Winston-Salem holiday rentals

We found 583 holiday rentals — enter your dates for availability
Find the perfect place for you stay in Winston-Salem by choosing from 210 houses, 85 apartments and other holiday rentals. Holiday rentals provide the best amenities for your family, friends or furry companion, such as Wi-Fi and a washer and dryer. You'll be able to choose a property to rent for everyone's needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts – Winston-Salem

Showing deals for:15 Jan - 22 Jan

Kitchen
Grand Room at night!
Study
Study
Exceptional
(16 reviews)

Stunning Penthouse 15-B Located In Historic Market Square.

High Point

8% off
S$11,054
for 7 nights, 1 home
S$1,579 per night
includes taxes & fees
Stunning Penthouse 15-B Located In Historic Market Square.
Exterior
Exterior
Exterior
Exterior detail
Exceptional
(12 reviews)

Luxurious Cape Cod in Emerywood - Minutes to Furniture Market & HP University

High Point

7% off
S$4,257
for 7 nights, 1 home
S$608 per night
includes taxes & fees
Luxurious Cape Cod in Emerywood - Minutes to Furniture Market & HP University
Room
Living area
Living area
Dining
Exceptional
(16 reviews)

Charming 3-bedroom cottage centrally located to enjoy High Point.

High Point

7% off
S$1,682
for 7 nights, 1 cottage
S$240 per night
includes taxes & fees
Charming 3-bedroom cottage centrally located to enjoy High Point.
Room
Private kitchen
Living area
Living area
Exceptional
(8 reviews)

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

Kernersville

7% off
S$1,718
for 7 nights, 1 home
S$245 per night
includes taxes & fees
Charming 4-bedroom house with AC and WiFi in Winston-Salem
Welcome to Eagle`s Landing! We love sitting on our front porch to enjoy the beautiful NC weather!
We are 1 block from the New High Point Children`s Museum.
Large kitchen that is perfect for gathering and/or cooking a large meal.
Large kitchen that is perfect for gathering and/or cooking a large meal.
Exceptional
(14 reviews)

New Build! Close to HPU & Furniture Market

High Point

7% off
S$2,238
for 7 nights, 1 home
S$320 per night
includes taxes & fees
New Build! Close to HPU & Furniture Market
Private kitchen
Private kitchen
Living area
Private kitchen
Exceptional
(9 reviews)

Modern/Retro 2br Condo by Exceptional Stays

High Point

15% off
S$2,181
for 7 nights, 1 apartment
S$312 per night
includes taxes & fees
Modern/Retro 2br Condo by Exceptional Stays
Private kitchen
Living area
Interior
Exterior
Exceptional
(13 reviews)

Charming 2-bedroom cabin with WiFi in brilliant Winston-Salem

Winston-Salem

8% off
S$1,732
for 7 nights, 1 cabin
S$247 per night
includes taxes & fees
Charming 2-bedroom cabin with WiFi in brilliant Winston-Salem
Living area
Pool
Private kitchen
Terrace/patio
Wonderful
(30 reviews)

Private & Spacious 4BR w/ Heated Pool, Hot Tub & Fire Pit - Near HPU & Market

High Point

5% off
S$4,334
for 7 nights, 1 home
S$619 per night
includes taxes & fees
Private & Spacious 4BR w/ Heated Pool, Hot Tub & Fire Pit - Near HPU & Market
King Bedroom (Upstairs)
Living room with so much natural light and vaulted ceilings.
Private entrance
Kitchen with stainless steel appliances
Exceptional
(5 reviews)

Conveniently located High Point Townhome

High Point

6% off
S$1,957
for 7 nights, 1 home
S$280 per night
includes taxes & fees
Conveniently located High Point Townhome
Interior
Private kitchen
Interior
Dining
Wonderful
(12 reviews)

Spacious Townhouse In High Point Near HPU & Furniture Market

High Point

7% off
S$1,352
for 7 nights, 1 home
S$193 per night
includes taxes & fees
Spacious Townhouse In High Point Near HPU & Furniture Market
Exterior
Private kitchen
Interior
Property grounds
Exceptional
(14 reviews)

Spacious 4-bedroom house in charming Winston-Salem with WiFi and fenced in yard.

