Winston-Salem vacation rentals

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Booking Insights
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Best Winston-Salem vacation rentals

These are the best prices for Aug 15 - 16.
Cozy 1-bedroom condo in Downtown Winston-Salem, free parking! - Winston-Salem - Kitchen
Cozy 1-bedroom condo in Downtown Winston-Salem, free parking!
Winston-Salem, NC
9.7Wonderful(8)
Condo
$194+
Check availability
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(22)
Apartment
$176+
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Winston Ardmore Executive King Bed Suite - Winston-Salem - Dining room
Winston Ardmore Executive King Bed Suite
Winston-Salem, NC
House
$170+
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Guest suite in Winston Salem - Winston-Salem - Living room
Guest suite in Winston Salem
Winston-Salem, NC
9.1Wonderful(83)
Apartment
$94+
Check availability
Charming 4bed/3bath with Pool Table -2King/3Queen Beds - Winston-Salem - Kitchen
Charming 4bed/3bath with Pool Table -2King/3Queen Beds
Winston-Salem, NC
10Wonderful(2)
House
$321+
Check availability
Winston-Salem Vacation Rental - Walk Downtown! - Winston-Salem - Kitchen
Winston-Salem Vacation Rental - Walk Downtown!
Downtown
10Wonderful(3)
Apartment
$253+
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Entire condo in downtown winston - Winston-Salem - Patio
Entire condo in downtown winston
Downtown
8.6Very good(35)
Condo
$209+
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Backyard camping tent - Winston-Salem - Patio
Backyard camping tent
Winston-Salem, NC
Caravan Park
$97+
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Classy 1br Steps From Wf Hospital - Free Parking - Winston-Salem - Bedroom
Classy 1br Steps From Wf Hospital - Free Parking
Winston-Salem, NC
9.5Wonderful(4)
Apartment
$185+
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Renovated Perfection in Quiet W-S Neighborhood - Winston-Salem - Dining room
Renovated Perfection in Quiet W-S Neighborhood
Winston-Salem, NC
9.8Wonderful(94)
House
$374+
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Cozy 2-bedroom house in Winston-Salem with AC, WiFi, washer/drier, full kitchen. - Winston-Salem - Building
Cozy 2-bedroom house in Winston-Salem with AC, WiFi, washer/drier, full kitchen.
Winston-Salem, NC
House
$158+
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King Beds Hot Tub Arcade Gas Grill Firep - Winston-Salem - Bedroom
King Beds Hot Tub Arcade Gas Grill Firep
Winston-Salem, NC
House
$426+
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Landing Stylish 1bd Pool Gym - Winston-Salem - Living room
Landing Stylish 1bd Pool Gym
Winston-Salem, NC
Apartment
$168+
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Private Master Queen Room - Winston-Salem
Private Master Queen Room
Winston-Salem, NC
8.3Very good(3)
Homestay
$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
9.8Wonderful(3)
Apartment
$271+
Check availability
Northcliffe 104 I Fully Furnished 1 Bedroom 1bth - Winston-Salem
Northcliffe 104 I Fully Furnished 1 Bedroom 1bth
Winston-Salem, NC
Apartment
$91+
Check availability

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
9.1Wonderful(83)
Apartment
$94+
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.

Which month has the cheapest vacation rental rates in Winston-Salem?

Based on vacation rental prices in Winston-Salem found by KAYAK users over the last 12 months.

Vacation rentals are cheapest in Winston-Salem in July, with average rates of $56. In comparison, November is the most expensive month, with prices at $1,207.

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 Monday, with average rates at $253.

How much is a vacation rental in Winston-Salem for tonight by property type?

Based on vacation rental availability in Winston-Salem in the last 5 days.

The best deal for a vacation rental in Winston-Salem found by KAYAK users in the last 5 days was $106 in a House. Caravan Park prices start at $106.

How much is a vacation rental in Winston-Salem for this weekend by property type?

Based on vacation rental availability in Winston-Salem in the last 5 days.

The best deal for a vacation rental in Winston-Salem found by KAYAK users for the upcoming weekend was $194 in a Apartment. Houses prices start at $282 and Cottages at $602.

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Good to know

Low season

High season

Average price (weeknight)

Average price (weekend night)

July
November
$177
$139
Cheapest month to stay with an average 52% drop in price.
Most expensive month to stay with an average 565% 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 136% cheaper 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 Elegant Pet Friendly Ranch Home Close To Everything! (10.0, 35 reviews), Winston-Salem's Man Cave (9.9, 76), and Renovated Perfection in Quiet W-S Neighborhood (9.8, 94), based on ratings and reviews from real travelers.
  • