Winston - Salem Vacation Rentals from $46: Search Short-Term Rentals

A cityscape at dusk with prominent buildings like the Winston Tower and a modern skyscraper.

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Our top choices for Winston - Salem vacation rentals

A kitchen with white cabinets, a granite countertop, a stove, and a microwave. There is a hanging light fixture and a window with blinds.

1. Updated 1BR cottage on private acre+ lot

Winston-Salem

Dana A.

$134 nightly

Nov 23 - Nov 24

Total with taxes and fees

A modern kitchen with white cabinets, a stainless steel dishwasher, and a granite countertop.

2. WEST END WHISPER 3 minute walk or drive to Everything. Prime location.

Winston-Salem

Jayden J.

$175 nightly

Nov 15 - Nov 16

Total with taxes and fees

A yellow house with a red door, a brick chimney, and a front yard with small bushes.

3. 3 Mi to Dtwn Winston-Salem: Studio on Miller Park!

Winston-Salem

Britt D.

$153 nightly

Nov 22 - Nov 23

Total with taxes and fees

4. La Casita .

Winston-Salem

Giuliana

$168 nightly

Dec 8 - Dec 9

Total with taxes and fees

A hotel room with a bed, a chair, a window, a mirror, and a door.

5. Kernersville NC | Queen Bed|Smk

Kernersville NC

Anonymous traveler

$42 nightly

Nov 17 - Nov 18

Total with taxes and fees

A spacious kitchen with a granite countertop, a sink, and a dining area with a long table and chairs.

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

Winston-Salem

Jennifer

$242 nightly

Dec 1 - Dec 2

Total with taxes and fees

A small cabin surrounded by trees with a gravel path leading to it.

7. The Red Door Cabin

Winston-Salem

Sue C.

$225 nightly

Nov 15 - Nov 16

Total with taxes and fees

A living room with a sofa, armchair, coffee table, and a small side table.

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

Winston-Salem

Robert B.

$140 nightly

Nov 15 - Nov 16

Total with taxes and fees

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

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

Winston-Salem

Kara S.

$208 nightly

Nov 15 - Nov 16

Total with taxes and fees

A modern kitchen with white cabinets, a stainless steel refrigerator, and a marble backsplash. There are two bar stools and a wooden dining table with chairs.

10. 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

$238 nightly

Nov 16 - Nov 17

Total with taxes and fees

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

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

Winston-Salem

Hannah J.

$242 nightly

Nov 17 - Nov 18

Total with taxes and fees

A bedroom with a large window overlooking a forest. There is a bed with pillows and a wooden headboard.

12. The Hot Tub Hideaway

Winston-Salem

Alexandra M.

$226 nightly

Nov 17 - Nov 18

Total with taxes and fees

A modern kitchen with a wooden dining table, chairs, and a hanging light fixture.

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

Winston-Salem

Allison T.

$294 nightly

Dec 7 - Dec 8

Total with taxes and fees

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

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

Winston-Salem

Jessica R.

$179 nightly

Nov 17 - Nov 18

Total with taxes and fees

A modern kitchen with white cabinets, a black countertop, and a chandelier.

15. Quiet, newly renovated. Near everything!

Winston-Salem

Natalie K.

$217 nightly

Nov 15 - Nov 16

Total with taxes and fees

A dining area with a large table, chairs, and a view into a kitchen and dining room.

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

Winston-Salem

$315 nightly

Nov 19 - Nov 20

Total with taxes and fees

A modern kitchen with stainless steel appliances, white cabinetry, and a wooden dining table.

17. Charming 2-bed, 2 full bath lower level studio with WiFi, AC in Ardmore

Winston-Salem

Brittany

$262 nightly

Nov 22 - Nov 23

Total with taxes and fees

A kitchen with white cabinets, a granite countertop, and a black stove.

18. Cute cottage in a rural setting

Clemmons

Seli J.

$253 nightly

Nov 14 - Nov 15

Total with taxes and fees

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

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

Winston-Salem

Gerald

$236 nightly

Nov 16 - Nov 17

Total with taxes and fees

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.

$251 nightly

Nov 15 - Nov 16

Total with taxes and fees

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Find vacation rentals that suit your style

Top Winston - Salem Hotel Reviews

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 courtyard with brick buildings, a staircase, and potted plants.

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 courtyard with outdoor seating, a fountain, and lush greenery.

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 indoor area with multiple dining tables and chairs, a central staircase, and large windows allowing natural light.

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

A large dome-shaped tent with a deck and seating area, surrounded by dense forest and a mountain in the background.

Pilot Mountain Glamping Resort

Pinnacle

10/10 Excellent

We really enjoyed our stay at Pilot Mountain Glamping Resort. The space was comfortable, beautifully designed inside and out, and very clean. It felt like the hosts had thought of everything guests might need to feel at home. Being so close to the Pilot Mountain trails was especially convenient after a long hike. The location right by the road made it easy to get to, though the traffic noise was quite loud. That was the only downside for us. Overall, we had a lovely stay.

Ayla