Winston-Salem Vacation Rentals

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Check prices for these dates

In two weeks
Apr 10 - Apr 12
In two months
May 22 - May 24
In three months
Jun 19 - Jun 21
In four months
Jul 17 - Jul 19

Our top choices for Winston-Salem vacation rentals

Fridge, microwave, oven, stovetop

Updated 1BR cottage on private acre+ lot

Updated 1BR cottage on private acre+ lot
Winston-Salem
10.0 out of 10, Exceptional, (19 reviews)
"Such a great place to stay. Everything we needed, we had. I would highly recommend this and would stay again. "
United States
Zack W.
The price is ￥7,522
￥20,485 total
includes taxes & fees
Mar 25 - Mar 26
Updated 1BR cottage on private acre+ lot
Outdoor dining

La Casita .

La Casita .
Winston-Salem
10.0 out of 10, Exceptional, (2 reviews)
"This house was perfect for our weekend in! The fenced yard made it so easy to have our fur babies with us. Everything was in great condition and the house had everything we needed. The host was very accommodating and responsive. We thoroughly enjoyed our stay and will gladly come back."
United States
Rachel U.
The price is ￥10,764
￥28,264 total
includes taxes & fees
Mar 30 - Mar 31
La Casita .
Fridge, microwave, oven, stovetop

Cozy 3BR Home Near Fairgrounds and Downtown

Cozy 3BR Home Near Fairgrounds and Downtown
Winston-Salem
The price is ￥13,297
￥37,590 total
includes taxes & fees
Mar 30 - Mar 31
Cozy 3BR Home Near Fairgrounds and Downtown
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 ￥12,356
￥30,156 total
includes taxes & fees
Mar 25 - Mar 26
La Casita #2 Great location,close to downtown Winston Salem 1 mile from UNCSA
Exterior

3 King Beds Quiet Workspace Near Novant/Wake Forest

3 King Beds Quiet Workspace Near Novant/Wake Forest
Winston-Salem
The price is ￥15,063
￥51,982 total
includes taxes & fees
Apr 1 - Apr 2
3 King Beds Quiet Workspace Near Novant/Wake Forest
Fridge, microwave, oven, stovetop

Quit, Cozy, Pet Friendly Condo

Quit, Cozy, Pet Friendly Condo
Winston-Salem
7.8 out of 10, Good, (8 reviews)
"It was sufficient for our short term lodging needs."
United States
Stephanie
The price is ￥9,554
￥34,188 total
includes taxes & fees
Mar 30 - Mar 31
Quit, Cozy, Pet Friendly Condo
Interior

Rosewood Loft I Lower Suite

Rosewood Loft I Lower Suite
Winston-Salem
The price is ￥16,305
￥35,420 total
includes taxes & fees
Apr 5 - Apr 6
Rosewood Loft I Lower Suite
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, (22 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 ￥16,954
￥43,240 total
includes taxes & fees
Apr 6 - Apr 7
Downtown Charm, 3 Bdr, Near Rest and Bars
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 ￥10,350
￥27,889 total
includes taxes & fees
Apr 13 - Apr 14
Cozy Accessible Studio Near Wake Forest & Downtown Winston-Salem
Property grounds

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

WEST END WHISPER 3 minute walk or drive to Everything. Prime location.
Winston-Salem
9.4 out of 10, Exceptional, (16 reviews)
"The host was very accommodating and always available to answer questions/concerns. The location is ideal. Coffee shops, restaurants and entertainment all in walking distance. Will definitely stay here again. "
United States
Joe L.
The price is ￥18,205
￥28,173 total
includes taxes & fees
Apr 2 - Apr 3
WEST END WHISPER 3 minute walk or drive to Everything. Prime location.
Fridge, microwave, oven, stovetop

