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.
The price is CA $175
CA $362 total
includes taxes & fees
Sep 23 - Sep 24
Log Cabin on Main St. In the ❤️ of Winston Salem. Sleeps 4 comfortably.
A residential area with a bicycle parked on a concrete path, surrounded by greenery and houses.

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.
The price is CA $126
CA $210 total
includes taxes & fees
Oct 4 - Oct 5
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.
The price is CA $165
CA $335 total
includes taxes & fees
Sep 24 - Sep 25
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
The price is CA $98
CA $250 total
includes taxes & fees
Sep 27 - Sep 28
The Ardmore Executive Suite

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
The price is CA $107
CA $263 total
includes taxes & fees
Sep 23 - Sep 24
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
The price is CA $226
CA $605 total
includes taxes & fees
Sep 27 - Sep 28
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
The price is CA $170
CA $402 total
includes taxes & fees
Oct 4 - Oct 5
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.
The price is CA $210
CA $270 total
includes taxes & fees
Sep 28 - Sep 29
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, (27 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.
The price is CA $171
CA $420 total
includes taxes & fees
Sep 23 - Sep 24
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)
"I enjoyed my stay here. The property was cozy, quiet, clean, and very close to downtown. I was in the area to spend time with family, and was able to host my sister and her two kids with plenty of space. I would definitely stay here again."
United States
Bonnie F.
The price is CA $159
CA $401 total
includes taxes & fees
Sep 23 - Sep 24
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.
The price is CA $201
CA $344 total
includes taxes & fees
Sep 23 - Sep 24
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.
The price is CA $162
CA $373 total
includes taxes & fees
Sep 28 - Sep 29
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.
The price is CA $214
CA $528 total
includes taxes & fees
Sep 23 - Sep 24
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)
"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 traveller
The price is CA $92
CA $254 total
includes taxes & fees
Sep 28 - Sep 29
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.
The price is CA $189
CA $458 total
includes taxes & fees
Sep 23 - Sep 24
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
The price is CA $161
CA $406 total
includes taxes & fees
Sep 28 - Sep 29
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.
The price is CA $235
CA $409 total
includes taxes & fees
Sep 24 - Sep 25
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
The price is CA $166
CA $484 total
includes taxes & fees
Sep 23 - Sep 24
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
The price is CA $192
CA $517 total
includes taxes & fees
Sep 23 - Sep 24
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.
The price is CA $188
CA $417 total
includes taxes & fees
Sep 23 - Sep 24
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

Sleep Inn Hanes Mall

Sleep Inn Hanes Mall

8/10 Good
"I really enjoy my stay. The rooms are nice and clean and the staff are very attentive. This will be my third time staying there."
Florence 1-night trip
Posted less than an hour ago
Sleep Inn Hanes Mall

Find out more about Winston-Salem

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Winston-Salem. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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.