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
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Winston-Salem vacation rentals

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

1. The Ardmore Executive Suite

The Ardmore Executive Suite
4.0 star property
Winston-Salem
7.6 out of 10, Good, (5 reviews)
"Place was wonderful. Host was great. No complaints at all."
United States
Jean
$168 nightly
The price is $190
Oct 4 - Oct 5
Total with taxes and fees
The Ardmore Executive Suite
A kitchen with white cabinets, a granite countertop, a stove, and a microwave. There is a hanging light fixture and a window with blinds.

2. Updated 1BR cottage on private acre+ lot

Updated 1BR cottage on private acre+ lot
Winston-Salem
10.0 out of 10, Exceptional, (29 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.
$117 nightly
The price is $132
Oct 6 - Oct 7
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.

3. 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, (33 reviews)
"The host was very nice and understanding it was great to find a place pet friendly MollyAnn enjoyed her stay. "
United States
Taya S.
$133 nightly
The price is $150
Oct 4 - Oct 5
Total with taxes and fees
WEST END WHISPER 3 minute walk or drive to Everything. Prime location.
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
$161 nightly
The price is $182
Oct 4 - Oct 5
Total with taxes and fees
3 Mi to Dtwn Winston-Salem: Studio on Miller Park!
Outdoor dining

5. La Casita .

La Casita .
Winston-Salem
9.4 out of 10, Exceptional, (13 reviews)
"The location was perfect for what we needed."
United States
Giuliana
$167 nightly
The price is $188
Oct 5 - Oct 6
Total with taxes and fees
La Casita .
A wooden deck with wicker furniture, a grill, and a white door.

6. Winston Sleeps 16 - 2 Kitchens Hot Tub

Winston Sleeps 16 - 2 Kitchens Hot Tub
4.0 star property
Winston-Salem
$340 nightly
The price is $384
Oct 12 - Oct 13
Total with taxes and fees
Winston Sleeps 16 - 2 Kitchens Hot Tub
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.
$252 nightly
The price is $285
Oct 4 - Oct 5
Total with taxes and fees
Log Cabin on Main St. In the ❤️ of Winston Salem. Sleeps 4 comfortably.
A modern kitchen with white cabinets, a black countertop, and a chandelier.

8. 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.
$233 nightly
The price is $263
Oct 4 - Oct 5
Total with taxes and fees
Quiet, newly renovated. Near everything!
A bedroom with a large window overlooking a forest. There is a bed with pillows and a wooden headboard.

9. The Hot Tub Hideaway

The Hot Tub Hideaway
Winston-Salem
9.6 out of 10, Exceptional, (37 reviews)
"It was a good stay"
United States
Kim R.
$236 nightly
The price is $267
Oct 4 - Oct 5
Total with taxes and fees
The Hot Tub Hideaway
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

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
$242 nightly
The price is $259
Oct 4 - Oct 5
Total with taxes and fees
Cozy 3BR Home Near Fairgrounds and Downtown
A living room with a television, leather sofas, a coffee table, a potted plant, and a chandelier.

11. 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
$199 nightly
The price is $225
Oct 11 - Oct 12
Total with taxes and fees
4 Beds | King | 85” TV | 5min to WSSU & Downtown
A compact kitchen with white cabinets, a stainless steel refrigerator, a dining table with chairs, and a small potted plant.

12. La Casita #3

La Casita #3
Winston-Salem
$8,005 nightly
The price is $9,045
Oct 5 - Oct 6
Total with taxes and fees
La Casita #3
A modern kitchen with white subway tiles, stainless steel appliances, and grey cabinetry.

13. 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.
$179 nightly
The price is $203
Oct 6 - Oct 7
Total with taxes and fees
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.

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

Cozy 2-bedroom bungalow in lovely Winston-Salem
Winston-Salem
10.0 out of 10, Exceptional, (39 reviews)
"Great place to stay we appreciate it being dog friendly"
United States
Melinda P.
$212 nightly
The price is $239
Oct 5 - Oct 6
Total with taxes and fees
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.

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

Chic 2BR/2BA Near Dining & Shops
Winston-Salem
9.6 out of 10, Exceptional, (15 reviews)
"Very clean and nice"
United States
Juancarlos
$261 nightly
The price is $279
Oct 26 - Oct 27
Total with taxes and fees
Chic 2BR/2BA Near Dining & Shops
A kitchen with wooden cabinets, a microwave, a coffee maker, and a small island with stools.

16. Quit, Cozy, Pet Friendly Condo

Quit, Cozy, Pet Friendly Condo
Winston-Salem
7.8 out of 10, Good, (8 reviews)
"It was sufficient for our short term lodging needs."
United States
Stephanie
$203 nightly
The price is $229
Oct 5 - Oct 6
Total with taxes and fees
Quit, Cozy, Pet Friendly Condo
A modern kitchen with white cabinets, stainless steel appliances, and wooden shelves.

17. Stylish 1BR Near Downtown & WFU Hospital

Stylish 1BR Near Downtown & WFU Hospital
Winston Salem
10.0 out of 10, Exceptional, (7 reviews)
"My husband stayed here for one month during an away rotation for medical school and had a wonderful experience! It’s walkable to the hospital, safe, charming, clean, stocked with all of the essentials, and the property managers are very responsive and even proactive in making the stay positive. Highly recommend!!"
United States
Anonymous traveler
$225 nightly
The price is $254
Oct 10 - Oct 11
Total with taxes and fees
Stylish 1BR Near Downtown & WFU Hospital
A bedroom with a large bed, two bedside tables, a ceiling fan, and a window with curtains.

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

Man cave, Office, Soaking tub, & Firepit.
Winston-Salem
$335 nightly
The price is $379
Oct 5 - Oct 6
Total with taxes and fees
Man cave, Office, Soaking tub, & Firepit.
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, (12 reviews)
"We loved this little cabin! Would definitely recommend!"
United States
Kathryn P.
$228 nightly
The price is $258
Oct 8 - Oct 9
Total with taxes and fees
Charming 2-bedroom cabin with WiFi in brilliant Winston-Salem
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!

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.
$257 nightly
The price is $290
Oct 4 - Oct 5
Total with taxes and fees
Cozy King Blue H2O Staycation , Stock Tank Pool, Hot Tub, Fire Pit Pets OK!
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

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

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

8/10 Good
"Need smart TV so could stream WNBA"
kathy 1-night trip
Posted 12 hours ago
Hampton Inn & Suites Winston-Salem/University Area, NC

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 $90 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.