Winston-Salem Holiday Rentals

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Check prices for these dates

In two weeks
12 Jun - 14 Jun
In two months
24 Jul - 26 Jul
In three months
21 Aug - 23 Aug
In four months
18 Sept - 20 Sept

Our top choices for Winston-Salem holiday rentals

Interior

Cozy Cottage: Nature-filled Winston-salem Retreat!

Cozy Cottage: Nature-filled Winston-salem Retreat!
3.0 star property
Winston-Salem
The price is HK$1,873
HK$4,235 total
includes taxes & fees
1 Jun - 2 Jun
Cozy Cottage: Nature-filled Winston-salem Retreat!
WiFi

1980's ARCADE + 80's themed bedroom

1980's ARCADE + 80's themed bedroom
Winston-Salem
1980's ARCADE + 80's themed bedroom
Private kitchen

King Beds Hot Tub Arcade Grill & Firepit

King Beds Hot Tub Arcade Grill & Firepit
4.5 star property
Winston-Salem
9.0 out of 10, Wonderful, (2 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 HK$838
HK$2,122 total
includes taxes & fees
4 Jun - 5 Jun
King Beds Hot Tub Arcade Grill & Firepit
5 bedrooms, hypo-allergenic bedding, laptop workspace

Arcade Kid Friendly Firepit Grill HotTub

Arcade Kid Friendly Firepit Grill HotTub
4.0 star property
Winston-Salem
The price is HK$1,693
HK$3,872 total
includes taxes & fees
7 Jun - 8 Jun
Arcade Kid Friendly Firepit Grill HotTub
TV, video games

Spacious Historical Home 3 mins from Downtown

Spacious Historical Home 3 mins from Downtown
Winston-Salem
The price is HK$1,136
HK$2,949 total
includes taxes & fees
2 Jun - 3 Jun
Spacious Historical Home 3 mins from Downtown
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, (9 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 HK$1,121
HK$2,020 total
includes taxes & fees
4 Jun - 5 Jun
Charming 2-bedroom cabin with WiFi in brilliant Winston-Salem
Fridge, microwave, oven, stovetop

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

Charming 4-bedroom house with AC and WiFi in wonderful Winston-Salem
Winston-Salem
8.4 out of 10, Very good, (6 reviews)
"Property had clean rooms, host was very responsive. Had a great stay and is in a quiet part of Winston Salem."
United States
Khalil C.
The price is HK$3,135
HK$7,013 total
includes taxes & fees
1 Jun - 2 Jun
Charming 4-bedroom house with AC and WiFi in wonderful Winston-Salem
Interior

Rosewood Loft I Lower Suite

Rosewood Loft I Lower Suite
Winston-Salem
The price is HK$807
HK$1,780 total
includes taxes & fees
2 Jun - 3 Jun
Rosewood Loft I Lower Suite
Fridge, microwave, oven, stovetop

Cozy 3BR Home Near Fairgrounds and Downtown

Cozy 3BR Home Near Fairgrounds and Downtown
Winston-Salem
The price is HK$741
HK$1,999 total
includes taxes & fees
1 Jun - 2 Jun
Cozy 3BR Home Near Fairgrounds and Downtown
Private kitchen

LUX Home - Centrally Located - only minutes to Norvant Health & Historic Salem

LUX Home - Centrally Located - only minutes to Norvant Health & Historic Salem
Winston-Salem
The price is HK$811
HK$2,032 total
includes taxes & fees
3 Jun - 4 Jun
LUX Home - Centrally Located - only minutes to Norvant Health & Historic Salem
Exterior

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.
The price is HK$882
HK$1,891 total
includes taxes & fees
1 Jun - 2 Jun
Log Cabin on Main St. In the ❤️ of Winston Salem. Sleeps 4 comfortably.
Interior

Hartman Casita! Quiet neighborhood.1 king Bed!

