Vacation rentals in Winston-Salem - HomeToGo base64Hash Vacation rentals in Winston-Salem - HomeToGo

Vacation rentals in Winston-Salem

Browse 1,133 available vacation homes and compared across 9 trusted partners
Anytime
Guests
Anytime
Guests

  • Price per night

    • Up to $100
    • $100 - $199
    • From $200

  • Accommodation types

    • Condo
    • House
    • Apartment

  • Distance to center

    • 2 mi
    • 3 mi
    • Any

  • Rating

    • 4.5+
    • 4+

  • Services

    • WiFi
    • Pool
    • Kitchen
    • TV
    • Air conditioning
    • Washing machine
    • Hot tub
    • Parking
    • Yard
    • Microwave
    • Balcony/patio
    • Dishwasher
    • Fireplace
    • Crib
    Show more

  • Accommodation type

    • Pet-friendly
    • No smoking
    • Wheelchair access
    • No pets

  • Activities

    • Grill
    • Fishing

Top 15 most Recommended Vacation Rentals in Winston-Salem

Discover your ideal Winston-Salem vacation rental with real-time comparisons of 1,133 properties, featuring recommended options based on the property location, value for money, and verified guest reviews.

Apartment Winston-Salem
Apartment ∙ 4 guests ∙ 2 bedrooms

Rental apartment with pool

Winston-Salem, Winston, North Carolina, United States
This family-friendly apartment in Winston-Salem features a pool and a kitchen, perfect for a memorable getaway with friends or family.
from $200
per night
Very good(4 ratings)
from $200
per night
View deal
House Winston-Salem
House ∙ 4 guests ∙ 2 bedrooms

House with terrace & BBQ | Nature view | Suitable for remote work

Winston-Salem, Winston, North Carolina, United States
This house rental in Winston-Salem features a fireplace, kitchen, and parking, perfect for a cozy getaway for four.
from $129
per night
Outstanding(57 ratings)
from $129
per night
View deal
Apartment Downtown Winston-Salem
Apartment ∙ 4 guests ∙ 2 bedrooms

Apartment with garden & terrace | Nature view

Downtown Winston-Salem, Winston-Salem, North Carolina, United States
from $101
per night
Outstanding(173 ratings)
from $101
per night
View deal
Apartment Winston-Salem
Apartment ∙ 4 guests ∙ 2 bedrooms

Apartment with yard & patio | City view

Winston-Salem, Winston, North Carolina, United States
This apartment in Winston-Salem features a kitchen and parking, accommodating up to four guests for a perfect getaway.
from $119
per night
Outstanding(145 ratings)
from $119
per night
View deal
House Winston-Salem
House ∙ 8 guests ∙ 4 bedrooms

House with terrace & yard | Good for workation

Winston-Salem, Winston, North Carolina, United States
This house rental in Winston-Salem features a fireplace, kitchen, and yard, perfect for family gatherings with parking for all.
from $161
per night
Outstanding(32 ratings)
from $161
per night
View deal
House Winston-Salem
House ∙ 2 guests ∙ 1 bedroom

Family-friendly wonderful vacation home with yard, grill & private pool | City view | Perfect for remote work | Pet-friendly

Winston-Salem, Winston, North Carolina, United States
This Winston-Salem house rental features a private pool, hot tub, and yard, perfect for a memorable getaway with pets.
from $151
per night
Outstanding(82 ratings)
from $151
per night
View deal
Apartment Winston-Salem
Apartment ∙ 2 guests ∙ 1 bedroom

Fully equipped charming rental apartment with yard

Winston-Salem, Winston, North Carolina, United States
This Winston-Salem apartment rental features a kitchen, yard, and parking, perfect for a getaway with a partner.
from $120
per night
Outstanding(122 ratings)
from $120
per night
View deal
House Winston-Salem
House ∙ 12 guests ∙ 5 bedrooms

Vacation home with barbeque, garden & patio | Nature view | Perfect for remote work

Winston-Salem, Winston, North Carolina, United States
This Winston-Salem house rental offers a yard, kitchen, and fireplace, accommodating up to 12 guests and pets for a memorable stay.
from $556
per night
Outstanding(58 ratings)
from $556
per night
View deal
House Winston-Salem
House ∙ 11 guests ∙ 4 bedrooms

