 2 Bathroom in Downtown Winston-Salem, holiday rental in Winston Salem

2 Bedroom, 2 Bathroom in Downtown Winston-Salem

1 review
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
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