Winston-Salem

10% off
S$2,678
for 7 nights, 1 home
S$383 per night
includes taxes & fees
Spacious 4-bedroom house in charming Winston-Salem with WiFi and fenced in yard.
Dining
Living area
Exterior
Private kitchen
Exceptional
(7 reviews)

Cozy Cottage minutes to Downtown

Winston-Salem

7% off
S$1,707
for 7 nights, 1 cottage
S$244 per night
includes taxes & fees
Cozy Cottage minutes to Downtown
Living area
Dining
Living area
Private kitchen
Exceptional
(11 reviews)

Cheerful cottage w/work space near hospitals

Winston-Salem

7% off
S$1,927
for 7 nights, 1 home
S$275 per night
includes taxes & fees
Cheerful cottage w/work space near hospitals
Private kitchen
Room
Exterior
Interior
Exceptional
(12 reviews)

Luxury Cottage. 2 King Suites. Walk Downtown & Old Salem

Winston-Salem

8% off
S$3,270
for 7 nights, 1 cottage
S$467 per night
includes taxes & fees
Luxury Cottage. 2 King Suites. Walk Downtown & Old Salem
Outdoor dining
Private kitchen
Exterior
Living area
Exceptional
(7 reviews)

Beautiful Farm and Barndo Loft in Kernersville with WiFi and AC

Kernersville

7% off
S$1,333
for 7 nights, 1 home
S$190 per night
includes taxes & fees
Beautiful Farm and Barndo Loft in Kernersville with WiFi and AC
Business centre
Interior
Room
Interior
Very good
(15 reviews)

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

Winston-Salem

5% off
S$1,191
for 7 nights, 1 home
S$170 per night
includes taxes & fees
3 King Beds | XL TVs | Near Hospital, College & DT
Private kitchen
Nighttime under the stars
Interior
Dining
Exceptional
(66 reviews)

Elegant Pet Friendly Ranch Home close to everything!

Winston-Salem

7% off
S$2,458
for 7 nights, 1 home
S$351 per night
includes taxes & fees
Elegant Pet Friendly Ranch Home close to everything!
Room
Living area
Exterior
Private kitchen
Wonderful
(14 reviews)

Cozy 2BR King Bed Sleeps 6 Near Hospital & Wake Forest

Winston-Salem

7% off
S$1,454
for 7 nights, 1 home
S$208 per night
includes taxes & fees
Cozy 2BR King Bed Sleeps 6 Near Hospital & Wake Forest
Master Bedroom Upstairs
Interior
Dining Room
Exterior
Exceptional
(13 reviews)

Full of Character and Convenient to Downtown and HPU.

High Point

19% off
S$1,761
for 7 nights, 1 home
S$252 per night
includes taxes & fees
Full of Character and Convenient to Downtown and HPU.
Dining table, connected to kitchen
Kitchen, with full amenities, access to back deck
Entryway, leads to living room
Entryway to primary guest bathroom
Exceptional
(16 reviews)

Stunning 3 Bedroom Retreat with Inspiring Backyard

High Point

11% off
S$2,625
for 7 nights, 1 home
S$375 per night
includes taxes & fees
Stunning 3 Bedroom Retreat with Inspiring Backyard
Property grounds
Property grounds
Room
Living Room
Exceptional
(80 reviews)

Historic Craftsman bungalow near Winston Salem, wineries and mountain activities

Rural Hall

12% off
S$1,503
for 7 nights, 1 home
S$215 per night
includes taxes & fees
Historic Craftsman bungalow near Winston Salem, wineries and mountain activities
Games room
Living room, overlooks the front yard with beautiful natural light
Dining
Living room
Exceptional
(6 reviews)

Cozy Pet Friendly 3BR - Fenced Yard - 1Mi HPU & DwnTwn - Furniture Market

High Point

7% off
S$1,673
for 7 nights, 1 home
S$239 per night
includes taxes & fees
Cozy Pet Friendly 3BR - Fenced Yard - 1Mi HPU & DwnTwn - Furniture Market
Interior
Private kitchen
Room
Dining
Wonderful
(49 reviews)

Sleeps 6 - 3 Queen Beds - 2 Mi Wake Forest + Hospital

Winston-Salem

7% off
S$1,552
for 7 nights, 1 home
S$222 per night
includes taxes & fees
Sleeps 6 - 3 Queen Beds - 2 Mi Wake Forest + Hospital
  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

The lush setting of Winston-Salem is ready to explore

The area's art galleries and museums are just some of the reasons to come on holiday to Winston-Salem. Renowned for its sporting events, shopping and forests, this city welcomes all visitors. Many of our holiday rentals offer full kitchens, spacious living quarters and sometimes even a hot tub—perfect for a relaxing getaway.

Activities and attractions in Winston-Salem

Are you hoping to discover attractions to visit in the area? Venture out of your cosy holiday rental and check out everything that makes Winston-Salem a one-of-a-kind holiday spot. These are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Medaloni Cellars and Vinyards (14 mi / 22.5 km)
  • Divine Llama Vineyards (15.1 mi / 24.4 km)
  • Cellar 4201 Vineyard (16 mi / 25.7 km)
  • Richard Childress Vineyards (17.9 mi / 28.9 km)
  • Farmington Dragway (18.8 mi / 30.2 km)
  • Celebration Station (19.8 mi / 31.9 km)

