Winston-Salem Vacation Rentals from CA $139: Short-Term Rentals for 2026

Q: 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! .

Check prices for these dates

In two weeks

In two months

In three months

In four months

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.

CA $170 total

includes taxes & fees

Nov 11 - Nov 12

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.

CA $273 total

includes taxes & fees

Nov 8 - Nov 9

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

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

Winston-Salem

Kara S.

CA $328 total

includes taxes & fees

Nov 8 - Nov 9

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

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

Winston-Salem

Allison T.

CA $440 total

includes taxes & fees

Dec 7 - Dec 8

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

5. 3 Mi to Dtwn Winston-Salem: Studio on Miller Park!

Winston-Salem

Anonymous traveller

CA $243 total

includes taxes & fees

Nov 10 - Nov 11

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

6. Quiet, newly renovated. Near everything!

Winston-Salem

Natalie K.

CA $354 total

includes taxes & fees

Nov 8 - Nov 9

7. La Casita .

Winston-Salem

Kristopher J.

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

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

Winston-Salem

Jessica R.

CA $283 total

includes taxes & fees

Nov 10 - Nov 11

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

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

Winston-Salem

Gerald

CA $392 total

includes taxes & fees

Nov 8 - Nov 9

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

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

Winston-Salem

Catherine D.

CA $545 total

includes taxes & fees

Nov 8 - Nov 9

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.

CA $384 total

includes taxes & fees

Nov 17 - Nov 18

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

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

Winston-Salem

Brittany

CA $387 total

includes taxes & fees

Nov 12 - Nov 13

A compact kitchen with a stainless steel refrigerator, an oven, and a microwave.

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

Winston-Salem

AJb b.

CA $428 total

includes taxes & fees

Nov 11 - Nov 12

A living room with a fireplace, a television, and a yellow armchair.

14. Historic West End Haven, walk to downtown Winston

Winston-Salem

Jacqueline B.

CA $671 total

includes taxes & fees

Nov 11 - Nov 12

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

15. Luxury 3BR Townhome - Sleep 6

Winston-Salem

Alyssa B.

CA $422 total

includes taxes & fees

Nov 30 - Dec 1

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

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

Winston-Salem

Jennifer

CA $356 total

includes taxes & fees

Nov 15 - Nov 16

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

17. The Hot Tub Hideaway

Winston-Salem

Alexandra M.

CA $358 total

includes taxes & fees

Nov 8 - Nov 9

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

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

Winston-Salem

Tatiana U.

CA $382 total

includes taxes & fees

Nov 8 - Nov 9

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

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

Winston-Salem

CA $475 total

includes taxes & fees

Nov 22 - Nov 23

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.

20. 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

CA $361 total

includes taxes & fees

Nov 18 - Nov 19

View all properties

Find vacation rentals that suit your style

Private vacation homes

Apartments

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

Quality Inn & Suites Hanes Mall

10/10 Excellent

"Very good for the price so I don't have any complaints"

Find out more about Winston-Salem

Everything you need to know about Winston-Salem vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winston-Salem vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winston-Salem vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Winston-Salem vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winston-Salem. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winston-Salem vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winston-Salem vacation rentals we have selected for you start as low as CA $139 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Winston-Salem rentals

At Expedia, we put the best Winston-Salem vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Winston-Salem rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winston-Salem vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winston-Salem. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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.

Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Winston-Salem vacation rentals

1. Updated 1BR cottage on private acre+ lot

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

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

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

5. 3 Mi to Dtwn Winston-Salem: Studio on Miller Park!

6. Quiet, newly renovated. Near everything!

7. La Casita .

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

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

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

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

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

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

14. Historic West End Haven, walk to downtown Winston

15. Luxury 3BR Townhome - Sleep 6

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

17. The Hot Tub Hideaway

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

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

20. Cozy 3BR Home Near Fairgrounds and Downtown

Find vacation rentals that suit your style

Top Winston-Salem Hotel Reviews

Quality Inn & Suites Hanes Mall

Red Roof Inn Winston-Salem

The Historic Brookstown Inn, Trademark Collection by Wyndham

Courtyard by Marriott Winston - Salem Downtown

Hampton Inn & Suites Winston-Salem Downtown

Kimpton Cardinal Hotel by IHG

Find out more about Winston-Salem

Frequently asked questions

Go further with the Expedia app