Hartman Casita! Quiet neighborhood.1 king Bed!
Winston-Salem
9.8 out of 10, Exceptional, (21 reviews)
"Great house"
United States
John M.
The price is HK$1,740
HK$3,924 total
includes taxes & fees
1 Jun - 2 Jun
Hartman Casita! Quiet neighborhood.1 king Bed!
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
The price is HK$621
HK$1,498 total
includes taxes & fees
2 Jun - 3 Jun
La Casita #2 Great location,close to downtown Winston Salem 1 mile from UNCSA
Smart TV, fireplace

The Sunrise! Close to Wake forest University. 2 King beds. Quiet neighborhood!

The Sunrise! Close to Wake forest University. 2 King beds. Quiet neighborhood!
Winston-Salem
9.8 out of 10, Exceptional, (38 reviews)
"Perfect size, very clean and great location!"
United States
Laron A.
The price is HK$1,505
HK$3,772 total
includes taxes & fees
15 Jun - 16 Jun
The Sunrise! Close to Wake forest University. 2 King beds. Quiet neighborhood!
Interior

Cozy Cottage: Nature-Filled Winston-Salem Retreat!

Cozy Cottage: Nature-Filled Winston-Salem Retreat!
Winston-Salem
10.0 out of 10, Exceptional, (3 reviews)
"Our only regret was that we didn’t find Jennifer four years ago! We came to W-S to attend the WFU graduation. After spending four years at all of the different W-S hotels, this was a beautiful and relaxing change of pace to come home to every evening.There is just such an overwhelming peacefulness to be able to make your own cup of coffee and sit out on the deck after having a restful night sleep that is priceless."
United States
carolyne
The price is HK$1,669
HK$4,313 total
includes taxes & fees
1 Jun - 2 Jun
Cozy Cottage: Nature-Filled Winston-Salem Retreat!
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 HK$901
HK$2,426 total
includes taxes & fees
8 Jun - 9 Jun
Charming 2-bed, 2 full bath lower level studio with WiFi, AC in Ardmore
Terrace/patio

Luxury 3BR Townhome - Sleep 6

Luxury 3BR Townhome - Sleep 6
Winston-Salem
9.2 out of 10, Wonderful, (50 reviews)
"The amenities were great as was the location for us."
United States
jeanne k.
The price is HK$872
HK$2,164 total
includes taxes & fees
3 Jun - 4 Jun
Luxury 3BR Townhome - Sleep 6
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, (14 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 HK$1,058
HK$2,568 total
includes taxes & fees
1 Jun - 2 Jun
Winston Salem 3Bd 2Ba GAME ROOM mins to Downtown
Interior

Cozy Stay Near DT w/Deck and Fenced Yard

Cozy Stay Near DT w/Deck and Fenced Yard
Winston-Salem
9.6 out of 10, Exceptional, (8 reviews)
"Great place to stay!"
United States
Jessica C.
The price is HK$846
HK$1,399 total
includes taxes & fees
1 Jun - 2 Jun
Cozy Stay Near DT w/Deck and Fenced Yard
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

Sleep Inn Hanes Mall

Sleep Inn Hanes Mall

10/10 Excellent
"Met my expectations"
Thomas 3-night trip
Posted 9 hours ago
Sleep Inn Hanes Mall

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

Frequently asked questions

Can I find holiday rentals in Winston-Salem?

Yes, there are holiday rentals in Winston-Salem close to Adventure Landing Winston-Salem, or you can select a more secluded option if you're looking for a relaxing stay. Visitors like the array of shops and lush forest in Winston-Salem. Make sure to also enjoy the university campus and top-notch restaurants during your holiday.

What are some of the best holiday rentals that Winston-Salem has to offer?

La Casita .: This highly rated holiday home rental in Winston-Salem is equipped with a patio, air conditioning and laundry facilities to help you feel comfortable during your stay. Another good choice for your trip to Winston-Salem is Quiet, newly renovated. Near everything!.

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

Choose from 219 Expedia holiday rentals in Winston-Salem for a memorable holiday.

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 holiday rentals like in Winston-Salem?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Winston-Salem. Holiday rentals feature amenities such as patios, hot tubs and fire pits so you'll have all the conveniences of home. If you're concerned about cleanliness, holiday rentals can offer a sense of security away from public hotel lifts and busy front desks while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a great option for a family getaway.