Exploring the natural landscape of Winston-Salem

Whether you're looking for fun outdoor activities or just want to spend some time taking in the scenery, Winston-Salem is a great place to spend some time outside. Here are some of the area’s most enchanting natural features, all within 30 miles (48.2 km) of the city centre:

  • Reynolda Gardens (2.9 mi / 4.6 km)
  • Salem Lake (3.6 mi / 5.7 km)
  • Tanglewood Park (11.4 mi / 18.4 km)
  • Truist Sports Park (11.5 mi / 18.6 km)
  • BB&T Soccer Park (11.6 mi / 18.7 km)
  • Belews Lake Park (14.4 mi / 23.2 km)

Transport to and around Winston-Salem

Fly into Winston-Salem, NC (INT-Smith Reynolds), the closest airport, located 2.7 mi (4.4 km) from the city centre. If you can't find a flight that's convenient for your trip, you could also fly into Greensboro, NC (GSO-Piedmont Triad Intl.), which is 17.1 mi (27.6 km) away.

Frequently asked questions

What is the most popular type of holiday rental accommodation in Winston-Salem?
Apartments are the most popular kind of holiday rental in Winston-Salem, according to our data. Even if you have a different vision in mind, Vrbo has properties in all shapes and sizes. Browse our options to find your ideal match.
How much does it cost to rent a holiday rental in Winston-Salem?
Length of stay, season and property type are some things that can affect the price of a holiday home. Simply enter your travel dates to find your dream escape. From comfy cottages to plush villas, all Vrbo holiday rentals offer amazing value.
How much does it cost to rent a beach house in Winston-Salem?
When you travel and the size and style of the property will influence how much you'll pay for your beachside escape. Enter your Winston-Salem travel dates to see all your options on Vrbo. Can't live without a private pool? Use our filters to choose the features and amenities you want in your beach house.
Are there pet-friendly holiday rentals in Winston-Salem?
Pack a suitcase for the pup in your life because Winston-Salem has 12 properties that put out the welcome mat to pets. Let your four-legged buddy have fun with the family at one of our pet-friendly holiday rentals on Vrbo. Simply enter your travel dates and destination, then check the "Pets allowed" filter box.
What are popular rental amenities in Winston-Salem?
Some of the most popular rental amenities people look for in Winston-Salem are nearby museums, a swimming pool and a barbecue grill. Whether you're on a trip with pals, family or even pets, Vrbo holiday homes come with the best amenities for starting a new adventure with the people that matter most.
Are there large group holiday rentals in Winston-Salem?
Take your pick of three Vrbo holiday rentals in Winston-Salem that can accommodate five or more guests. You'll enjoy all the room and privacy you need to spend time with your nearest and dearest — and nobody else.
Are there holiday rentals in Winston-Salem that welcome kids?
Gather your whole family for an unforgettable adventure in Winston-Salem at one of our 12 family-friendly holiday homes. A lot of these stays provide amenities that are just perfect for getaways with youngsters, such as full kitchens, extra bedrooms and private pools. Just click on the "Properties good for families" filter and choose your favourite option.
What are the top attractions for families in Winston-Salem?
Keep the kids amused at these awesome family-friendly attractions in Winston-Salem:
  • Airbound Trampoline Park
  • SciWorks
  • Old Salem
Are there one-bedroom holiday rentals in Winston-Salem?
Yes, there are four one-bedroom properties in Winston-Salem to select from. A one-bedroom holiday rental is a superb choice if it's just you and your sweetheart or if you're travelling on your own. Add in more space, privacy and convenience compared to a regular hotel, and you're sure to have an unforgettable getaway.
Can I find two-bedroom holiday rentals in Winston-Salem?
Gather your loved ones and enjoy a relaxing escape in one of the three two-bedroom holiday properties Winston-Salem has to offer.
Are there holiday rentals with WiFi in Winston-Salem?
Winston-Salem has three holiday rentals with WiFi, so you'll be able to stay connected while on holiday. Simply check the "WiFi" box in our handy search filter for a list of properties with this feature. From streaming movie blockbusters to updating your social media, these Vrbo homes make it a cinch to get online.
How can I find holiday rentals with air conditioning in Winston-Salem?
Work out your travel dates and then use our filter tool to search for holiday rentals with ac in Winston-Salem on Vrbo. With 12 air-conditioned properties available, you can enjoy a cool and comfortable trip.
How old do you have to be to rent a holiday rental in Winston-Salem?
The age limit can vary across properties on Vrbo, so look at the rules of the holiday home in Winston-Salem you want. But normally, it's 16, 18 or 21.
How long can I rent a holiday rental in Winston-Salem for?
It's really down to the Winston-Salem property. To view a list of options offering extended stays, simply type your dates and number of people into the Vrbo search page. Look forward to having the whole property to yourself, along with home comforts like a full kitchen, air conditioning and an outdoor space where the little ones can play. Keep your eyes peeled for long-term stays that offer weekly or monthly discounts.

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