Winston-Salem Vacation Rentals

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Oct 10 - Oct 12
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Oct 24 - Oct 26
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Dec 19 - Dec 21

Vacation Rentals in Winston-Salem

Our top choices for Winston-Salem vacation rentals

Landing Winston-Salem near Wake Forest University
Interior

Landing Winston-Salem near Wake Forest University

4.0 star property
7.4 out of 10, Good, (3)
Landing Winston-Salem near Wake Forest University
The Hot Tub Hideaway
Fridge, microwave, coffee/tea maker, cookware/dishes/utensils

The Hot Tub Hideaway

9.6 out of 10, Exceptional, (24)
"Stay is awesome!"
The price is ￥23,470
￥39,698 total
includes taxes & fees
Sep 30 - Oct 1
The Hot Tub Hideaway
Cozy 2-bedroom bungalow in lovely Winston-Salem
Terrace/patio

Cozy 2-bedroom bungalow in lovely Winston-Salem

10.0 out of 10, Exceptional, (8)
"We enjoyed our stay and loved the house. Great location for our needs."
The price is ￥19,337
￥38,197 total
includes taxes & fees
Oct 1 - Oct 2
Cozy 2-bedroom bungalow in lovely Winston-Salem
Cozy King Blue H2O Staycation , Stock Tank Pool, Hot Tub, Fire Pit Pets OK!
Fridge, microwave, oven, stovetop

Cozy King Blue H2O Staycation , Stock Tank Pool, Hot Tub, Fire Pit Pets OK!

10.0 out of 10, Exceptional, (47)
"Lovely space... super clean and cozy, close to everything in Winston-Salem but secluded enough. We will be definitely staying here again when we come back next year."
The price is ￥18,599
￥34,697 total
includes taxes & fees
Oct 8 - Oct 9
Cozy King Blue H2O Staycation , Stock Tank Pool, Hot Tub, Fire Pit Pets OK!
WEST END WHISPER 3 minute walk or drive to Everything. Prime location.
Property grounds

WEST END WHISPER 3 minute walk or drive to Everything. Prime location.

10.0 out of 10, Exceptional, (2)
"Fantastic location, super clean and convenient to all Winston-Salem attractions, walking distance for most, including Reynolda and WFU. Host is available and guests can park in front of the unit. "
WEST END WHISPER 3 minute walk or drive to Everything. Prime location.
King Beds Hot Tub Arcade Grill & Firepit
Exterior

King Beds Hot Tub Arcade Grill & Firepit

4.0 star property
The price is ￥32,315
￥42,974 total
includes taxes & fees
Oct 1 - Oct 2
King Beds Hot Tub Arcade Grill & Firepit
Charming & Modern Home / Prime Location / Sleeps 8
Fridge, microwave, oven, stovetop

Charming & Modern Home / Prime Location / Sleeps 8

9.4 out of 10, Exceptional, (9)
"Great stay and the property was pictured exactly how it was. Perfect for our family as we visited our oldest who is living in Winston-Salem."
Charming & Modern Home / Prime Location / Sleeps 8
The Ardmore Executive Suite
Exterior

The Ardmore Executive Suite

3.5 star property
6.0 out of 10, (3)
"Very clean and nice setup "
The price is ￥22,448
￥36,437 total
includes taxes & fees
Oct 8 - Oct 9
The Ardmore Executive Suite
The Ardmore Executive Suite
Outdoor spa tub

The Ardmore Executive Suite

8.0 out of 10, Very Good, (1)
"Overall, my stay was nice and was a great location for my daughter, granddaughters, and myself to celebrate my granddaughter's birthday, shop, eat dinner, and spend time together. The living space was nice, bed in the bedroom was comfortable, the pull out beds from two couches were not as comfortable, but my granddaughters enjoyed the board games that were there. The place was well furnished and clean. The upstair guests were doing karaoke which was somewhat loud late night. The most...
The price is ￥24,356
￥45,141 total
includes taxes & fees
Sep 29 - Sep 30
The Ardmore Executive Suite
High ceiling house close to downtown
3 bedrooms, free WiFi

High ceiling house close to downtown

7.8 out of 10, Good, (9)
"Nicely upgraded older home. It’s clean and very comfortable. The beds are comfy and big tv in each room. Huge back yard. Quiet neighborhood."
The price is ￥10,495
￥25,204 total
includes taxes & fees
Sep 25 - Sep 26
High ceiling house close to downtown
La Casita: A Cozy Retreat Near Wake Forest University"
Exterior detail

La Casita: A Cozy Retreat Near Wake Forest University"

9.6 out of 10, Exceptional, (50)
"Adorable house with all the amenities. Excellent location when visiting Wake Forest. "
The price is ￥17,176
￥40,926 total
includes taxes & fees
Oct 8 - Oct 9
La Casita: A Cozy Retreat Near Wake Forest University"
Charming 2-bedroom cabin with WiFi in brilliant Winston-Salem
Exterior