3 King Beds | XL TVs | Near Hospital, College & DT

3 King Beds | XL TVs | Near Hospital, College & DT
Winston-Salem
8.4 out of 10, Very Good, (15 reviews)
"Great stay with family. "
United States
Tyler J.
The price is ￥13,375
￥34,976 total
includes taxes & fees
Apr 20 - Apr 21
3 King Beds | XL TVs | Near Hospital, College & DT
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 ￥17,871
￥43,939 total
includes taxes & fees
Mar 25 - Mar 26
King Beds Hot Tub Arcade Grill & Firepit
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, (52 reviews)
"Very nice place to stay! "
United States
Kirby M.
The price is ￥17,038
￥41,384 total
includes taxes & fees
Mar 25 - Mar 26
La Casita: A Cozy Retreat Near Wake Forest University"
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, (18 reviews)
"Wonderful stay! "
United States
Hannah J.
The price is ￥17,809
￥37,655 total
includes taxes & fees
Mar 31 - Apr 1
Log Cabin on Main St. In the ❤️ of Winston Salem. Sleeps 4 comfortably.
TV

Chic 2BR/2BA Near Dining & Shops

Chic 2BR/2BA Near Dining & Shops
Winston-Salem
9.4 out of 10, Exceptional, (6 reviews)
"Absolutely spotless and adorable cottage with tons of room, with a layout that makes it appear more spacious than its stated square footage. The decor is cozy and welcoming, with board games galore in the living room. Loved the spacious dining table with bench. Both showers are gigantic and tiled beautifully. We chose the dual-head shower in the spacious back bedroom, which easily holds 2 queen beds and furniture, as we chose to sleep there instead of the front bedroom. The mattress was very...
United States
Steven A.
The price is ￥14,128
￥40,653 total
includes taxes & fees
Mar 25 - Mar 26
Chic 2BR/2BA Near Dining & Shops
Terrace/patio

Luxury 3BR Townhome - Sleep 6

Luxury 3BR Townhome - Sleep 6
Winston-Salem
9.2 out of 10, Wonderful, (46 reviews)
"Excellent amenities. Very clean and we had wonderful stay. "
United States
Akiko C.
The price is ￥14,211
￥40,352 total
includes taxes & fees
Mar 31 - Apr 1
Luxury 3BR Townhome - Sleep 6
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 ￥30,077
￥77,247 total
includes taxes & fees
Mar 26 - Mar 27
Cozy Cottage: Nature-filled Winston-salem Retreat!
Smart TV, books

High Ceilings | King Beds | 85” TV | Near Downtown

High Ceilings | King Beds | 85” TV | Near Downtown
Winston-Salem
7.6 out of 10, Good, (15 reviews)
"Lovely and affordable apartment with incredibly attentive and responsive host. Would totally stay again!"
United States
Caleb W.
The price is ￥15,672
￥37,462 total
includes taxes & fees
Apr 21 - Apr 22
High Ceilings | King Beds | 85” TV | Near Downtown
TV, video games

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, (10 reviews)
"A very comfortable and spacious house with all the amenities you need!"
United States
Bethel S.
The price is ￥16,552
￥43,010 total
includes taxes & fees
Apr 1 - Apr 2
Urban Escape 3 Bed 2.5 Bath Near Wake Forest
Interior

Cozy Stay Near DT w/Deck and Fenced Yard

Cozy Stay Near DT w/Deck and Fenced Yard
Winston-Salem
9.2 out of 10, Wonderful, (5 reviews)
"Clean, quiwt, and close to everything. "
United States
Rebecca G.
The price is ￥17,096
￥27,368 total
includes taxes & fees
Mar 25 - Mar 26
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

Spark by Hilton Winston-Salem University

Spark by Hilton Winston-Salem University

10/10 Excellent
"Fine stay. Simple place. Clearly just renovated, but done in a decent way. I did hear a bit of noise both nights (dogs, kids), but nothing I couldn't sleep through."
Matthew 2-night trip
Posted 10 hours ago
Spark by Hilton Winston-Salem University

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?

Quiet, newly renovated. Near everything!: This Winston-Salem vacation home rental 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. Another good choice for your trip to Winston-Salem is The Sunrise! Close to Wake forest University. 2 King beds. Quiet neighborhood!.

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

Choose from 220 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.