Winston-Salem, NC Vacation Homes from ￥12,267

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Our top choices for Winston-Salem vacation homes

A small, single-story house with a front porch, surrounded by a garden with various plants and flowers.

1. Updated 1BR cottage on private acre+ lot

Winston-Salem

Dana A.

￥24,515 total

includes taxes & fees

Nov 22 - Nov 23

A white house number 28, a white door, a black mailbox, a black lantern, and a welcome mat.

2. Charming house in Washington Park, W-S, NC

Winston-Salem

Robert B.

￥25,127 total

includes taxes & fees

Nov 15 - Nov 16

3. La Casita .

Winston-Salem

Giuliana

￥29,237 total

includes taxes & fees

Dec 13 - Dec 14

A kitchen with granite countertops, a stainless steel sink, and a window with teal curtains.

4. Chic 2BR/2BA Near Dining & Shops

Winston-Salem

Jennifer

￥40,852 total

includes taxes & fees

Nov 15 - Nov 16

A modern kitchen with white subway tiles, stainless steel appliances, and grey cabinetry.

5. La Casita #2 Great location,close to downtown Winston Salem 1 mile from UNCSA

Winston-Salem

Jessica R.

￥32,227 total

includes taxes & fees

Nov 17 - Nov 18

A white house with a porch, large windows, and a staircase leading to the entrance.

6. Man cave, Office, Soaking tub, & Firepit.

Winston-Salem

￥56,319 total

includes taxes & fees

Nov 19 - Nov 20

A rustic wooden cabin with a porch, surrounded by greenery and a tree with pink flowers.

7. Log Cabin on Main St. In the ❤️ of Winston Salem. Sleeps 4 comfortably.

Winston-Salem

Hannah J.

￥43,457 total

includes taxes & fees

Nov 19 - Nov 20

A covered porch with wooden flooring, black chairs, and hanging planters.

8. Cozy 2-bedroom bungalow in lovely Winston-Salem

Winston-Salem

Kara S.

￥37,533 total

includes taxes & fees

Nov 15 - Nov 16

A living room with a beige sofa, a blue armchair, a coffee table, and a framed welcome sign.

9. Cozy 3BR Home Near Fairgrounds and Downtown

Winston-Salem

"Overall, we had a good stay. The home looked exactly like the photos and comfortably accommodated our group during a difficult time with family. The space was clean and met our needs. My only concerns were that the glass panel/door in the shower was missing, which made the bathroom less functional than expected. I also submitted a request to update the reservation to allow up to 5 guests because we had family and friends stopping by while we were grieving, but I never received a response from...

Jayceon

￥39,731 total

includes taxes & fees

Nov 16 - Nov 17

A compact kitchen with white cabinets, a stainless steel refrigerator, a dining table with chairs, and a small potted plant.

10. La Casita #3

Winston-Salem

￥1,386,168 total

includes taxes & fees

Nov 17 - Nov 18

A kitchen with a black sink, a window above it, and various bottles on the counter.

11. Quiet, newly renovated. Near everything!

Winston-Salem

Natalie K.

￥38,637 total

includes taxes & fees

Nov 16 - Nov 17

A backyard with a circular hot tub, wicker furniture, and a hammock.

12. Cozy King Blue H2O Staycation , Stock Tank Pool, Hot Tub, Fire Pit Pets OK!

Winston-Salem

Gerald

￥42,327 total

includes taxes & fees

Dec 13 - Dec 14

A wooden deck with two blue chairs and a table, surrounded by a wooden railing and dense greenery.

13. Luxury 3BR Townhome - Sleep 6

Winston-Salem

Alyssa B.

￥46,740 total

includes taxes & fees

Dec 8 - Dec 9

A two-story house with a porch, a yellow door, and a stone foundation.

14. Downtown Charm, 3 Bdr, Near Rest and Bars

Winston-Salem

Allison T.

￥49,883 total

includes taxes & fees

Dec 7 - Dec 8

A wooden deck with wicker furniture and a glass coffee table.

15. New Build Clean Modern Sleep Luxuriously 4 min from Wake Forest University

Winston-Salem

Catherine D.

￥61,574 total

includes taxes & fees

Nov 22 - Nov 23

A house with a concrete driveway, a wooden deck, and a well-lit front porch.

16. 4 Beds | King | 85” TV | 5min to WSSU & Downtown

Winston-Salem

Anonymous traveler

A modern kitchen with a large island, bar stools, and pendant lighting.

17. La Casita: A Cozy Retreat Near Wake Forest University"

Winston-Salem

Melissa T.

￥43,150 total

includes taxes & fees

Nov 16 - Nov 17

A wooden cabin with a covered porch, a front door, and a 'Welcome' sign.

18. Winston Salem 3Bd 2Ba GAME ROOM mins to Downtown

Winston-Salem

AJb b.

￥51,120 total

includes taxes & fees

Nov 22 - Nov 23

A backyard with a barbecue grill, a fire pit, and wooden deck seating.

19. Private Hot Tub Retreat | King Bed | Outdoor Oasis

Winston-Salem

Karl R.

￥58,009 total

includes taxes & fees

Nov 19 - Nov 20

A covered porch with two wicker chairs and a small table, a brick wall, and a view of a street and trees.

20. Recently renovated luxury duplex unit. Short walk to Atrium WF Baptist Hospital!

Winston-Salem

Tatiana U.

￥45,036 total

includes taxes & fees

Nov 15 - Nov 16

View all properties

Learn more about Winston-Salem

Explore Old Salem's living history museum where costumed interpreters demonstrate crafts and daily life from the 1700s. Discover the city's artistic side at Reynolda House, featuring American art within the historic estate of tobacco magnate R.J. Reynolds.

See all hotels in Winston-Salem

A cityscape with a mix of modern and historic buildings, a prominent dome-shaped skyscraper, and a dense residential area with trees.

Top reviews in Winston-Salem

A covered porch with brick columns, outdoor seating, and a well-maintained garden with pink flowers.

Summit Street Inns

Winston-Salem

10/10 Excellent

Cynthia

A brick building with a sign for Brookstown Mill, a bench, and directional signs for nearby locations.

The Historic Brookstown Inn, Trademark Collection by Wyndham

Winston-Salem

10/10 Excellent

Didn’t realize when I booked but the location had a complementary wine tasting. Everyone who went to it was sooo personable. Normally not my scene, but everyone was so welcoming. Great breakfast spread too. The area is very walkable. I took a nearby path and ended up at Salem College very close by. It is America’s oldest women’s college dating back to colonial times. Many of the buildings look that old, but are very well kept. Just a beautiful experience all around. Clean rooms too!

Nicholas

A well-lit, spacious lobby with leather seating, a piano, and a view of the outdoors through large windows.

O.Henry Hotel

Greensboro

10/10 Excellent

I use to live in Greensboro for many many years and always thought this looked like a fun place to stay. I have eaten at the green valley grill but had never had the pleasure of staying at the o’Henry. I was in town for a night decided to stay here. The hotel is gorgeous. The room is spacious! It is very elegant and classy..reminiscent of “old money”. I would stay again if ever given the opportunity

Alicia

A spacious lobby with a central seating area, large windows, and a view of greenery outside.

Proximity Hotel

Greensboro

10/10 Excellent

We stayed at the "sister property" (the O'Henry) several times but had not stayed at the Proximity. We tried but COVID or one thing or another led to not making our trip. We had met the original owners and then knew about their transfer to the employees. What a terrific thing for an employer to do and what a great deal for the employees. It appears that they are doing a good job and keeping the quality up to former standards. The decor and amenities are outstanding, the Bistro not only has...

James