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 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Winston-Salem vacation rentals

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

1. 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.
$226 nightly
The price is $255
Sep 27 - Sep 28
Total with taxes and fees
Log Cabin on Main St. In the ❤️ of Winston Salem. Sleeps 4 comfortably.
A living room with a sofa, a chair, a coffee table, a lamp, and a framed picture on the wall.

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
9.4 out of 10, Exceptional, (32 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.
$123 nightly
The price is $139
Sep 30 - Oct 1
Total with taxes and fees
WEST END WHISPER 3 minute walk or drive to Everything. Prime location.
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, (38 reviews)
"Great place to stay we appreciate it being dog friendly"
United States
Melinda P.
$212 nightly
The price is $239
Sep 28 - Sep 29
Total with taxes and fees
Cozy 2-bedroom bungalow in lovely Winston-Salem
A modern kitchen with white cabinets, stainless steel appliances, and a marble countertop.

4. 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
$175 nightly
The price is $198
Sep 29 - Sep 30
Total with taxes and fees
The Ardmore Executive Suite

5. La Casita .

La Casita .
Winston-Salem
9.4 out of 10, Exceptional, (13 reviews)
$167 nightly
The price is $188
Sep 28 - Sep 29
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
$420 nightly
The price is $475
Sep 29 - Sep 30
Total with taxes and fees
Winston Sleeps 16 - 2 Kitchens Hot Tub
A modern kitchen with white cabinets, a stainless steel refrigerator, and a tiled backsplash.

7. King Beds Hot Tub Arcade Grill & Firepit

King Beds Hot Tub Arcade Grill & Firepit
4.5 star property
Winston-Salem
8.6 out of 10, Excellent, (4 reviews)
"Loved this little house and all the attention to detail! Would definitely return."
United States
Brittney N
$283 nightly
The price is $320
Oct 4 - Oct 5
Total with taxes and fees
King Beds Hot Tub Arcade Grill & Firepit
A kitchen with a white bar counter, wooden cabinets, a coffee maker, and a decorative plate on the wall.

8. Cozy 1-bedroom condo in Downtown Winston-Salem, free parking!

Cozy 1-bedroom condo in Downtown Winston-Salem, free parking!
Winston-Salem
9.0 out of 10, Wonderful, (13 reviews)
"Great location and very communicative host!"
United States
Claudia M.
$172 nightly
The price is $194
Sep 27 - Sep 28
Total with taxes and fees
Cozy 1-bedroom condo in Downtown Winston-Salem, free parking!
A modern kitchen with a wooden dining table, chairs, and a hanging light fixture.

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

Downtown Charm, 3 Bdr, Near Rest and Bars
Winston-Salem
9.4 out of 10, Exceptional, (28 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.
$279 nightly
The price is $299
Sep 29 - Sep 30
Total with taxes and fees
Downtown Charm, 3 Bdr, Near Rest and Bars
A modern kitchen with a large island, bar stools, and pendant lighting.

10. La Casita: A Cozy Retreat Near Wake Forest University"

La Casita: A Cozy Retreat Near Wake Forest University"
Winston-Salem
9.6 out of 10, Exceptional, (60 reviews)
$257 nightly
The price is $290
Sep 29 - Sep 30
Total with taxes and fees
La Casita: A Cozy Retreat Near Wake Forest University"
A bedroom with a large window overlooking a forest. There is a bed with pillows and a wooden headboard.

11. 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
Sep 27 - Sep 28
Total with taxes and fees
The Hot Tub Hideaway
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, (33 reviews)
"In town for work. Was a Great stay. Staying there again this week"
United States
Natalie K.
$226 nightly
The price is $255
Sep 28 - Sep 29
Total with taxes and fees
Quiet, newly renovated. Near everything!
A modern kitchen with white cabinets, stainless steel appliances, and a granite countertop.

13. 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.
$331 nightly
The price is $374
Sep 27 - Sep 28
Total with taxes and fees
New Build Clean Modern Sleep Luxuriously 4 min from Wake Forest University
A yellow house with a red door, a brick chimney, and a front yard with small bushes.

14. 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)
"Nice studio close to Miller Park. Host very easy to communicate with. My husband and I enjoyed the stay. Close to restaurants and stores as well. Would happily stay again."
United States
Catherine D.
$161 nightly
The price is $182
Sep 28 - Sep 29
Total with taxes and fees
3 Mi to Dtwn Winston-Salem: Studio on Miller Park!
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
9.4 out of 10, Exceptional, (20 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.
$288 nightly
The price is $325
Sep 27 - Sep 28
Total with taxes and fees
Winston Salem 3Bd 2Ba GAME ROOM mins to Downtown
A modern kitchen with stainless steel appliances, white cabinetry, and a wooden dining table.

16. 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
9.4 out of 10, Exceptional, (13 reviews)
"Host was very friendly - place was super clean and exactly as listed!"
United States
Brittany
$254 nightly
The price is $287
Oct 5 - Oct 6
Total with taxes and fees
Charming 2-bed, 2 full bath lower level studio with WiFi, AC in Ardmore
A backyard with a fire pit, wicker furniture, a hot tub, and a hammock.

17. 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.
$248 nightly
The price is $280
Sep 27 - Sep 28
Total with taxes and fees
Cozy King Blue H2O Staycation , Stock Tank Pool, Hot Tub, Fire Pit Pets OK!
A room with a dark wall, a brown leather sofa, a round coffee table, and a large window with curtains.

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

Man cave, Office, Soaking tub, & Firepit.
Winston-Salem
$312 nightly
The price is $353
Sep 28 - Sep 29
Total with taxes and fees
Man cave, Office, Soaking tub, & Firepit.
A spacious living room with a large sectional sofa, a green chair, and a coffee table. A staircase with white railings is visible in the background.

19. Spacious Historical Home 3 mins from Downtown

Spacious Historical Home 3 mins from Downtown
Winston-Salem
8.8 out of 10, Excellent, (3 reviews)
"I recommend this 👌"
United States
Melvin
$325 nightly
The price is $367
Sep 29 - Sep 30
Total with taxes and fees
Spacious Historical Home 3 mins from Downtown
A covered porch with two wicker chairs and a small table, a brick wall, and a view of a street and trees.

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

Recently renovated luxury duplex unit. Short walk to Atrium WF Baptist Hospital!
Winston-Salem
8.0 out of 10, Very good, (2 reviews)
"Overall had good amenities and was nicely renovated and decorated. Disappointed in the initial cleanliness of the unit for the price paid"
United States
Tatiana U.
$263 nightly
The price is $297
Sep 27 - Sep 28
Total with taxes and fees
Recently renovated luxury duplex unit. Short walk to Atrium WF Baptist Hospital!
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

10/10 Excellent
"Quick trip, ladies at front desk were super nice"
Justin 1-night trip
Posted 17 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 Cozy King Blue H2O Staycation , Stock Tank Pool, Hot Tub, Fire Pit Pets OK!.

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.