Winston-Salem vacation rentals

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Best Winston-Salem vacation rentals

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$59 - $252$252 - $444$444 - $637$637 - $829$829+ per night

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Most recommended vacation rentals in Winston-Salem

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Entire condo in downtown winston - Winston-Salem - Patio
Entire condo in downtown winston
Downtown
8.5Very good(32)
Parking
Free Wi-Fi
$219+
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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)
Free Wi-Fi
Pet friendly
$167+
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Winston-Salem Vacation Rental - Walk Downtown! - Winston-Salem - Kitchen
Winston-Salem Vacation Rental - Walk Downtown!
Downtown
10Wonderful(3)
Free Wi-Fi
$326+
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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
$212+
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Guest suite in Winston Salem - Winston-Salem - Living room
Guest suite in Winston Salem
Winston-Salem, NC
9.2Wonderful(73)
Free Wi-Fi
$84+
Check availability
Captains Quarters - Historical Home Downtown Rental - Winston-Salem - Patio
Captains Quarters - Historical Home Downtown Rental
Downtown
9.7Wonderful(25)
$133+
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Backyard camping tent - Winston-Salem - Patio
Backyard camping tent
Winston-Salem, NC
$85+
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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
8.0Very good(1)
$82+
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The Frequent Flyer - Winston-Salem - Living room
The Frequent Flyer
Downtown
9.9Wonderful(14)
Parking
Free Wi-Fi
$222+
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Charming Apartment in Downtown Winston-Salem! - Winston-Salem - Living room
Charming Apartment in Downtown Winston-Salem!
Downtown
9.3Wonderful(4)
Free Wi-Fi
$228+
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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
9.5Wonderful(45)
Free Wi-Fi
$218+
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Renovated 1br Apartment Steps From Wfu Hospital - Winston-Salem - Bedroom
Renovated 1br Apartment Steps From Wfu Hospital
Winston-Salem, NC
10Wonderful(3)
Free Wi-Fi
$136+
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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
$279+
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Sapphire Shire - Winston-Salem
Sapphire Shire
Winston-Salem, NC
10Wonderful(8)
Parking
Free Wi-Fi
$261+
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Winston-Salem Condo with Balcony Steps to Golf! - Winston-Salem
Winston-Salem Condo with Balcony Steps to Golf!
Winston-Salem, NC
8.7Very good(6)
Free Wi-Fi
$369+
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Downtown Winston-Salem Condo with Private Library! - Winston-Salem
Downtown Winston-Salem Condo with Private Library!
Winston-Salem, NC
9.4Wonderful(13)
Free Wi-Fi
$310+
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Vacation rentals near M.C. Benton Jr. Convention Center

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Guest suite in Winston Salem - Winston-Salem - Living room
Guest suite in Winston Salem
1.8 mi from M.C. Benton Jr. Convention Center, Winston-Salem, United States
9.2Wonderful(73)
Free Wi-Fi
$84+
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?

Friday offers the lowest rates in Winston-Salem, with an average nightly price of $104. The highest prices are found on Thursday, with average rates at $187.
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Good to know

Low season

High season

Average price (weeknight)

Average price (weekend night)

November
December
$170
$107
Cheapest month to stay with an average 44% drop in price.
Most expensive month to stay with an average 108% 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 52% 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 Renovated Perfection in Quiet W-S Neighborhood (9.8, 80 reviews), An urban oasis in downtown Winston-Salem (9.7, 39), and Captains Quarters - Historical Home Downtown Rental (9.7, 25), 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 $214 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 November and September.
  • The cheapest night for renting a vacation home in Winston-Salem is Friday. 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 12 days.

FAQs when booking a vacation home in Winston-Salem

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

    The average price for a monthly Winston-Salem Rental rental found by KAYAK users in the last 2 weeks is $1,725.

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

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