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
17 Jul - 19 Jul
In two months
28 Aug - 30 Aug
In three months
25 Sep - 27 Sep
In four months
23 Oct - 25 Oct

Our top choices for Winston-Salem vacation rentals

House | Private kitchen | Fridge, microwave, oven, stovetop

King Beds Hot Tub Arcade Grill & Firepit

King Beds Hot Tub Arcade Grill & Firepit
4.5 star property
Winston-Salem
9.4 out of 10, Exceptional, (3 reviews)
"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
The price is SAR 524
SAR 1,155 total
includes taxes & fees
5 Jul - 6 Jul
King Beds Hot Tub Arcade Grill & Firepit
House | Terrace/patio

Winston Sleeps 16 - 2 Kitchens Hot Tub

Winston Sleeps 16 - 2 Kitchens Hot Tub
4.0 star property
Winston-Salem
The price is SAR 593
SAR 1,605 total
includes taxes & fees
21 Jul - 22 Jul
Winston Sleeps 16 - 2 Kitchens Hot Tub
1 bedroom, iron/ironing board, free WiFi, bed sheets

Cozy studio apartment

Cozy studio apartment
Winston-Salem
The price is SAR 169
SAR 403 total
includes taxes & fees
9 Jul - 10 Jul
Cozy studio apartment
1 bedroom

The Hot Tub Hideaway

The Hot Tub Hideaway
Winston-Salem
9.6 out of 10, Exceptional, (33 reviews)
"It was a good stay"
United States
Kim R.
The price is SAR 597
SAR 1,001 total
includes taxes & fees
5 Jul - 6 Jul
The Hot Tub Hideaway
Private kitchen

La Casita #3

La Casita #3
Winston-Salem
The price is SAR 271
SAR 33,324 total
includes taxes & fees
5 Jul - 6 Jul
La Casita #3
Smart TV, fireplace

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, (10 reviews)
"Wonderful way out very quiet. Everything you could need for a night or two stay would definitely come again."
United States
Jason M.
The price is SAR 537
SAR 968 total
includes taxes & fees
5 Jul - 6 Jul
Charming 2-bedroom cabin with WiFi in brilliant Winston-Salem
4 bedrooms, hypo-allergenic bedding, in-room safe, blackout drapes

Heated Pool King Bed Jacuzzi Bath Arcade

Heated Pool King Bed Jacuzzi Bath Arcade
4.5 star property
Winston-Salem
8.0 out of 10, Very Good, (1 review)
"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
The price is SAR 397
SAR 931 total
includes taxes & fees
9 Jul - 10 Jul
Heated Pool King Bed Jacuzzi Bath Arcade
Private kitchen

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
Exterior

The Red Door Cabin

The Red Door Cabin
Winston-Salem
10.0 out of 10, Exceptional, (24 reviews)
"Cute place. "
United States
Sue C.
The price is SAR 537
SAR 925 total
includes taxes & fees
4 Jul - 5 Jul
The Red Door Cabin
Fridge, microwave, oven, stovetop

Quiet, newly renovated. Near everything!

Quiet, newly renovated. Near everything!
Winston-Salem
9.8 out of 10, Exceptional, (29 reviews)
"Very nice comfortable place that is dog friendly, loved the back porch. Host was very responsive to communication."
United States
Rachel S.
The price is SAR 436
SAR 984 total
includes taxes & fees
3 Jul - 4 Jul
Quiet, newly renovated. Near everything!
Business Apartment | Private kitchen | Fridge, microwave, stovetop, dishwasher

The Ardmore Executive Suite

The Ardmore Executive Suite
4.0 star property
Winston-Salem
7.6 out of 10, Good, (5 reviews)
"Still very confused about payment process. Host asked me to send additional money on weird sources. But stay was great!"
United States
Daniel
The price is SAR 392
SAR 725 total
includes taxes & fees
5 Jul - 6 Jul
The Ardmore Executive Suite
Terrace/patio

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, (55 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.
The price is SAR 568
SAR 1,019 total
includes taxes & fees
6 Jul - 7 Jul
Cozy King Blue H2O Staycation , Stock Tank Pool, Hot Tub, Fire Pit Pets OK!
Fridge, microwave, oven, stovetop

2-bedroom cottage in Winston Salem

2-bedroom cottage in Winston Salem
Winston-Salem
9.6 out of 10, Exceptional, (4 reviews)
"Nice stay. Would recommend for your visit to the area."
United States
Charles G.
The price is SAR 469
SAR 1,086 total
includes taxes & fees
6 Jul - 7 Jul
2-bedroom cottage in Winston Salem
Interior

Urban Escape 3 Bed 2.5 Bath Near Wake Forest

Urban Escape 3 Bed 2.5 Bath Near Wake Forest
Winston-Salem
9.2 out of 10, Wonderful, (15 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
Fridge, microwave, oven, stovetop

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, (55 reviews)
"Very nice place to stay! "
United States
Kirby M.
The price is SAR 368
SAR 951 total
includes taxes & fees
3 Jul - 4 Jul
La Casita: A Cozy Retreat Near Wake Forest University"
Smart TV, fireplace, books, offices

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)
The price is SAR 372
SAR 914 total
includes taxes & fees
6 Jul - 7 Jul
High Ceilings | King Beds | 85” TV | Near Downtown
Fridge, microwave, oven, stovetop

Cozy 3BR Home Near Fairgrounds and Downtown

Cozy 3BR Home Near Fairgrounds and Downtown
Winston-Salem
8.0 out of 10, Very Good, (1 review)
"Overall, we had a good stay. The home looked exactly like the photos and comfortably accommodated our group during a difficult time with family. The space was clean and met our needs. My only concerns were that the glass panel/door in the shower was missing, which made the bathroom less functional than expected. I also submitted a request to update the reservation to allow up to 5 guests because we had family and friends stopping by while we were grieving, but I never received a response from...
United States
Jayceon
The price is SAR 372
SAR 981 total
includes taxes & fees
6 Jul - 7 Jul
Cozy 3BR Home Near Fairgrounds and Downtown
Fridge, microwave, oven, stovetop

Winston Salem 3Bd 2Ba GAME ROOM mins to Downtown

Winston Salem 3Bd 2Ba GAME ROOM mins to Downtown
Winston-Salem
9.2 out of 10, Wonderful, (16 reviews)
"We were there for a conference, so this location is ideal! So close to the convention center, comfortable, clean and spacious. We loved it!"
United States
Terrie H.
The price is SAR 507
SAR 1,230 total
includes taxes & fees
6 Jul - 7 Jul
Winston Salem 3Bd 2Ba GAME ROOM mins to Downtown
Terrace/patio

Luxury 3BR Townhome - Sleep 6

Luxury 3BR Townhome - Sleep 6
Winston-Salem
9.2 out of 10, Wonderful, (55 reviews)
"The amenities were great as was the location for us."
United States
jeanne k.
Luxury 3BR Townhome - Sleep 6
Fridge, microwave, oven, stovetop

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, (12 reviews)
"Host was very friendly - place was super clean and exactly as listed!"
United States
Brittany
The price is SAR 432
SAR 1,184 total
includes taxes & fees
9 Jul - 10 Jul
Charming 2-bed, 2 full bath lower level studio with WiFi, AC in Ardmore
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
"Was nice"
Moises 2-night trip
Posted 18 hours ago
Hawthorne Inn and Conference Center

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?

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 217 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.