House with patio, grill & garden

Winston-Salem, Winston, North Carolina, United States
from $327
per night
Outstanding(69 ratings)
from $327
per night
View deal
House Winston-Salem
House ∙ 9 guests ∙ 4 bedrooms

Children-friendly vacation home with terrace, yard & BBQ | Suitable for remote work | Pet-friendly

Winston-Salem, Winston, North Carolina, United States
This house rental in Winston-Salem features a yard, fireplace, and kitchen, accommodating up to 9 guests and pets.
from $248
per night
Outstanding(25 ratings)
from $248
per night
View deal
House Winston-Salem
House ∙ 12 guests ∙ 6 bedrooms

Family-oriented spacious vacation home with yard, sauna & jacuzzi | Pets allowed

Winston-Salem, Winston, North Carolina, United States
This Winston-Salem house rental offers a heated pool, hot tub, sauna, and spacious yard, perfect for families and pets.
from $869
per night
Outstanding(6 ratings)
from $869
per night
View deal
Apartment Winston-Salem
Apartment ∙ 4 guests ∙ 2 bedrooms

Child-friendly rental apartment

Winston-Salem, Winston, North Carolina, United States
This Winston-Salem apartment rental features a fireplace, kitchen, and parking, perfect for a family getaway for up to four.
from $170
per night
Excellent(31 ratings)
from $170
per night
View deal
House Winston-Salem
House ∙ 8 guests ∙ 4 bedrooms

Vacation home with barbeque

Winston-Salem, Winston, North Carolina, United States
A welcoming house rental in Winston-Salem, featuring a kitchen, family-friendly layout, and parking for up to eight guests.
from $231
per night
from $231
per night
View deal
Apartment Winston-Salem
Apartment ∙ 4 guests ∙ 2 bedrooms

Family-oriented rental apartment

Winston-Salem, Winston, North Carolina, United States
This Winston-Salem apartment offers a kitchen, family-friendly space, and parking, perfect for a memorable getaway for four.
from $147
per night
Outstanding(21 ratings)
from $147
per night
View deal
House Winston-Salem
House ∙ 6 guests ∙ 3 bedrooms

Child-friendly beautiful vacation home with barbecue, patio & garden

Winston-Salem, Winston, North Carolina, United States
This house rental in Winston-Salem features a kitchen, yard, and parking, perfect for a family getaway with space for six.
from $387
per night
Outstanding(97 ratings)
from $387
per night
View deal

Vacation rentals with a balcony

House Winston-Salem
from $283
per night
House ∙ 10 guests ∙ 5 bedrooms

Vacation home with grill, patio & yard | Perfect for remote work

4.9
Outstanding(100 ratings)
Winston-Salem, Winston, North Carolina, United States
Balcony
View deal
House Winston-Salem
from $198
per night
House ∙ 4 guests ∙ 2 bedrooms

Vacation home with patio & yard | Nature view

5.0
Outstanding(70 ratings)
Winston-Salem, Winston, North Carolina, United States
Balcony
View deal
Cabin Winston-Salem
from $180
per night
Cabin ∙ 3 guests ∙ 1 bedroom

Cabin with patio | Pet-friendly

5.0
Outstanding(54 ratings)
Winston-Salem, Winston, North Carolina, United States
Balcony
View deal
See all offers

Vacation Rentals With Fireplaces

House Winston-Salem
from $259
per night
House ∙ 10 guests ∙ 5 bedrooms

Children-friendly beautiful vacation home | City view | Suitable for remote work

5.0
Outstanding(65 ratings)
Winston-Salem, Winston, North Carolina, United States
Fireplace
View deal
House Winston-Salem
from $163
per night
House ∙ 6 guests ∙ 3 bedrooms

Vacation home with BBQ, patio & garden | City view | Suitable for remote work

5.0
Outstanding(30 ratings)
Winston-Salem, Winston, North Carolina, United States
Fireplace
View deal
House Winston-Salem
from $236
per night
House ∙ 8 guests ∙ 4 bedrooms

