Winston-Salem Vacation Rentals

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Vacation Rentals in Winston-Salem

In-room dining
Heated Pool King Bed Jacuzzi Bath Arcade
Heated Pool King Bed Jacuzzi Bath Arcade
4.0 star property
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
$216 nightly
The price is $244
Nov 10 - Nov 11
Total with taxes and fees
Heated Pool King Bed Jacuzzi Bath Arcade
Exterior
Charming 2-bedroom cabin with WiFi in brilliant Winston-Salem
Charming 2-bedroom cabin with WiFi in brilliant Winston-Salem
9.6 out of 10, Exceptional, (5)
"It was perfect for our needs! Ty so much for a great place to stay!"
United States
Bobby
$230 nightly
The price is $260
Nov 4 - Nov 5
Total with taxes and fees
Charming 2-bedroom cabin with WiFi in brilliant Winston-Salem
Exterior
3 mins from Downtown - PS5, King Bed & EV Charger
3 mins from Downtown - PS5, King Bed & EV Charger
2.0 star property
8.6 out of 10, Excellent, (11)
"This unit would be fine for an overnight stay but my husband and I stayed for a week and did not find it adequate. For instance, it has a comfortable bed, however, except for 3 flimsy stools in the kitchen, there are no chairs nor sofa to watch tv or read. As for the bathroom, there is a large gap all along the wall and the bathtub insert and the rusty drain is exposed. Moreover, there are no hooks to hang your used towels which becomes necessary if staying for longer than a night. Lastly,...
United States
Allan S.
$172 nightly
The price is $194
Nov 4 - Nov 5
Total with taxes and fees
3 mins from Downtown - PS5, King Bed & EV Charger
Interior
The Red Door Cabin
The Red Door Cabin
10.0 out of 10, Exceptional, (17)
"Cozy and easy place to land. If you’re looking for a spot outside of town and tucked in some woods and easy to get to, this is the spot. Super easy and comfortable."
United States
Juli M.
$238 nightly
The price is $269
Nov 4 - Nov 5
Total with taxes and fees
The Red Door Cabin
Fridge, microwave, oven, stovetop
Arcade Kid Friendly Firepit Grill HotTub
Arcade Kid Friendly Firepit Grill HotTub
3.5 star property
$386 nightly
The price is $436
Nov 4 - Nov 5
Total with taxes and fees
Arcade Kid Friendly Firepit Grill HotTub
Exterior
King Beds Hot Tub Arcade Grill & Firepit
King Beds Hot Tub Arcade Grill & Firepit
4.0 star property
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
$173 nightly
The price is $196
Nov 4 - Nov 5
Total with taxes and fees
King Beds Hot Tub Arcade Grill & Firepit
Outdoor dining
1930’s Guest Cottage and Vintage Shop with 1/2 Bath and Full Bed
1930’s Guest Cottage and Vintage Shop with 1/2 Bath and Full Bed
9.6 out of 10, Exceptional, (5)
"The cottage was super cozy; I absolutely loved it. Although our stay was short, I enjoyed it very much because of this cottage and Katy. Katy made sure we had everything we needed at all times, and she was an amazing host. I definitely would recommend this VRBO experience to anyone and everyone!"
United States
Tori B.
$95 nightly
The price is $107
Nov 30 - Dec 1
Total with taxes and fees
1930’s Guest Cottage and Vintage Shop with 1/2 Bath and Full Bed
TV, fireplace
Charming Condo Near WFU, Full Kitchen, Strong WiFi, Charming condo near WFU, full kitchen, strong Wi
Charming Condo Near WFU, Full Kitchen, Strong WiFi, Charming condo near WFU, full kitchen, strong Wi
10.0 out of 10, Exceptional, (2)
"Nice, quiet condo a short walk from WF campus and stadiums."
United States
Pete H.
$335 nightly
The price is $358
Nov 5 - Nov 6
Total with taxes and fees
Charming Condo Near WFU, Full Kitchen, Strong WiFi, Charming condo near WFU, full kitchen, strong Wi
House | Terrace/patio
Winston Sleeps 16 - 2 Kitchens Hot Tub
Winston Sleeps 16 - 2 Kitchens Hot Tub
3.5 star property
$359 nightly
The price is $406
Nov 4 - Nov 5
Total with taxes and fees
Winston Sleeps 16 - 2 Kitchens Hot Tub
Exterior
The Ardmore Executive Suite
The Ardmore Executive Suite
3.5 star property
6.0 out of 10, (3)
"Starts off the pictures are lies. I booked thinking I was getting a great place. They put me in the basement. Entrance was broken. Entry was nasty. The place had crumbs and hair. The huge TV didn’t work. Pillowcase didn’t fit the pillow. Bugs crawling including roaches. Child safety locks on everything. Holes in walls. Prey you don’t stay there and others are upstairs you will hear every footstep and conversation. Grill was rusted and nasty. Hot tub be prepared to pay extra as well...
United States
Anonymous traveler
$151 nightly
The price is $170
Nov 4 - Nov 5
Total with taxes and fees
The Ardmore Executive Suite
Fridge, microwave, coffee/tea maker, cookware/dishes/utensils
The Hot Tub Hideaway
The Hot Tub Hideaway
9.6 out of 10, Exceptional, (25)
"Very cozy and nice area. Off the beaten path. "
United States
Vicki O.
$238 nightly
The price is $269
Nov 4 - Nov 5
Total with taxes and fees
The Hot Tub Hideaway
Interior
