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Winston-Salem vacation rentals

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Best Winston-Salem vacation rentals

Most recommended vacation rentals in Winston-Salem

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Charming Winston-Salem Studio on Miller Park! - Winston-Salem - Building
Charming Winston-Salem Studio on Miller Park!
Winston-Salem, NC
9.2Wonderful(8)
Free Wi-Fi
Pet friendly
$160+
Check availability
Entire condo in downtown winston - Winston-Salem - Patio
Entire condo in downtown winston
Downtown
8.8Very good(23)
Parking
Free Wi-Fi
$212+
Check availability
Winston-Salem Vacation Rental - Walk Downtown! - Winston-Salem - Kitchen
Winston-Salem Vacation Rental - Walk Downtown!
Downtown
Free Wi-Fi
$239+
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Cozy Guest Suite In Winston Salem - Winston-Salem - Living room
Cozy Guest Suite In Winston Salem
Winston-Salem, NC
Free Wi-Fi
$79+
Check availability
2 minutes from Old Salem Meseums - Winston-Salem - Dining room
2 minutes from Old Salem Meseums
Winston-Salem, NC
Free Wi-Fi
$212+
Check availability
Three bedroom 5 minutes to state university & town, 10 min to baptist hospital - Winston-Salem - Living room
Three bedroom 5 minutes to state university & town, 10 min to baptist hospital
Winston-Salem, NC
9.1Wonderful(14)
Free Wi-Fi
$164+
Check availability
Captains Quarters - Historical Home Downtown Rental - Winston-Salem - Patio
Captains Quarters - Historical Home Downtown Rental
Downtown
$130+
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Cozy Winston-Salem Home Less Than 2 Mi to Downtown! - Winston-Salem - Living room
Cozy Winston-Salem Home Less Than 2 Mi to Downtown!
Winston-Salem, NC
Free Wi-Fi
$773+
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Sapphire Shire - Winston-Salem - Bedroom
Sapphire Shire
Winston-Salem, NC
10Wonderful(4)
Parking
Free Wi-Fi
$238+
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Private & sweet patio level apartment in downtown Winston-Salem - Winston-Salem - Living room
Private & sweet patio level apartment in downtown Winston-Salem
Downtown
$217+
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Quiet Suburban House in Winston Salem - Winston-Salem - Building
Quiet Suburban House in Winston Salem
Winston-Salem, NC
$62+
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La Casita: A Cozy Retreat Near Wake Forest University\' - Winston-Salem - Kitchen
La Casita: A Cozy Retreat Near Wake Forest University\'
Winston-Salem, NC
9.6Wonderful(37)
Free Wi-Fi
$251+
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Heated Pool l Indoor Jacuzzi Tubs I Arcade l Outdoor Hot Tub - Winston-Salem - Living room
Heated Pool l Indoor Jacuzzi Tubs I Arcade l Outdoor Hot Tub
Winston-Salem, NC
Parking
Free Wi-Fi
Pool
Pet friendly
$547+
Check availability
Backyard camping tent - Winston-Salem - Patio
Backyard camping tent
Winston-Salem, NC
$88+
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Ardmore Home - Winston-Salem
Ardmore Home
Winston-Salem, NC
Pet friendly
$160+
Check availability
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)
Parking
Free Wi-Fi
$267+
Check availability

Vacation rentals near M.C. Benton Jr. Convention Center

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Cozy Guest Suite In Winston Salem - Winston-Salem - Living room
Cozy Guest Suite In Winston Salem
Winston-Salem, NC
Free Wi-Fi
$79+
Check availability
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$37 - $210$210 - $383$383 - $556$556 - $729$729+ per night

Property Types

ApartmentCondoCottageHomestayHouse

Search by freebies

Free cancellationFree breakfastFree parkingFree internet

Good to know

Low season

May

High season

September

Average price (weeknight)

$197

Average price (weekend night)

$142
Cheapest month to stay with an average 53% drop in price.
Most expensive month to stay with an average 235% 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 48% 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 Deacon Stays: The Brookwood - Walk To Wfu (9.9, 23 reviews), Elegant 2bed1b Condo In Quiet Neighborhood Near Wfu, Unsa, Hospitals. (9.8, 21), and Renovated Perfection in Quiet W-S Neighborhood (9.8, 61), based on ratings and reviews from real travelers.
  • Downtown is the neighborhood in Winston-Salem with the most affordable vacation rental properties (21 properties with an average price of $147 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.
  • Vacation rentals are a popular choice for both long and short-term stays. KAYAK users usually book their vacation rental in Winston-Salem for 9 days.
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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 $1,547.

  • 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 $6,630.

  • 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, 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 Cozy 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 19% 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 $58. Search here for similar prices

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

    In the last 72 hours, users have found Winston-Salem vacation rentals for this weekend for as low as $254 per night. 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.

See more FAQs

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

Winston-Salem vacation rental deals. Search for vacation homes, apartments, condos, cabins, cottages, villas and more in Winston-Salem. Find cheap vacation homes to rent in Winston-Salem. KAYAK searches hundreds of travel sites to help you find and book a vacation rental in Winston-Salem that suits you best.

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