A cityscape with various buildings, including a prominent skyscraper and several mid-rise structures.

Winston-Salem Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

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

Updated 1BR cottage on private acre+ lot
Winston-Salem
10.0 out of 10, Exceptional, (31 reviews)
"Lovely and charming place to stay. Really enjoyed my time there."
United States
Dana A.
The price is ￥9,248
￥19,526 total
includes taxes & fees
Nov 11 - Nov 12
Updated 1BR cottage on private acre+ lot
A backyard with a fire pit, wicker furniture, a hot tub, and a hammock.

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

Cozy King Blue H2O Staycation , Stock Tank Pool, Hot Tub, Fire Pit Pets OK!
Winston-Salem
9.6 out of 10, Exceptional, (57 reviews)
"Fantasticly cozy as advertised and wonderful!"
United States
Gerald
The price is ￥26,625
￥44,056 total
includes taxes & fees
Nov 8 - Nov 9
Cozy King Blue H2O Staycation , Stock Tank Pool, Hot Tub, Fire Pit Pets OK!
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!

3 Mi to Dtwn Winston-Salem: Studio on Miller Park!
Winston-Salem
9.8 out of 10, Exceptional, (28 reviews)
"What a cute and very clean place to stay! The room is located right at a beautiful park with a walking/running path and wooded trails. Shops are very close by and the neighborhood is cute and safe. Would definitely stay here again. "
United States
Anonymous traveler
The price is ￥10,460
￥27,400 total
includes taxes & fees
Nov 10 - Nov 11
3 Mi to Dtwn Winston-Salem: Studio on Miller Park!
A modern kitchen with white cabinets, a stainless steel dishwasher, and a granite countertop.

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

WEST END WHISPER 3 minute walk or drive to Everything. Prime location.
Winston-Salem
9.4 out of 10, Exceptional, (37 reviews)
"Property was amazing, clean, and well priced."
United States
Jayden J.
The price is ￥17,009
￥31,145 total
includes taxes & fees
Nov 17 - Nov 18
WEST END WHISPER 3 minute walk or drive to Everything. Prime location.
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

La Casita #2 Great location,close to downtown Winston Salem 1 mile from UNCSA
Winston-Salem
10.0 out of 10, Exceptional, (3 reviews)
"Quiet area, cozy rooms and good location. Loved staying here!"
United States
Jessica R.
The price is ￥15,025
￥32,105 total
includes taxes & fees
Nov 10 - Nov 11
La Casita #2 Great location,close to downtown Winston Salem 1 mile from UNCSA
A covered porch with wooden flooring, black chairs, and hanging planters.

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

Cozy 2-bedroom bungalow in lovely Winston-Salem
Winston-Salem
10.0 out of 10, Exceptional, (45 reviews)
"We had a great time!"
United States
Kara S.
The price is ￥18,685
￥37,230 total
includes taxes & fees
Nov 8 - Nov 9
Cozy 2-bedroom bungalow in lovely Winston-Salem
A spacious kitchen with a granite countertop, a sink, and a dining area with a long table and chairs.

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

Chic 2BR/2BA Near Dining & Shops
Winston-Salem
9.6 out of 10, Exceptional, (17 reviews)
"Clean, well located, good value, comfortable beds."
United States
Jennifer
Chic 2BR/2BA Near Dining & Shops
A compact kitchen with white cabinets, a stainless steel refrigerator, a dining table with chairs, and a small potted plant.

8. La Casita #3

La Casita #3
Winston-Salem
The price is ￥13,040
￥1,367,971 total
includes taxes & fees
Nov 10 - Nov 11
La Casita #3
A modern kitchen with a central island, stainless steel appliances, and wooden bar stools.

9. New Build 3BR by Wake Forest | Pets OK, Sleeps 6

New Build 3BR by Wake Forest | Pets OK, Sleeps 6
Winston-Salem
The price is ￥14,453
￥46,954 total
includes taxes & fees
Nov 9 - Nov 10
New Build 3BR by Wake Forest | Pets OK, Sleeps 6
A bedroom with a large window overlooking a forest. There is a bed with pillows and a wooden headboard.

10. The Hot Tub Hideaway

The Hot Tub Hideaway
Winston-Salem
9.6 out of 10, Exceptional, (38 reviews)
"This place is beautiful! Truly a hidden gem! Perfect little get away for a couple. Spent a 3 day weekend with my bf and dog and it couldn’t have been more peaceful! Shared the listing for this vrbo with multiple friends and family because of how much I loved my stay. Will definitely book again."
United States
Alexandra M.
The price is ￥22,678
￥37,624 total
includes taxes & fees
Nov 9 - Nov 10
The Hot Tub Hideaway
A modern kitchen with white cabinets, a black countertop, and a chandelier.

11. Quiet, newly renovated. Near everything!

Quiet, newly renovated. Near everything!
Winston-Salem
9.6 out of 10, Exceptional, (35 reviews)
"In town for work. Was a Great stay. Staying there again this week"
United States
Natalie K.
The price is ￥18,269
￥38,443 total
includes taxes & fees
Nov 8 - Nov 9
Quiet, newly renovated. Near everything!
A dining area with a large table, chairs, and a view into a kitchen and dining room.

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

Man cave, Office, Soaking tub, & Firepit.
Winston-Salem
Man cave, Office, Soaking tub, & Firepit.
A small cabin surrounded by trees with a gravel path leading to it.

13. The Red Door Cabin

The Red Door Cabin
Winston-Salem
10.0 out of 10, Exceptional, (29 reviews)
"Cute place. "
United States
Sue C.
The price is ￥22,537
￥37,034 total
includes taxes & fees
Nov 8 - Nov 9
The Red Door Cabin
A rustic wooden cabin with a porch, surrounded by greenery and a tree with pink flowers.

