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

Winston-Salem Vacation Rentals

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Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

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, (30 reviews)
"The cottage was very cozy and clean, and the amenities provided were helpful! It was conveniently located for all the places we had to go and in a quiet neighborhood."
United States
Joanne A.
$123 nightly
The price is $139
Nov 2 - Nov 3
Total with taxes and fees
Updated 1BR cottage on private acre+ lot
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.

WEST END WHISPER 3 minute walk or drive to Everything. Prime location.
Winston-Salem
9.2 out of 10, Wonderful, (35 reviews)
"Lovely unit convenient to the theatre district and restaurants."
United States
Kelly N.
$133 nightly
The price is $150
Oct 25 - Oct 26
Total with taxes and fees
WEST END WHISPER 3 minute walk or drive to Everything. Prime location.
Outdoor dining

3. La Casita .

La Casita .
Winston-Salem
9.4 out of 10, Exceptional, (15 reviews)
"The location was perfect for what we needed."
United States
Giuliana
$167 nightly
The price is $188
Nov 3 - Nov 4
Total with taxes and fees
La Casita .
A yellow house with a red door, a brick chimney, and a front yard with small bushes.

4. 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, (27 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
$162 nightly
The price is $183
Nov 2 - Nov 3
Total with taxes and fees
3 Mi to Dtwn Winston-Salem: Studio on Miller Park!
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.
$183 nightly
The price is $207
Nov 3 - Nov 4
Total with taxes and fees
La Casita #2 Great location,close to downtown Winston Salem 1 mile from UNCSA
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

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
$243 nightly
The price is $258
Nov 15 - Nov 16
Total with taxes and fees
Chic 2BR/2BA Near Dining & Shops
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.

Log Cabin on Main St. In the ❤️ of Winston Salem. Sleeps 4 comfortably.
Winston-Salem
9.2 out of 10, Wonderful, (22 reviews)
"Cozy clean cabin, had trouble staying warm on the cool nights downstairs until we used the space heater. Altogether a very good stay."
United States
Tim W.
$254 nightly
The price is $287
Oct 21 - Oct 22
Total with taxes and fees
Log Cabin on Main St. In the ❤️ of Winston Salem. Sleeps 4 comfortably.
A covered porch with wooden flooring, black chairs, and hanging planters.

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

Cozy 2-bedroom bungalow in lovely Winston-Salem
Winston-Salem
10.0 out of 10, Exceptional, (43 reviews)
"Great place to stay we appreciate it being dog friendly"
United States
Melinda P.
$220 nightly
The price is $248
Oct 25 - Oct 26
Total with taxes and fees
Cozy 2-bedroom bungalow in lovely Winston-Salem
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.

9. 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
$244 nightly
The price is $261
Oct 21 - Oct 22
Total with taxes and fees
Cozy 3BR Home Near Fairgrounds and Downtown
A bedroom with a bed, bedside tables, a desk, and a chair. There is a window with curtains, a ceiling fan, and a wall-mounted lamp.

10. Charming 4-bedroom house in Winston-Salem near hospitals, downtown,universities

Charming 4-bedroom house in Winston-Salem near hospitals, downtown,universities
Winston-Salem
10.0 out of 10, Exceptional, (2 reviews)
"We had a wonderful stay here! The host was very welcoming and the house was clean and comfortable. Definitely recommend for anyone looking for a stay in the area!"
United States
Jen B.
$402 nightly
The price is $454
Oct 23 - Oct 24
Total with taxes and fees
Charming 4-bedroom house in Winston-Salem near hospitals, downtown,universities
A bedroom with a large bed, two bedside tables, a ceiling fan, and a window with curtains.

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

Man cave, Office, Soaking tub, & Firepit.
Winston-Salem
$341 nightly
The price is $385
Oct 26 - Oct 27
Total with taxes and fees
Man cave, Office, Soaking tub, & Firepit.
A modern kitchen with white cabinets, a black countertop, and a chandelier.

