Winston-Salem Vacation Rentals

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Our top choices for Winston-Salem vacation rentals

The Hot Tub Hideaway

The Hot Tub Hideaway
Winston-Salem
9.6 out of 10, Exceptional, (32 reviews)
"It was a good stay"
United States
Kim R.
The Hot Tub Hideaway

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, (8 reviews)
"It was perfect for our needs! Ty so much for a great place to stay!"
United States
Bobby
Charming 2-bedroom cabin with WiFi in brilliant Winston-Salem

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, (11 reviews)
"Host was fantastic!! Couldn't have asked for a better experience. Everything I needed was readily accessible. Looking forward to my next stay!!"
United States
mike j.
Charming 2-bed, 2 full bath lower level studio with WiFi, AC in Ardmore

La Casita .

La Casita .
Winston-Salem
10.0 out of 10, Exceptional, (3 reviews)
"Overall a great place to stay. Super cozy! "
United States
Darren L.
La Casita .

The Red Door Cabin

The Red Door Cabin
Winston-Salem
10.0 out of 10, Exceptional, (23 reviews)
"Very clean and secluded but still close to the city. Thank you"
United States
Michael S.
The Red Door Cabin

Quiet, newly renovated. Near everything!

Quiet, newly renovated. Near everything!
Winston-Salem
10.0 out of 10, Exceptional, (27 reviews)
"The property was clean, and comfortable in a nice neighborhood close to amenities."
United States
Maria H.
Quiet, newly renovated. Near everything!

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, (54 reviews)
"Very nice place to stay! "
United States
Kirby M.
La Casita: A Cozy Retreat Near Wake Forest University"

La Casita #3

La Casita #3
Winston-Salem
La Casita #3

2-bedroom cottage perfect for Furniture Market

2-bedroom cottage perfect for Furniture Market
Winston-Salem
9.0 out of 10, Wonderful, (2 reviews)
"Nice stay. Would recommend for your visit to the area."
United States
Charles G.
2-bedroom cottage perfect for Furniture Market

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
La Casita #2 Great location,close to downtown Winston Salem 1 mile from UNCSA

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
9.8 out of 10, Exceptional, (51 reviews)
"We had a very relaxing stay here. The hot tub was lovely and the property was very close to a lot of shopping/restaurants. "
United States
Taylor E.
Cozy King Blue H2O Staycation , Stock Tank Pool, Hot Tub, Fire Pit Pets OK!

Cozy 3BR Home Near Fairgrounds and Downtown

Cozy 3BR Home Near Fairgrounds and Downtown
Winston-Salem
Cozy 3BR Home Near Fairgrounds and Downtown

Luxury 3BR Townhome - Sleep 6

Luxury 3BR Townhome - Sleep 6
Winston-Salem
9.2 out of 10, Wonderful, (49 reviews)
"The amenities were great as was the location for us."
United States
jeanne k.
Luxury 3BR Townhome - Sleep 6

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

Urban Escape 3 Bed 2.5 Bath Near Wake Forest

Urban Escape 3 Bed 2.5 Bath Near Wake Forest
Winston-Salem
9.4 out of 10, Exceptional, (13 reviews)
"They have were very welcoming. We thoroughly enjoyed our stay there while moving our daughter, son-in-law and new grandbaby into their new home. It felt like you were out in the country, but yet you were right there where everything was. Perfect location."
United States
Jill H.
Urban Escape 3 Bed 2.5 Bath Near Wake Forest

Arcade Kid Friendly Firepit Grill HotTub

Arcade Kid Friendly Firepit Grill HotTub
4.0 star property
Winston-Salem
Arcade Kid Friendly Firepit Grill HotTub

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
4 Beds | King | 85” TV | 5min to WSSU & Downtown

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
9.6 out of 10, Exceptional, (19 reviews)
"Wonderful stay! "
United States
Hannah J.
Log Cabin on Main St. In the ❤️ of Winston Salem. Sleeps 4 comfortably.

Modern 2BR Retreat | 85” TV Ultra-Comfy king Beds

Modern 2BR Retreat | 85” TV Ultra-Comfy king Beds
Winston-Salem
9.0 out of 10, Wonderful, (2 reviews)
"Very clean. Fairly quiet neighborhood. Huge TV’s. Great relaxing after a days work. Kitchen could benefit from a dish drain rack. Would happily stay there again. "
United States
John
Modern 2BR Retreat | 85” TV Ultra-Comfy king Beds

Cozy Cottage: Nature-filled Winston-salem Retreat!

Cozy Cottage: Nature-filled Winston-salem Retreat!
3.0 star property
Winston-Salem
Cozy Cottage: Nature-filled Winston-salem Retreat!
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

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 $130 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.

Frequently asked questions

Can I find vacation rentals in Winston-Salem?

Yes, there are vacation rentals in Winston-Salem close to Airbound Trampoline Park, 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?

Quiet, newly renovated. Near everything!: This highly rated vacation home rental in Winston-Salem offers a fireplace, a selection of games, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

How many vacation rentals will I find in Winston-Salem?

Choose from 216 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 Southeastern Center for Contemporary 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.