Winston Salem 3Bd 2Ba GAME ROOM mins to Downtown
Winston Salem 3Bd 2Ba GAME ROOM mins to Downtown
9.6 out of 10, Exceptional, (8)
"Nice location "
United States
Benelli T.
$307 nightly
The price is $347
Nov 4 - Nov 5
Total with taxes and fees
Winston Salem 3Bd 2Ba GAME ROOM mins to Downtown
Interior
Hartman Casita! Quiet neighborhood.1 king Bed!
Hartman Casita! Quiet neighborhood.1 king Bed!
9.8 out of 10, Exceptional, (20)
"Beautiful house with everything you need with great proximity to Winston Salem. Host is friendly and very prompt with communication"
United States
Kevin D.
$345 nightly
The price is $369
Nov 5 - Nov 6
Total with taxes and fees
Hartman Casita! Quiet neighborhood.1 king Bed!
Outdoor dining
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.
9.6 out of 10, Exceptional, (15)
"Proximity to campus "
United States
Marcia K.
$212 nightly
The price is $239
Nov 4 - Nov 5
Total with taxes and fees
Log Cabin on Main St. In the ❤️ of Winston Salem. Sleeps 4 comfortably.
Exterior
Cozy Winston-Salem Vacation Cabin
Cozy Winston-Salem Vacation Cabin
2.0 star property
8.0 out of 10, Very Good, (4)
"We rented the property for our O40 soccer team for a tourney in Winston. It had plenty of room for the crew with lots of beds. The location was good with a nice wooded backyard. The house was fine, but could use some updating and probably a bit more seating options in the living room and king suite upstairs. Also, sponges or scrubbies in the kitchen would have been nice. All in all, though, it served the purpose and was a great house for our needs. Juan was really responsive and a great host."
United States
Brett T.
$410 nightly
The price is $463
Nov 4 - Nov 5
Total with taxes and fees
Cozy Winston-Salem Vacation Cabin
Private kitchen
Spacious 3-Bedroom with 4 beds, Fully Furnished Home Near Downtown Winston-Salem
Spacious 3-Bedroom with 4 beds, Fully Furnished Home Near Downtown Winston-Salem
10.0 out of 10, Exceptional, (2)
"We enjoyed our short stay, house is very cute and cozy and well put together "
United States
Anonymous traveler
$218 nightly
The price is $247
Nov 9 - Nov 10
Total with taxes and fees
Spacious 3-Bedroom with 4 beds, Fully Furnished Home Near Downtown Winston-Salem
Terrace/patio
Cozy 2-bedroom bungalow in lovely Winston-Salem
Cozy 2-bedroom bungalow in lovely Winston-Salem
10.0 out of 10, Exceptional, (10)
"Stayed a week while we dropped off our daughter for a summer program at Wake Forest. The house was well lit from the outside which made it easy to use the simple comb door lock as we arrived after dark. The house is spacious, has very comfortable seating in the living room nice dining table and great kitchen. So many amenities from snacks, teas and coffees and sugar and cream, to soaps, make up remover, toothbrushes and toothpastes lotion and even face scrub and face masks, plenty of toilet...
United States
Rebecca M.
$230 nightly
The price is $260
Nov 15 - Nov 16
Total with taxes and fees
Cozy 2-bedroom bungalow in lovely Winston-Salem
Dining
Rosewood Loft I Upper Suite
Rosewood Loft I Upper Suite
10.0 out of 10, Exceptional, (1)
"The host was very easy to contact. The space was clean and it was very easy to find things that we needed. We really appreciated the necessities towel bundle. The space felt welcoming and comfortable."
United States
Delores C.
$311 nightly
The price is $351
Nov 4 - Nov 5
Total with taxes and fees
Rosewood Loft I Upper Suite
Exterior
The Sunrise! Close to Wake forest University. 2 King beds. Quiet neighborhood!
The Sunrise! Close to Wake forest University. 2 King beds. Quiet neighborhood!
9.6 out of 10, Exceptional, (30)
"Super clean, cute, and location was perfect!"
United States
Sydney S.
$360 nightly
The price is $407
Nov 4 - Nov 5
Total with taxes and fees
The Sunrise! Close to Wake forest University. 2 King beds. Quiet neighborhood!
Exterior
Updated 1BR cottage on private acre+ lot
Updated 1BR cottage on private acre+ lot
10.0 out of 10, Exceptional, (13)
"I will love to recommend this home away from home. It’s very close to everything and a very peaceful stay. "
United States
Nina J.
$122 nightly
The price is $138
Nov 12 - Nov 13
Total with taxes and fees
Updated 1BR cottage on private acre+ lot
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
"nice room"
Douglas 2-night trip
Posted 3 days 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 $170 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 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?

Charming 4-bedroom house with AC and WiFi in wonderful Winston-Salem: This Winston-Salem vacation home rental has air-conditioning and laundry facilities 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. Another good choice for your trip to Winston-Salem is 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 191 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.