Fully equipped wonderful vacation home with barbeque & yard | Perfect for remote work | Pet-friendly

5.0
Outstanding(11 ratings)
Winston-Salem, Winston, North Carolina, United States
Fireplace
View deal
See all offers

Vacation rentals and apartments with air conditioning

House Winston-Salem
from $535
per night
House ∙ 8 guests ∙ 3 bedrooms

Vacation home with patio & garden

4.9
Outstanding(39 ratings)
Winston-Salem, Winston, North Carolina, United States
Air conditioning
View deal
Condo Winston-Salem
from $153
per night
Condo ∙ 4 guests ∙ 2 bedrooms

Fully equipped pleasant condo | Perfect for remote work

4.9
Outstanding(39 ratings)
Winston-Salem, Winston, North Carolina, United States
Air conditioning
View deal
House Winston-Salem
from $168
per night
House ∙ 5 guests ∙ 3 bedrooms

Family-friendly house with yard & terrace | Good for workation

4.9
Outstanding(25 ratings)
Winston-Salem, Winston, North Carolina, United States
Air conditioning
View deal
See all offers

Budget-friendly rental options

Enjoy affordable vacation rentals in Winston-Salem offering exceptional value for money

House Winston-Salem
from $223
per night
House ∙ 12 guests ∙ 4 bedrooms

Children-friendly house with terrace | Pets allowed

5.0
Outstanding(53 ratings)
Winston-Salem, Winston, North Carolina, United States
View deal
House Winston-Salem
from $141
per night
House ∙ 4 guests ∙ 2 bedrooms

Fully equipped charming vacation home with barbeque | Pets are welcome

5.0
Outstanding(30 ratings)
Winston-Salem, Winston, North Carolina, United States
View deal
House Winston-Salem
from $204
per night
House ∙ 11 guests ∙ 4 bedrooms

Fully equipped house with grill & patio | Perfect for remote work | Pets allowed

4.9
Outstanding(32 ratings)
Winston-Salem, Winston, North Carolina, United States
View deal

Top-Rated Vacation rentals in Winston-Salem

Book the highest-rated Winston-Salem vacation rentals, rated by real guests for comfort, location, cleanliness, services and value for money

House Winston-Salem
from $220
per night
House ∙ 8 guests ∙ 3 bedrooms

House with 3 rooms for 8 persons

4.8
Outstanding(145 ratings)
Winston-Salem, Winston, North Carolina, United States
View deal
House Winston-Salem
from $134
per night
House ∙ 6 guests ∙ 3 bedrooms

Fully equipped wonderful house with garden & BBQ | Perfect for remote work | Pets are welcome

4.7
Excellent(74 ratings)
Winston-Salem, Winston, North Carolina, United States
View deal
House Winston-Salem
from $509
per night
House ∙ 10 guests ∙ 6 bedrooms

Child-friendly vacation home with grill, terrace & yard | Nature view | Good for workation

5.0
Outstanding(31 ratings)
Winston-Salem, Winston, North Carolina, United States
View deal

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Verified reviews

Verified reviews

Trust in the quality and comfort of your stay with verified guest reviews.

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Price clarity, no surprises

Spend your budget exactly as planned by comparing thousands of providers.

Smart search made simple

Smart search made simple

Transform vacation planning into a joy with advanced, AI-powered search tools.

Find your dream stay

Find your dream stay

Explore 15 million+ rentals, the world’s biggest selection of vacation homes.

Popular Features & Amenities in Winston-Salem

  • Pet-friendly (381)
  • WiFi (982)
  • Pool (393)
  • Kitchen (490)
  • TV (935)
  • Air conditioning (1,029)
  • Washing machine (533)
  • Hot tub (38)
  • Parking (55)
  • No smoking (978)
  • Yard (266)
  • Microwave (749)

You will find a great selection of vacation rentals to book if you are looking for a property offering a pool in Winston-Salem. Hotel room with pools in Winston-Salem are a great option for groups of 10 and usually cost around $196 a night. You can also rent an accommodation providing a pool near the water, which is the case for many of the rentals in this destination.

