Winston-Salem vacation rentals

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Best Winston-Salem vacation rentals

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6+ Okay7+ Good8+ Great9+ Excellent

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$62 - $224$224 - $386$386 - $548$548 - $710$710+ per night

Property Types

ApartmentCondoCottageHomestayHouse

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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
9.2Wonderful(10)
Free Wi-Fi
Pet friendly
$152+
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Entire condo in downtown winston - Winston-Salem - Patio
Entire condo in downtown winston
Downtown
8.8Very good(27)
Parking
Free Wi-Fi
$197+
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Winston-Salem Vacation Rental - Walk Downtown! - Winston-Salem - Kitchen
Winston-Salem Vacation Rental - Walk Downtown!
Downtown
Free Wi-Fi
$239+
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2 minutes from Old Salem Meseums - Winston-Salem - Dining room
2 minutes from Old Salem Meseums
Winston-Salem, NC
Free Wi-Fi
$217+
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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+
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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
$214+
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Captains Quarters - Historical Home Downtown Rental - Winston-Salem - Patio
Captains Quarters - Historical Home Downtown Rental
Downtown
$129+
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Sapphire Shire - Winston-Salem - Bedroom
Sapphire Shire
Winston-Salem, NC
10Wonderful(4)
Parking
Free Wi-Fi
$195+
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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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The Frequent Flyer - Winston-Salem - Living room
The Frequent Flyer
Downtown
9.5Wonderful(6)
Parking
Free Wi-Fi
Pet friendly
$233+
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Backyard camping tent - Winston-Salem - Patio
Backyard camping tent
Winston-Salem, NC
$84+
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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
$102+
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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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Charming Apartment in Downtown Winston-Salem! - Winston-Salem - Living room
Charming Apartment in Downtown Winston-Salem!
Downtown
7.0Good(1)
Free Wi-Fi
$256+
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Ardmore Home - Winston-Salem
Ardmore Home
Winston-Salem, NC
Pet friendly
$160+
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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)
Parking
Free Wi-Fi
$295+
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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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Good to know

Low season

High season

Average price (weeknight)

Average price (weekend night)

May
September
$176
$166
Cheapest month to stay with an average 40% drop in price.
Most expensive month to stay with an average 136% 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 63% 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 La Casita: A Cozy Retreat Near Wake Forest University\' (9.6, 37 reviews), Entire condo in downtown winston (8.8, 27) and Entire condo in downtown winston (8.8, 27), 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 $216 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 May and December.
  • The cheapest night for renting a vacation home in Winston-Salem is Saturday. In contrast, the most expensive is Thursday.
  • Vacation rentals are a popular choice for both long and short-term stays. KAYAK users usually book their vacation rental in Winston-Salem for 10 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 $402.

  • 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 $1,725.

  • 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 15% 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 $227. 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 $158 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.

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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