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
Jul 24 - Jul 26
In two months
Sep 4 - Sep 6
In three months
Oct 2 - Oct 4
In four months
Oct 30 - Nov 1

Our top choices for Winston-Salem vacation rentals

1 bedroom, iron/ironing board, free WiFi, bed sheets

Cozy studio apartment

Cozy studio apartment
Winston-Salem
The price is ￥7,276
￥17,357 total
includes taxes & fees
Jul 18 - Jul 19
Cozy studio apartment
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 ￥43,169
￥87,458 total
includes taxes & fees
Jul 12 - Jul 13
Cozy Cottage: Nature-filled Winston-salem Retreat!
House | 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 ￥69,845
￥119,344 total
includes taxes & fees
Jul 22 - Jul 23
Arcade Kid Friendly Firepit Grill HotTub
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 ￥22,473
￥49,647 total
includes taxes & fees
Jul 12 - Jul 13
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 ￥28,646
￥72,627 total
includes taxes & fees
Jul 12 - Jul 13
Winston Sleeps 16 - 2 Kitchens Hot Tub
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 ￥42,781
￥69,111 total
includes taxes & fees
Jul 22 - Jul 23
Heated Pool King Bed Jacuzzi Bath Arcade
Smart TV, fireplace, table tennis, offices

Olde Towne Retreat | Pet-Friendly Family Retreat Near Campus

Olde Towne Retreat | Pet-Friendly Family Retreat Near Campus
Winston-Salem
The price is ￥29,878
￥236,090 total
includes taxes & fees
Aug 10 - Aug 11
Olde Towne Retreat | Pet-Friendly Family Retreat Near Campus
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, (11 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 ￥23,136
￥41,857 total
includes taxes & fees
Jul 12 - Jul 13
Charming 2-bedroom cabin with WiFi in brilliant Winston-Salem
WiFi

1980's ARCADE + 80's themed bedroom

1980's ARCADE + 80's themed bedroom
Winston-Salem
The price is ￥40,016
￥51,065 total
includes taxes & fees
Aug 10 - Aug 11
1980's ARCADE + 80's themed bedroom
Exterior

Winston/Kville w Park Arcade Fenced Yard

Winston/Kville w Park Arcade Fenced Yard
Winston-Salem
7.0 out of 10, Good, (4 reviews)
"Great location. Terrific fenced backyard for pets. Quiet neighborhood. Very kind host (Tawny)."
United States
Cathy L.
The price is ￥189,166
￥250,713 total
includes taxes & fees
Jul 24 - Jul 25
Winston/Kville w Park Arcade Fenced Yard
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 ￥18,755
￥43,120 total
includes taxes & fees
Jul 13 - Jul 14
Quiet, newly renovated. Near everything!
1 bedroom

The Hot Tub Hideaway

The Hot Tub Hideaway
Winston-Salem
9.6 out of 10, Exceptional, (34 reviews)
"It was a good stay"
United States
Kim R.
The price is ￥23,136
￥40,030 total
includes taxes & fees
Jul 12 - Jul 13
The Hot Tub Hideaway
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.
The price is ￥16,362
￥44,263 total
includes taxes & fees
Jul 12 - Jul 13
Luxury 3BR Townhome - Sleep 6
Smart TV, fireplace, foosball, books

Spacious 4-bedroom house with WiFi, AC in welcoming Winston-Salem, Ardmore

Spacious 4-bedroom house with WiFi, AC in welcoming Winston-Salem, Ardmore
Winston-Salem
10.0 out of 10, Exceptional, (23 reviews)
"The house was perfect for our long weekend. Great spaces and clean!"
United States
Kelly C.
The price is ￥36,378
￥79,475 total
includes taxes & fees
Aug 10 - Aug 11
Spacious 4-bedroom house with WiFi, AC in welcoming Winston-Salem, Ardmore
TV, video games

Spacious Historical Home 3 mins from Downtown

Spacious Historical Home 3 mins from Downtown
Winston-Salem
The price is ￥26,677
￥65,771 total
includes taxes & fees
Jul 14 - Jul 15
Spacious Historical Home 3 mins from Downtown
Interior

Hartman Casita! Quiet neighborhood.1 king Bed!

Hartman Casita! Quiet neighborhood.1 king Bed!
Winston-Salem
9.8 out of 10, Exceptional, (22 reviews)
"Great house"
United States
John M.
The price is ￥39,288
￥84,769 total
includes taxes & fees
Jul 12 - Jul 13
Hartman Casita! Quiet neighborhood.1 king Bed!
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 ￥15,570
￥40,616 total
includes taxes & fees
Jul 12 - Jul 13
La Casita: A Cozy Retreat Near Wake Forest University"
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 ￥19,499
￥45,602 total
includes taxes & fees
Aug 10 - Aug 11
LUX Home - Centrally Located - only minutes to Norvant Health & Historic Salem
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 ￥23,136
￥40,030 total
includes taxes & fees
Jul 12 - Jul 13
The Red Door Cabin
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 ￥21,827
￥53,348 total
includes taxes & fees
Jul 13 - Jul 14
Winston Salem 3Bd 2Ba GAME ROOM mins to Downtown
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

Hampton Inn Winston-Salem Hanes Mall

Hampton Inn Winston-Salem Hanes Mall

8/10 Good
"Price was a little high"
jeffery 1-night trip
Posted less than an hour ago
Hampton Inn Winston-Salem 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:

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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 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.