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

Log Cabin on Main St. In the ❤️ of Winston Salem. Sleeps 4 comfortably.
Winston-Salem
9.2 out of 10, Wonderful, (22 reviews)
"Wonderful stay! "
United States
Hannah J.
The price is ￥19,541
￥43,392 total
includes taxes & fees
Nov 17 - Nov 18
Log Cabin on Main St. In the ❤️ of Winston Salem. Sleeps 4 comfortably.
A modern kitchen with a large island, bar stools, and pendant lighting.

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

La Casita: A Cozy Retreat Near Wake Forest University"
Winston-Salem
9.6 out of 10, Exceptional, (62 reviews)
"This is a great place. Clean, updated, close to wake Forest U and the host was perfect - highly recommend."
United States
Melissa T.
The price is ￥18,111
￥43,601 total
includes taxes & fees
Dec 3 - Dec 4
La Casita: A Cozy Retreat Near Wake Forest University"
A living room with a sofa, armchair, coffee table, and a small side table.

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

Charming house in Washington Park, W-S, NC
Winston-Salem
10.0 out of 10, Exceptional, (1 review)
"Good location. The beds are exceptionally comfortable. Had a small issue with the couch but he came right over to fix it"
Canada
Robert B.
Charming house in Washington Park, W-S, NC
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.

17. Cozy 3BR Home Near Fairgrounds and Downtown

Cozy 3BR Home Near Fairgrounds and Downtown
Winston-Salem
8.0 out of 10, Very good, (1 review)
"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...
United States
Jayceon
The price is ￥15,690
￥37,467 total
includes taxes & fees
Nov 8 - Nov 9
Cozy 3BR Home Near Fairgrounds and Downtown
A house with a concrete driveway, a wooden deck, and a well-lit front porch.

18. 4 Beds | King | 85” TV | 5min to WSSU & Downtown

4 Beds | King | 85” TV | 5min to WSSU & Downtown
Winston-Salem
9.0 out of 10, Wonderful, (4 reviews)
"We enjoyed our short stay, house is very cute and cozy and well put together "
United States
Anonymous traveler
4 Beds | King | 85” TV | 5min to WSSU & Downtown
A modern kitchen with wooden cabinets, a built-in microwave, and a large island.

19. Charming 2-bedroom cabin with WiFi in brilliant Winston-Salem

Charming 2-bedroom cabin with WiFi in brilliant Winston-Salem
Winston-Salem
9.6 out of 10, Exceptional, (14 reviews)
"We loved this little cabin! Would definitely recommend!"
United States
Kathryn P.
The price is ￥22,537
￥39,173 total
includes taxes & fees
Nov 10 - Nov 11
Charming 2-bedroom cabin with WiFi in brilliant Winston-Salem
A modern kitchen with a wooden dining table, chairs, and a hanging light fixture.

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

Downtown Charm, 3 Bdr, Near Rest and Bars
Winston-Salem
9.4 out of 10, Exceptional, (30 reviews)
"My husband and I had a wonderful 2-night stay here. The property was incredibly clean and located in a very quiet neighborhood. It was the perfect amount of space for the two of us. We would definitely stay here again!""
United States
Allison T.
Downtown Charm, 3 Bdr, Near Rest and Bars
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winston-Salem Hotel Reviews

Holiday Inn Express Winston-Salem Medical Center Area by IHG

Holiday Inn Express Winston-Salem Medical Center Area by IHG

10/10 Excellent
"Very Clean. Kind and helpful staff. Great location."
Chakia 2-night trip
Posted 20 hours ago
Holiday Inn Express Winston-Salem Medical Center Area by IHG

Find out more about Winston-Salem

Search for holiday rentals in Winston-Salem on Expedia! You can easily find your home rentals, villas, holiday apartments in Winston-Salem using one of the methods below:

  • View our selection of featured holiday rentals in Winston-Salem
  • Use the map to find apartments and other holiday homes in the Winston-Salem neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Winston-Salem while they last

Look no further and take a look at our great range of rental properties in Winston-Salem!

Frequently asked questions

Can I find vacation rentals in Winston-Salem?

Yes, there are vacation rentals in Winston-Salem close to Salem College Elberson Fine Arts Center, or you can go with a more secluded option if you'd like a relaxing place to stay. Visitors like the array of shops and lush forest in Winston-Salem. Make sure to also enjoy the college campus and top-notch restaurants during your vacation.

What are some of the best vacation rentals that Winston-Salem has to offer?

Arcade Kid Friendly Firepit Grill HotTub: This highly rated vacation home rental in Winston-Salem is located near the airport and has a fireplace, a private balcony, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation. Other favorite homes for rent in Winston-Salem are Cozy 2-bedroom bungalow in lovely Winston-Salem and Quiet, newly renovated. Near everything!.

How many vacation rentals will I find in Winston-Salem?

Choose from 210 Expedia vacation rentals in Winston-Salem for a memorable vacation.

What can I see and do in Winston-Salem?

Enjoy the outdoors at Reynolda Gardens and Salem Lake, or simply take in cultural attractions like Old Salem and Reynolda House Museum of American Art. Truist Stadium and Bowman Gray Stadium are other places to visit while you're in town.

What are vacation rentals like in Winston-Salem?

Vacation rentals are privately owned properties you can book for several days or longer in Winston-Salem. Vacation rentals feature amenities such as patios, hot tubs, and fire pits so you'll have everything you want. If you're concerned about a sanitized environment, a vacation rental can offer a sense of privacy away from public hotel elevators and busy reception areas while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a hotel, which is another reason why a vacation rental is an attractive option for family gatherings.