Winston-Salem Vacation Rentals

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Check prices for these dates

In two weeks
Feb 20 - Feb 22
In two months
Apr 3 - Apr 5
In three months
May 1 - May 3
In four months
May 29 - May 31

Our top choices for Winston-Salem vacation rentals

2 bedrooms, desk, free WiFi, bed sheets

2-bedroom Goat Cottage in Winston-Salem

2-bedroom Goat Cottage in Winston-Salem
Winston-Salem
10.0 out of 10, Exceptional, (1 review)
"Host was very responsive! Place was clean and orderly, and goats were adorable! Would stay again."
United States
R S.
The price is ￥12,386
￥35,787 total
includes taxes & fees
Feb 8 - Feb 9
2-bedroom Goat Cottage in Winston-Salem
House | Private kitchen | Fridge, microwave, oven, stovetop

King Beds Hot Tub Arcade Grill & Firepit

King Beds Hot Tub Arcade Grill & Firepit
4.0 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 ￥21,636
￥47,966 total
includes taxes & fees
Feb 8 - Feb 9
King Beds Hot Tub Arcade Grill & Firepit
House (3 Bedrooms) | Interior

Cozy Cottage: Nature-filled Winston-salem Retreat!

Cozy Cottage: Nature-filled Winston-salem Retreat!
3.0 star property
Winston-Salem
The price is ￥27,750
￥74,325 total
includes taxes & fees
Feb 10 - Feb 11
Cozy Cottage: Nature-filled Winston-salem Retreat!
TV

Chic 2BR/2BA Near Dining & Shops

Chic 2BR/2BA Near Dining & Shops
Winston-Salem
9.0 out of 10, Wonderful, (4 reviews)
"This house is really fantastic- we had a great stay. Cozy with a great kitchen - ideal location walking distance to several wonderful local establishments with great food options - super nice bathrooms and seriously good space in the bedrooms. We look forward to staying again. "
United States
John L.
The price is ￥13,993
￥40,440 total
includes taxes & fees
Feb 8 - Feb 9
Chic 2BR/2BA Near Dining & Shops
4 bedrooms, hypo-allergenic bedding, in-room safe, blackout drapes

Heated Pool King Bed Jacuzzi Bath Arcade

Heated Pool King Bed Jacuzzi Bath Arcade
4.0 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 ￥36,687
￥61,597 total
includes taxes & fees
Feb 8 - Feb 9
Heated Pool King Bed Jacuzzi Bath Arcade
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
9.4 out of 10, Exceptional, (6 reviews)
"It was perfect for our needs! Ty so much for a great place to stay!"
United States
Bobby
The price is ￥22,435
￥40,413 total
includes taxes & fees
Feb 9 - Feb 10
Charming 2-bedroom cabin with WiFi in brilliant Winston-Salem
Dining

Downtown Charm, 3 Bdr, Near Rest and Bars

Downtown Charm, 3 Bdr, Near Rest and Bars
Winston-Salem
9.4 out of 10, Exceptional, (21 reviews)
"We had a fantastic stay in this very lovely home. The host was very communicative and we did not have any problems."
United States
Adam
The price is ￥13,993
￥39,840 total
includes taxes & fees
Feb 9 - Feb 10
Downtown Charm, 3 Bdr, Near Rest and Bars
Living area

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
Winston-Salem
9.0 out of 10, Wonderful, (4 reviews)
"We enjoyed our short stay, house is very cute and cozy and well put together "
United States
Anonymous traveler
The price is ￥12,699
￥34,723 total
includes taxes & fees
Feb 9 - Feb 10
Spacious 3-Bedroom with 4 beds, Fully Furnished Home Near Downtown Winston-Salem
Microwave, oven, stovetop, dishwasher

Rosewood Loft I Upper Suite

Rosewood Loft I Upper Suite
Winston-Salem
10.0 out of 10, Exceptional, (1 review)
"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.
The price is ￥22,890
￥49,784 total
includes taxes & fees
Feb 8 - Feb 9
Rosewood Loft I Upper Suite
Fridge, microwave, oven, stovetop

Quiet, newly renovated. Near everything!

