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 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Winston-Salem vacation rentals

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

1. 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 19 - Oct 20
Total with taxes and fees
WEST END WHISPER 3 minute walk or drive to Everything. Prime location.
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, (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.
$127 nightly
The price is $144
Oct 26 - Oct 27
Total with taxes and fees
Updated 1BR cottage on private acre+ lot
A covered porch with wooden flooring, black chairs, and hanging planters.

3. 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.
$214 nightly
The price is $242
Oct 20 - Oct 21
Total with taxes and fees
Cozy 2-bedroom bungalow in lovely Winston-Salem
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 18 - Oct 19
Total with taxes and fees
3 Mi to Dtwn Winston-Salem: Studio on Miller Park!
A modern kitchen with a wooden dining table, chairs, and a hanging light fixture.

5. 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.
$291 nightly
The price is $312
Nov 3 - Nov 4
Total with taxes and fees
Downtown Charm, 3 Bdr, Near Rest and Bars
Outdoor dining

6. La Casita .

La Casita .
Winston-Salem
9.4 out of 10, Exceptional, (14 reviews)
"The location was perfect for what we needed."
United States
Giuliana
$170 nightly
The price is $192
Oct 20 - Oct 21
Total with taxes and fees
La Casita .
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.

7. 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.
$404 nightly
The price is $457
Oct 23 - Oct 24
Total with taxes and fees
Charming 4-bedroom house in Winston-Salem near hospitals, downtown,universities
A modern kitchen with white cabinets, stainless steel appliances, and a granite countertop.

8. 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 20 - Oct 21
Total with taxes and fees
New Build Clean Modern Sleep Luxuriously 4 min from Wake Forest University
A modern kitchen with white cabinets, a black countertop, and a chandelier.

9. 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.
$234 nightly
The price is $264
Oct 19 - Oct 20
Total with taxes and fees
Quiet, newly renovated. Near everything!
A modern kitchen with white subway tiles, stainless steel appliances, and grey cabinetry.

10. 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.
$182 nightly
The price is $206
Oct 20 - Oct 21
Total with taxes and fees
La Casita #2 Great location,close to downtown Winston Salem 1 mile from UNCSA
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.

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 20 - Oct 21
Total with taxes and fees
Log Cabin on Main St. In the ❤️ of Winston Salem. Sleeps 4 comfortably.
A spacious kitchen with a granite countertop, a sink, and a dining area with a long table and chairs.

12. 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
$243 nightly
The price is $258
Nov 15 - Nov 16
Total with taxes and fees
Chic 2BR/2BA Near Dining & Shops
A modern kitchen with stainless steel appliances, white cabinetry, and a wooden dining table.

13. 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
A bedroom with a large bed, two bedside tables, a ceiling fan, and a window with curtains.

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

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

Winston Salem 3Bd 2Ba GAME ROOM mins to Downtown
Winston-Salem
9.2 out of 10, Wonderful, (22 reviews)
"Perfect place for a couple guys for one night stop on our way south for a golf trip. Quick/cheap uber ride to restaurants/town and very clean house!"
United States
Patrick R.
$290 nightly
The price is $328
Oct 21 - Oct 22
Total with taxes and fees
Winston Salem 3Bd 2Ba GAME ROOM mins to Downtown
A backyard with a fire pit, wicker furniture, a hot tub, and a hammock.

16. 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 spacious living room with a fireplace, a dining area, and a kitchen with white cabinetry.

17. Spacious 4-bedroom house with WiFi, AC in welcoming Winston-Salem, Ardmore

Spacious 4-bedroom house with WiFi, AC in welcoming Winston-Salem, Ardmore
Winston-Salem
10.0 out of 10, Exceptional, (32 reviews)
"The house is clean and spacious. The host communicates effectively. We will stay here the next time we are in the area."
United States
Hope J.
$438 nightly
The price is $495
Oct 21 - Oct 22
Total with taxes and fees
Spacious 4-bedroom house with WiFi, AC in welcoming Winston-Salem, Ardmore
A small cabin surrounded by trees with a gravel path leading to it.

18. 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 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.

19. 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
$245 nightly
The price is $262
Nov 2 - Nov 3
Total with taxes and fees
Cozy 3BR Home Near Fairgrounds and Downtown
A kitchen with white cabinets, a microwave, a sink, and a refrigerator.

20. High Ceilings | King Beds | 85” TV | Near Downtown

High Ceilings | King Beds | 85” TV | Near Downtown
Winston-Salem
7.6 out of 10, Good, (17 reviews)
"Lovely and affordable apartment with incredibly attentive and responsive host. Would totally stay again!"
United States
Caleb W.
$215 nightly
The price is $243
Oct 18 - Oct 19
Total with taxes and fees
High Ceilings | King Beds | 85” TV | Near Downtown
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

WoodSpring Suites Winston-Salem near Hanes Mall

WoodSpring Suites Winston-Salem near Hanes Mall

10/10 Excellent
"Great staff"
James 7-night trip
Posted 2 days ago
WoodSpring Suites Winston-Salem near Hanes Mall

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 $99 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.