12. Quiet, newly renovated. Near everything!

Quiet, newly renovated. Near everything!
Winston-Salem
9.6 out of 10, Exceptional, (34 reviews)
"In town for work. Was a Great stay. Staying there again this week"
United States
Natalie K.
$226 nightly
The price is $255
Oct 25 - Oct 26
Total with taxes and fees
Quiet, newly renovated. Near everything!
A backyard with a fire pit, wicker furniture, a hot tub, and a hammock.

13. 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, (56 reviews)
"Enjoyable atmosphere, accommodating host, and a beautiful home overall. I’ll definitely plan another booking with them!"
United States
Brian Z.
$259 nightly
The price is $293
Oct 22 - Oct 23
Total with taxes and fees
Cozy King Blue H2O Staycation , Stock Tank Pool, Hot Tub, Fire Pit Pets OK!
A bedroom with a large window overlooking a forest. There is a bed with pillows and a wooden headboard.

14. The Hot Tub Hideaway

The Hot Tub Hideaway
Winston-Salem
9.6 out of 10, Exceptional, (38 reviews)
"What a beautiful cabin tucked away off the road. You’ll think you’re driving into a scary movie but then it opens up to the most beautiful view. Truly sleeping under the stars. Very clean cabin, would 100% stay again."
United States
Alyse P.
$238 nightly
The price is $269
Oct 22 - Oct 23
Total with taxes and fees
The Hot Tub Hideaway
A compact kitchen with white cabinets, a stainless steel refrigerator, a dining table with chairs, and a small potted plant.

15. La Casita #3

La Casita #3
Winston-Salem
$8,093 nightly
The price is $9,146
Oct 26 - Oct 27
Total with taxes and fees
La Casita #3
A modern kitchen with a wooden dining table, chairs, and a hanging light fixture.

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

Downtown Charm, 3 Bdr, Near Rest and Bars
Winston-Salem
9.4 out of 10, Exceptional, (29 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.
$290 nightly
The price is $311
Nov 3 - Nov 4
Total with taxes and fees
Downtown Charm, 3 Bdr, Near Rest and Bars
A small cabin surrounded by trees with a gravel path leading to it.

17. The Red Door Cabin

The Red Door Cabin
Winston-Salem
10.0 out of 10, Exceptional, (28 reviews)
"Cute place. "
United States
Sue C.
$238 nightly
The price is $269
Oct 26 - Oct 27
Total with taxes and fees
The Red Door Cabin
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.

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

Cozy Accessible Studio Near Wake Forest & Downtown Winston-Salem
Winston Salem
10.0 out of 10, Exceptional, (2 reviews)
"Great stay wonderful experience"
United States
dillon b.
$170 nightly
The price is $192
Nov 9 - Nov 10
Total with taxes and fees
Cozy Accessible Studio Near Wake Forest & Downtown Winston-Salem
A modern kitchen with white cabinets, stainless steel appliances, and a granite countertop.

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

New Build Clean Modern Sleep Luxuriously 4 min from Wake Forest University
Winston-Salem
10.0 out of 10, Exceptional, (7 reviews)
"We thoroughly enjoyed our stay; very nicely furnished, bed was comfortable and it was very clean and inviting, would not hesitate to rent again in the future"
United States
Catherine D.
$333 nightly
The price is $376
Oct 21 - Oct 22
Total with taxes and fees
New Build Clean Modern Sleep Luxuriously 4 min from Wake Forest University
A modern kitchen with stainless steel appliances, white cabinetry, and a wooden dining table.

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

Charming 2-bed, 2 full bath lower level studio with WiFi, AC in Ardmore
Winston-Salem
9.6 out of 10, Exceptional, (14 reviews)
"Host was very friendly - place was super clean and exactly as listed!"
United States
Brittany
$257 nightly
The price is $290
Nov 2 - Nov 3
Total with taxes and fees
Charming 2-bed, 2 full bath lower level studio with WiFi, AC in Ardmore
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.
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Top Winston-Salem Hotel Reviews

Kimpton Cardinal Hotel by IHG

Kimpton Cardinal Hotel by IHG

10/10 Excellent
"The restaurant on the property was incredible and staff was super friendly."
Martin 2-night trip
Posted 3 hours ago
Kimpton Cardinal Hotel by IHG

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 $139 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.

Explore a world of travel with Expedia

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.