Family-Friendly Vacation rentals in Winston-Salem Steeped in History but Close to the Action

A Winston-Salem vacation rental suits anybody wanting the comforts of home while enjoying Winston-Salem’s fun annual events, historic Old Salem attractions, or entertaining the kids outdoors or in.

Winston-Salem is a city steeped in history and heritage, and it has the landmarks to match. From Moravian cookies and George Washington’s 18th-century watering hole to world-class tennis and breathtaking state parks, Winston-Salem house rentals opens up a world of opportunities for families and independent travelers alike. Ranging from grand suburban period homes to stylish inner-city condos right in the heart of Downtown, a Winston-Salem vacation rental can cater to any style, group size, or budget. Keep an eye out to see if any of Winston-Salem’s fabulous festivals are taking place when you’re in town.

What are the best activities for families in Winston-Salem?

Science, Nature, Animals, and the Outdoors: Family-friendly Activities Around Winston-Salem

A Winston-Salem house rental is a great base for fun family adventures with kids. Learn while having fun at the acclaimed Kaleideum, a hands-on science center and nature park with locations in Downtown and northern Winston-Salem.

Tanglewood Park is another fabulous place to visit with children of all ages. This huge recreation center offers paddleboat rides, fishing, a waterpark, heritage steam train rides, and animal encounters. There’s also the beautiful Tanglewood Park Arboretum and Rose Garden to explore, and the popular Tanglewood Festival of Lights takes place every winter.

For active families who like the outdoors, both Pilot Mountain State Park and Hanging Rock State Park are within an hour’s drive of Winston-Salem. Hanging Rock offers three different hiking trails up to a breathtaking waterfall, or you can choose more challenging hiking, cycling and rock climbing routes at Pilot Mountain. If you need the kids to burn off some energy, Safari Nation Winston-Salem or the Rockin’ Jump Trampoline Park are sure to fit the bill.

What are the must-see attractions in Winston-Salem?

Get a Feel for Winston-Salem’s Rich Heritage

Drink With the Ghost of George Washington

Anybody looking for a Winston-Salem house rental near the Old Salem district south of Downtown will find themselves in good company. At the Salem Tavern turned museum on South Main Street, you can see where George Washington spent two nights in 1791.

Wander Through Old Salem

Other landmarks in the historic district of Old Salem include the old Winkler Bakery, Single Brother’s House, T. Bagge Merchant Store, and the old Moravian Book Shop, while the Old Salem Museum & Gardens sheds light on life in the town during the 18th century.

Uncover Salem’s Colonial Past

The Museum of Reynolda House in Oak Crest, a short drive northwest of the city center, is another important historical site. It houses a colonial and contemporary art museum, as well as the renowned Reynolda Gardens at Wake Forest on the grounds of the former estate. Those really keen on delving into Winston-Salem’s 18th-century heritage can continue out to the Historic Bethabara Park, a living museum of a 1753 Moravian village.

Information about vacation rentals in Winston-Salem

🏡 Vacation rentals available 1,133 rentals
🌙 Nightly prices starting at $64
⭐ Popular amenities Pets allowed, Internet and Pool
🐾 Pet friendly homes 411 homes
🏊 Vacation rentals with pools 437 homes

Frequently Asked Questions

What is the price per night for a vacation home in Winston-Salem?

Prices for vacation rentals in Winston-Salem start from $64 per night. Average prices for house rentals are $332 per night. Apartment rentals in Winston-Salem cost $162 per night on average.

How many vacation homes are available to book in Winston-Salem?

Currently there are 1,133 vacation rentals from 9 different providers in Winston-Salem.

What are the most popular amenities for vacation homes in Winston-Salem?

The most popular amenities for vacation rentals in Winston-Salem include accommodations that have: Internet, Pets allowed, and Pool.

How many vacation rentals with a pool are in Winston-Salem?

Winston-Salem has 437 Hotel room and Apartment rental options on offer to book.

Are pets allowed in vacation homes in Winston-Salem?

Absolutely, currently there are 411 vacation rentals in Winston-Salem that allow pets and the average nightly price is $248.

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