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!"
The price is ￥21,123
￥38,215 total
includes taxes & fees
Oct 8 - Oct 9
Charming 2-bedroom cabin with WiFi in brilliant Winston-Salem
Charming 4-bedroom house with AC and WiFi in wonderful Winston-Salem
Fridge, microwave, oven, stovetop

Charming 4-bedroom house with AC and WiFi in wonderful Winston-Salem

9.0 out of 10, Wonderful, (2)
"Overall pleasant stay"
The price is ￥27,898
￥101,914 total
includes taxes & fees
Sep 30 - Oct 1
Charming 4-bedroom house with AC and WiFi in wonderful Winston-Salem
Log Cabin on Main St. In the ❤️ of Winston Salem. Sleeps 4 comfortably.
Outdoor dining

Log Cabin on Main St. In the ❤️ of Winston Salem. Sleeps 4 comfortably.

9.6 out of 10, Exceptional, (15)
"Wonderful stay! "
The price is ￥16,606
￥34,947 total
includes taxes & fees
Oct 8 - Oct 9
Log Cabin on Main St. In the ❤️ of Winston Salem. Sleeps 4 comfortably.
Arcade Kid Friendly Firepit Grill HotTub
Fridge, microwave, oven, stovetop

Arcade Kid Friendly Firepit Grill HotTub

3.5 star property
The price is ￥48,274
￥91,477 total
includes taxes & fees
Oct 6 - Oct 7
Arcade Kid Friendly Firepit Grill HotTub
InTown Suites Extended Stay Greensboro NC - Airport
Free WiFi, bed sheets

InTown Suites Extended Stay Greensboro NC - Airport

2.0 star property
6.2 out of 10, (665)
"Front desk was handled very beautifully."
InTown Suites Extended Stay Greensboro NC - Airport
Newly Renovated 3BR, 2BA, pet friendly, with 3 kayaks, boat ramp nearby
Exterior

Newly Renovated 3BR, 2BA, pet friendly, with 3 kayaks, boat ramp nearby

10.0 out of 10, Exceptional, (186)
"There was everything that you would ever need in this cute remodeled home. Everything was nice and clean and we had a wonderful stay. I would love to come back to visit again."
Newly Renovated 3BR, 2BA, pet friendly, with 3 kayaks, boat ramp nearby
⭐️ Amelia’s Retreat ⭐️ @ Greensboro 🐕🏥🏙🏊‍♀️🛍🍔🥂 Close
Terrace/patio

⭐️ Amelia’s Retreat ⭐️ @ Greensboro 🐕🏥🏙🏊‍♀️🛍🍔🥂 Close

9.8 out of 10, Exceptional, (61)
"Home was clean, great location. "
The price is ￥24,963
￥46,465 total
includes taxes & fees
Oct 9 - Oct 10
⭐️ Amelia’s Retreat ⭐️ @ Greensboro 🐕🏥🏙🏊‍♀️🛍🍔🥂 Close
Lakefront/Boat Dock, 3/2, Furnished, Castaway Cottage, covered back deck views
Outdoor dining

Lakefront/Boat Dock, 3/2, Furnished, Castaway Cottage, covered back deck views

9.8 out of 10, Exceptional, (149)
"The house was really nice and the back porch was awesome boat dock was really nice"
Lakefront/Boat Dock, 3/2, Furnished, Castaway Cottage, covered back deck views
Charming 2-bedroom Cottage with AC and WiFi in Pilot Mountain
Exterior

Charming 2-bedroom Cottage with AC and WiFi in Pilot Mountain

8.8 out of 10, Excellent, (17)
"We had a great stay for a quick trip to see family! "
The price is ￥12,621
￥30,941 total
includes taxes & fees
Sep 28 - Sep 29
Charming 2-bedroom Cottage with AC and WiFi in Pilot Mountain
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

Hawthorne Inn and Conference Center

Hawthorne Inn and Conference Center

10/10 Excellent
"This hotel is terrific! I am so glad I stayed there. People were great! Room was great! View of trees from my big glass windows was great! I will recommend Hawthorne Inn and Conference Center and stay there again myself."
sue 2-night trip
Posted 3 days ago
Hawthorne Inn and Conference Center

Find out more about Winston-Salem

Find out more about Winston-Salem

Search for holiday rentals in Winston-Salem on Expedia! You can easily find your home rentals, villas, holiday apartments in Winston-Salem using one of the methods below:

  • View our selection of featured holiday rentals in Winston-Salem
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  • Enter your travel dates to view the best deals on holiday rentals in Winston-Salem while they last

Look no further and take a look at our great range of rental properties in Winston-Salem!

Explore a world of travel with Expedia

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?

Cozy King Blue H2O Staycation , Stock Tank Pool, Hot Tub, Fire Pit Pets OK!: This highly rated vacation home rental in Winston-Salem is located in the city center and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. You can relax into your vacation with a selection of games and a hot tub.

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

Choose from 188 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.