Photo by David Bjorgen

Winston-Salem Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out
  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals
  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings
  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

This weekend
Next weekend

Our top choices for Winston-Salem vacation rentals

King Beds Hot Tub Arcade Grill & Firepit

King Beds Hot Tub Arcade Grill & Firepit
4.0 star property
Winston-Salem
8.0 out of 10, Very Good, (1)
"House was clean and amenities were good. House is in a great location. Be aware that there is another rental unit downstairs that may have other parties occuppying."
United States
Elizabeth
King Beds Hot Tub Arcade Grill & Firepit

Heated Pool King Bed Jacuzzi Bath Arcade

Heated Pool King Bed Jacuzzi Bath Arcade
4.0 star property
Winston-Salem
8.0 out of 10, Very Good, (1)
"The house was very clean, comfortable, and nicely maintained, which we really appreciated during our stay. However, there were two downsides to be aware of. First, after booking, the owner asked us to pay an extra money for cleaning fee, even though it was not clearly listed in the Expedia booking details. I chose not to argue since I didn’t want to ruin our family trip, but future guests should expect additional charges. Second, privacy was an issue the owner lives in the basement, and it felt...
United States
Rami
$284 nightly
The price is $321
Jan 11 - Jan 12, 2026
Total with taxes and fees
Heated Pool King Bed Jacuzzi Bath Arcade

Cozy Cottage: Nature-filled Winston-salem Retreat!

Cozy Cottage: Nature-filled Winston-salem Retreat!
3.0 star property
Winston-Salem
$425 nightly
The price is $455
Dec 30 - Dec 31
Total with taxes and fees
Cozy Cottage: Nature-filled Winston-salem Retreat!

Arcade Kid Friendly Firepit Grill HotTub

Arcade Kid Friendly Firepit Grill HotTub
3.5 star property
Winston-Salem
$395 nightly
The price is $447
Jan 5 - Jan 6, 2026
Total with taxes and fees
Arcade Kid Friendly Firepit Grill HotTub

Winston Sleeps 16 - 2 Kitchens Hot Tub

Winston Sleeps 16 - 2 Kitchens Hot Tub
3.5 star property
Winston-Salem
Winston Sleeps 16 - 2 Kitchens Hot Tub

The Ardmore Executive Suite

The Ardmore Executive Suite
3.5 star property
Winston-Salem
6.0 out of 10, (3)
"Very clean and nice setup "
United States
Nicholas
The Ardmore Executive Suite

Bright & Elegant Home in High Point w/ Deck!

Bright & Elegant Home in High Point w/ Deck!
3.0 star property
High Point
$394 nightly
The price is $422
Jan 4 - Jan 5, 2026
Total with taxes and fees
Bright & Elegant Home in High Point w/ Deck!

KingBed Hot Tub BBQ Games Hypoallergenic

KingBed Hot Tub BBQ Games Hypoallergenic
3.5 star property
Kernersville
4.8 out of 10, (3)
"We ended up not staying because after i booked they listed all the fees. You have to check in by 8 pm but is listed as 2:30am and there is a $20 per person per day fee to use the pool. And you have to give a 48 hr notice to even use the pool and i booked last minute so that would have been a waste too. To use the hot tub its $100 extra but that is the only thing listed before you book. It would not have been worth the 3.5 hr drive we were going to make. "
United States
Tiffany
$194 nightly
The price is $219
Dec 30 - Dec 31
Total with taxes and fees
KingBed Hot Tub BBQ Games Hypoallergenic

Kernersville Hot Tub Pool Arcade Gym Wifi Coffee

Kernersville Hot Tub Pool Arcade Gym Wifi Coffee
3.0 star property
Kernersville
6.0 out of 10, (4)
"The house was very nice. Very well kept up. Enjoyed the atmosphere. Hope to stay there again. Great experience. 😃"
United States
Troy
$421 nightly
The price is $476
Jan 11 - Jan 12, 2026
Total with taxes and fees
Kernersville Hot Tub Pool Arcade Gym Wifi Coffee

Exec Suite King Bed Hot Tub Gym Laundry

Exec Suite King Bed Hot Tub Gym Laundry
4.0 star property
Kernersville
$260 nightly
The price is $294
Jan 7 - Jan 8, 2026
Total with taxes and fees
Exec Suite King Bed Hot Tub Gym Laundry
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.
Save an average of 15% on thousands of hotels when you're signed in

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 $102 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?

The Sunrise! Close to Wake forest University. 2 King beds. Quiet neighborhood!: This Winston-Salem vacation home rental offers a fireplace, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games. Another good choice for your trip to Winston-Salem is La Casita: A Cozy Retreat Near Wake Forest University".

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

Choose from 215 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.