Winston-Salem vacation rentals

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Best Winston-Salem vacation rentals

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$53 - $247$247 - $441$441 - $635$635 - $829$829+ per night

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Free cancellationFree breakfastFree parkingFree internet

Most recommended vacation rentals in Winston-Salem

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3 Mi to Dtwn Winston-Salem Studio on Miller Park! - Winston-Salem - Building
3 Mi to Dtwn Winston-Salem Studio on Miller Park!
Winston-Salem, NC
9.6Wonderful(20)
Apartment
Free Wi-Fi
Pet friendly
$145+
Check availability
Entire condo in downtown winston - Winston-Salem - Patio
Entire condo in downtown winston
Downtown
8.5Very good(32)
Condo
Parking
Free Wi-Fi
$213+
Check availability
2 minutes from Old Salem Meseums - Winston-Salem - Building
2 minutes from Old Salem Meseums
Winston-Salem, NC
House
Free Wi-Fi
$212+
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Guest suite in Winston Salem - Winston-Salem - Living room
Guest suite in Winston Salem
Winston-Salem, NC
9.2Wonderful(74)
Apartment
Free Wi-Fi
$85+
Check availability
1930’s Guest Cottage and Vintage Shop with 1/2 Bath and Full Bed - Winston-Salem - Patio
1930’s Guest Cottage and Vintage Shop with 1/2 Bath and Full Bed
Winston-Salem, NC
9.0Wonderful(2)
Cottage
$75+
Check availability
Winston-Salem Vacation Rental - Walk Downtown! - Winston-Salem - Kitchen
Winston-Salem Vacation Rental - Walk Downtown!
Downtown
10Wonderful(3)
Apartment
Free Wi-Fi
$216+
Check availability
Captains Quarters - Historical Home Downtown Rental - Winston-Salem - Patio
Captains Quarters - Historical Home Downtown Rental
Downtown
9.7Wonderful(25)
Apartment
$131+
Check availability
Backyard camping tent - Winston-Salem - Patio
Backyard camping tent
Winston-Salem, NC
Caravan Park
$84+
Check availability
La Casita: A Cozy Retreat Near Wake Forest University' - Winston-Salem - Kitchen
La Casita: A Cozy Retreat Near Wake Forest University'
Winston-Salem, NC
9.5Wonderful(47)
House
Free Wi-Fi
$200+
Check availability
Renovated 1br Apartment Steps From Wfu Hospital - Winston-Salem - Bedroom
Renovated 1br Apartment Steps From Wfu Hospital
Winston-Salem, NC
10Wonderful(3)
Apartment
Free Wi-Fi
$71+
Check availability
Modern guest apartment in perfect location! - Winston-Salem - Bedroom
Modern guest apartment in perfect location!
Winston-Salem, NC
9.2Wonderful(10)
Apartment
Free Wi-Fi
$144+
Check availability
Quiet Suburban House in Winston Salem - Winston-Salem - Building
Quiet Suburban House in Winston Salem
Winston-Salem, NC
House
$62+
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Charming Condo Near Wfu And Hospitals, Full Kitchen, Strong Wifi, In-Unit Laundry - Winston-Salem
Charming Condo Near Wfu And Hospitals, Full Kitchen, Strong Wifi, In-Unit Laundry
Winston-Salem, NC
10Wonderful(3)
Apartment
Parking
Free Wi-Fi
$218+
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Sapphire Shire - Winston-Salem
Sapphire Shire
Winston-Salem, NC
10Wonderful(8)
House
Parking
Free Wi-Fi
$228+
Check availability
Downtown Winston-Salem Condo with Private Library! - Winston-Salem
Downtown Winston-Salem Condo with Private Library!
Winston-Salem, NC
9.4Wonderful(13)
Apartment
Free Wi-Fi
$239+
Check availability
Classy Catch - Winston-Salem
Classy Catch
Winston-Salem, NC
9.5Wonderful(17)
House
Parking
Free Wi-Fi
$216+
Check availability
Booking Insights

KAYAK’s insights for vacation rentals in Winston-Salem

Discover seasonal trends, ideal booking windows, and other data-driven tips to plan your stay in Winston-Salem with confidence.

What is the cheapest day of the week to book a vacation rental in Winston-Salem?

Thursday offers the lowest rates in Winston-Salem, with an average nightly price of $77. The highest prices are found on Sunday, with average rates at $337.

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Good to know

Low season

High season

Average price (weeknight)

Average price (weekend night)

December
November
$182
$141
Cheapest month to stay with an average 56% drop in price.
Most expensive month to stay with an average 117% rise in price.
Average Sun - Thu price over the last 2 weeks.
Average Fri & Sat price over the last 2 weeks.

KAYAK's top tips for finding Winston-Salem vacation rental deals

  • Hot tub, pet friendly, and pool are the most popular vacation rental property amenities in Winston-Salem
  • Vacation rentals in Winston-Salem are around 51% more expensive than hotels on average. Search here to compare prices for all accommodation types in Winston-Salem.
  • The best vacation rental properties in Winston-Salem are Captains Quarters - Historical Home Downtown Rental (9.7, 25 reviews), 3 Mi to Dtwn Winston-Salem Studio on Miller Park! (9.6, 20), and Private & sweet patio level apartment in downtown Winston-Salem (9.6, 80), based on ratings and reviews from real travelers.
  • Downtown is the neighborhood in Winston-Salem with the most affordable vacation rental properties (11 properties with an average price of $193 per night). Entire condo in downtown winston, Winston-Salem Vacation Rental - Walk Downtown!, and Captains Quarters - Historical Home Downtown Rental are the most popular rental properties in Downtown.
  • If you’re looking for a cheap vacation rental in Winston-Salem, you should consider visiting during the low season. The cheapest vacation homes in Winston-Salem can be found in December and September.
  • The cheapest night for renting a vacation home in Winston-Salem is Thursday. In contrast, the most expensive is Sunday.
  • Vacation rentals are a popular choice for both long and short-term stays. KAYAK users usually book their vacation rental in Winston-Salem for 7 days.

FAQs when booking a vacation home in Winston-Salem

  • How much is a vacation rental for a week in Winston-Salem?

    The average price for a weekly Winston-Salem vacation rental found by KAYAK users in the last 2 weeks is $745.

  • How much is a vacation rental for a month in Winston-Salem?

    The average price for a monthly Winston-Salem vacation rental found by KAYAK users in the last 2 weeks is $3,191.

  • What types of vacation rentals are available in Winston-Salem?

    There are loads of different property types that you can make your vacation home in Winston-Salem. You’ll find apartments, bungalows, cabins, caravans, caravan parks, condos, cottages, houses, homestays and villas.

  • What are some of the most-loved vacation rentals available in Winston-Salem?

    If you’re looking for something special, the vacation rental most loved by KAYAK users is Guest suite in Winston Salem.

  • Are there any pet-friendly vacation rentals in Winston-Salem?

    There are a number of dog and pet-friendly Winston-Salem vacation rentals, with around 5% allowing you to bring your pet along with you.

  • How much is a vacation rental in Winston-Salem for tonight?

    In the last 72 hours, users have found Winston-Salem vacation rentals for tonight for as low as $271. Search here for similar prices

  • How can I find vacation rentals near me in Winston-Salem?

    Take a look at our vacation rentals map to find the best vacation rental homes near you.

Where to stay in Winston-Salem?

Our map will help you find the perfect place to stay in Winston-Salem by showing you the exact location of each vacation rental.

Everything you need to know for your stay in Winston-Salem