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

Winston-Salem Vacation Rentals

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! .

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November 2026

December 2026

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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.

$136 nightly

Nov 22 - Nov 23

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 12 - Nov 13

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

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

Winston-Salem

Robert B.

$140 nightly

Nov 12 - Nov 13

Total with taxes and fees

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

6. The Red Door Cabin

Winston-Salem

Sue C.

$208 nightly

Nov 12 - Nov 13

Total with taxes and fees

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

Winston-Salem

Jennifer

$242 nightly

Nov 15 - Nov 16

Total with taxes and fees

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

8. The Hot Tub Hideaway

Winston-Salem

Alexandra M.

$208 nightly

Nov 12 - Nov 13

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

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

Winston-Salem

$314 nightly

Nov 19 - Nov 20

Total with taxes and fees

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

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

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

13. Quiet, newly renovated. Near everything!

Winston-Salem

Natalie K.

$217 nightly

Nov 12 - Nov 13

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.

14. 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

$234 nightly

Nov 16 - Nov 17

Total with taxes and fees

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

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

Winston-Salem

Brittany

$262 nightly

Nov 18 - Nov 19

Total with taxes and fees

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

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

Winston-Salem

Allison T.

$293 nightly

Dec 7 - Dec 8

Total with taxes and fees

A bedroom with a bed, bedside lamps, a chair, an ottoman, a window with curtains, an air conditioning unit, and a mirror on the wall.

17. Cozy Accessible Studio Near Wake Forest & Downtown Winston-Salem

Winston Salem

dillon b.

$159 nightly

Dec 1 - Dec 2

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.

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

Winston-Salem

Tatiana U.

$251 nightly

Nov 12 - Nov 13

Total with taxes and fees

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

19. La Casita #3

Winston-Salem

$7,330 nightly

Nov 16 - Nov 17

Total with taxes and fees

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

20. 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

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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 restaurant interior with high ceilings, exposed brick walls, and a mix of seating arrangements including tables and booths.

Springhill Suites By Marriott High Point Downtown

High Point

10/10 Excellent

This is a relatively new hotel in downtown High Point, right near the minor league baseball stadium and few restaurants. It's only 5 minutes from High Point University which was very convenient. The entire staff was beyond friendly and helpful, thank you for an enjoyable stay!! The hotel was extremely clean and safe. I loved all the different areas to gather and socialize in the lobby and outdoor spaces. I will definitely stay again.

Michael

A modern building with a covered entrance, brick walls, and large windows.

Holiday Inn Express & Suites Winston Salem Sw Clemmons by IHG

Clemmons

10/10 Excellent

Duane

A breakfast buffet area with various food items and a sign that reads "HAPPY BREAKFAST STARTS HERE".

Hampton Inn Winston-Salem Hanes Mall

Winston-Salem

10/10 Excellent

Christy

A hotel with a modern design, featuring a brick facade and a well-lit entrance.

SpringHill Suites by Marriott Greensboro Airport

Greensboro

10/10 Excellent

Jason

An indoor swimming pool with four lounge chairs and a metal ladder.

Holiday Inn Express and Suites Kernersville South by IHG

Kernersville

10/10 Excellent

Charles Richard

A modern bar area with a marble countertop, purple bar stools, and a large chandelier.

Hampton Inn & Suites Winston-Salem Downtown

Winston-Salem

10/10 Excellent

Jesse

A grand lobby with a central fountain, multiple staircases, and elegant chandeliers.

Grandover Resort & Spa, a Wyndham Grand Hotel

Sedgefield

10/10 Excellent

Risa

A modern restaurant with a long communal table, booths, and individual tables.

Hampton Inn & Suites Winston-Salem/University Area, NC

Winston-Salem

10/10 Excellent

Destane

A Holiday Inn hotel with a modern design, featuring a prominent entrance and a well-lit facade.

Holiday Inn Greensboro Coliseum by IHG

Greensboro

10/10 Excellent

John

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, condos, resorts, cabins, villas, motels. 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 low season months. For more hustle and bustle, you may prefer to visit Winston-Salem in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $153 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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.

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