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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 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.
$184 nightly
The price is $208
Oct 26 - Oct 27
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.
$117 nightly
The price is $132
Oct 26 - Oct 27
Total with taxes and fees
Updated 1BR cottage on private acre+ lot
A rustic wooden cabin with a porch, surrounded by greenery and a tree with pink flowers.

3. 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 26 - Oct 27
Total with taxes and fees
Log Cabin on Main St. In the ❤️ of Winston Salem. Sleeps 4 comfortably.
Outdoor dining

4. La Casita .

La Casita .
Winston-Salem
9.4 out of 10, Exceptional, (16 reviews)
"The location was perfect for what we needed."
United States
Giuliana
$167 nightly
The price is $189
Oct 26 - Oct 27
Total with taxes and fees
La Casita .
A covered porch with wooden flooring, black chairs, and hanging planters.

5. 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 26 - Oct 27
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.

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
$250 nightly
The price is $266
Oct 26 - Oct 27
Total with taxes and fees
Chic 2BR/2BA Near Dining & Shops
A modern kitchen with white subway tiles, stainless steel appliances, and grey cabinetry.

7. 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 26 - Oct 27
Total with taxes and fees
La Casita #2 Great location,close to downtown Winston Salem 1 mile from UNCSA
A bedroom with a large window overlooking a forest. There is a bed with pillows and a wooden headboard.

8. 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.
$220 nightly
The price is $249
Oct 26 - Oct 27
Total with taxes and fees
The Hot Tub Hideaway
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 26 - Oct 27
Total with taxes and fees
Quiet, newly renovated. Near everything!
A yellow house with a red door, a brick chimney, and a front yard with small bushes.

10. 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
Nov 1 - Nov 2
Total with taxes and fees
3 Mi to Dtwn Winston-Salem: Studio on Miller Park!
A backyard with a fire pit, wicker furniture, a hot tub, and a hammock.

11. 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
Nov 1 - Nov 2
Total with taxes and fees
Cozy King Blue H2O Staycation , Stock Tank Pool, Hot Tub, Fire Pit Pets OK!
A small cabin surrounded by trees with a gravel path leading to it.

12. The Red Door Cabin

The Red Door Cabin
Winston-Salem
10.0 out of 10, Exceptional, (28 reviews)
"Cute place. "
United States
Sue C.
$220 nightly
The price is $249
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.

13. 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 spacious living room with a brown leather sectional sofa, a coffee table with books, and a dining area in the background.

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

Man cave, Office, Soaking tub, & Firepit.
Winston-Salem
$339 nightly
The price is $383
Oct 26 - Oct 27
Total with taxes and fees
Man cave, Office, Soaking tub, & Firepit.
A covered porch with two wicker chairs and a small table, a brick wall, and a view of a street and trees.

15. 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
9.0 out of 10, Wonderful, (4 reviews)
"The location of this property is in a nice residential part of town and the house itself is charming. We were able to come and go with ease. Wifi connectivity was super quick and easy and having two full bathrooms was nice."
United States
Lindsey G.
$265 nightly
The price is $300
Oct 26 - Oct 27
Total with taxes and fees
Recently renovated luxury duplex unit. Short walk to Atrium WF Baptist Hospital!
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.
$284 nightly
The price is $305
Nov 3 - Nov 4
Total with taxes and fees
Downtown Charm, 3 Bdr, Near Rest and Bars
A modern kitchen with wooden cabinets, a built-in microwave, and a large island.

17. 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, (13 reviews)
"We loved this little cabin! Would definitely recommend!"
United States
Kathryn P.
$230 nightly
The price is $260
Oct 26 - Oct 27
Total with taxes and fees
Charming 2-bedroom cabin with WiFi in brilliant Winston-Salem
A modern kitchen with white cabinets, stainless steel appliances, and a granite countertop.

18. 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 26 - Oct 27
Total with taxes and fees
New Build Clean Modern Sleep Luxuriously 4 min from Wake Forest University
A kitchen with white cabinets, a granite countertop, and a black stove.

19. Cute cottage in a rural setting

Cute cottage in a rural setting
Clemmons
7.4 out of 10, Good, (11 reviews)
"It was really nice especially communication and help from the host who helped us with some lost items after we left"
United States
Seli J.
$269 nightly
The price is $288
Oct 26 - Oct 27
Total with taxes and fees
Cute cottage in a rural setting
A modern kitchen with a large island, bar stools, and pendant lighting.

20. 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, (62 reviews)
"This is a great place. Clean, updated, close to wake Forest U and the host was perfect - highly recommend."
United States
Melissa T.
$247 nightly
The price is $279
Oct 26 - Oct 27
Total with taxes and fees
La Casita: A Cozy Retreat Near Wake Forest University"
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

La Quinta Inn & Suites by Wyndham Winston-Salem

La Quinta Inn & Suites by Wyndham Winston-Salem

10/10 Excellent
"This is the second time that I have stayed at this hotel. Both times have been spot on. Everyone is very friendly and courteous! The front desk staff is amazing! They speak every time they see you, they ask if everything is going well and want to know if you need anything! Room is clean and breakfast is fresh and good. Thanks for a wonderful stay!"
Debbie 4-night trip
Posted 14 hours ago
La Quinta Inn & Suites by Wyndham Winston-Salem

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 $132 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.

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