Quiet, newly renovated. Near everything!
Winston-Salem
10.0 out of 10, Exceptional, (22 reviews)
"We loved this beautiful and clean unit! We stayed in the area for a wedding and it was perfect to fit many guests. Would stay again if we found ourselves back in the area. "
United States
Kate S.
The price is ￥18,186
￥41,280 total
includes taxes & fees
Feb 15 - Feb 16
Quiet, newly renovated. Near everything!
Fridge, microwave, dishwasher, ice maker

Minimalist Stay

Minimalist Stay
Winston-Salem
10.0 out of 10, Exceptional, (4 reviews)
"Wonderful stay…just what we needed "
United States
Patricia K.
Minimalist Stay
Interior

Cozy Stay Near DT w/Deck and Fenced Yard

Cozy Stay Near DT w/Deck and Fenced Yard
Winston-Salem
8.0 out of 10, Very Good, (2 reviews)
"Clean, quiwt, and close to everything. "
United States
Rebecca G.
The price is ￥16,932
￥27,105 total
includes taxes & fees
Feb 8 - Feb 9
Cozy Stay Near DT w/Deck and Fenced Yard
Fridge, microwave, oven, stovetop

Winston Salem 3Bd 2Ba GAME ROOM mins to Downtown

Winston Salem 3Bd 2Ba GAME ROOM mins to Downtown
Winston-Salem
9.6 out of 10, Exceptional, (9 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 ￥19,598
￥48,013 total
includes taxes & fees
Feb 8 - Feb 9
Winston Salem 3Bd 2Ba GAME ROOM mins to Downtown
Fridge, microwave, oven, stovetop

Winston Salem: Heated Pool, Arcade, & Jacuzzis

Winston Salem: Heated Pool, Arcade, & Jacuzzis
Winston-Salem
10.0 out of 10, Exceptional, (1 review)
"Pool was nice, well heated. "
United States
Silke N.
The price is ￥39,744
￥76,924 total
includes taxes & fees
Feb 8 - Feb 9
Winston Salem: Heated Pool, Arcade, & Jacuzzis
1 bedroom, iron/ironing board, free WiFi, bed sheets

Cozy Accessible Studio Near Wake Forest & Downtown Winston-Salem

Cozy Accessible Studio Near Wake Forest & Downtown Winston-Salem
Winston Salem
10.0 out of 10, Exceptional, (1 review)
"The room is clean, quiet, and cozy. I could tell my hosts had thought very carefully about what a guest may need, and they covered all those bases and more. Located in a quiet neighborhood very close to restaurants, grocery stores, etc."
United States
William L.
The price is ￥10,191
￥27,460 total
includes taxes & fees
Mar 8 - Mar 9
Cozy Accessible Studio Near Wake Forest & Downtown Winston-Salem
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 ￥11,037
￥28,416 total
includes taxes & fees
Feb 8 - Feb 9
La Casita #2 Great location,close to downtown Winston Salem 1 mile from UNCSA
Outdoor dining

La Casita .

La Casita .
Winston-Salem
The price is ￥10,661
￥27,993 total
includes taxes & fees
Feb 9 - Feb 10
La Casita .
Terrace/patio

Luxury 3BR Townhome - Sleep 6

Luxury 3BR Townhome - Sleep 6
Winston-Salem
9.4 out of 10, Exceptional, (45 reviews)
"Great hosts! Perfect for a family. Nice, quiet area. Convenient location."
United States
Mary
The price is ￥13,993
￥40,440 total
includes taxes & fees
Feb 9 - Feb 10
Luxury 3BR Townhome - Sleep 6
House | 5 bedrooms, hypo-allergenic bedding, laptop workspace

Arcade Kid Friendly Firepit Grill HotTub

Arcade Kid Friendly Firepit Grill HotTub
3.5 star property
Winston-Salem
The price is ￥18,625
￥60,240 total
includes taxes & fees
Feb 16 - Feb 17
Arcade Kid Friendly Firepit Grill HotTub
Exterior

3 King Beds Quiet Workspace Near Novant/Wake Forest

3 King Beds Quiet Workspace Near Novant/Wake Forest
Winston-Salem
The price is ￥16,901
￥52,300 total
includes taxes & fees
Mar 8 - Mar 9
3 King Beds Quiet Workspace Near Novant/Wake Forest
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

Comfort Suites Hanes Mall

Comfort Suites Hanes Mall

10/10 Excellent
"Comfort convenient and friendly people"
Tamara 1-night trip
Posted 2 days ago
Comfort Suites 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 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?

Southern Charm Meets City Comfort: This highly rated vacation home rental in Winston-Salem is located on a lake and offers a garden, air-conditioning, and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

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

Choose from 221 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.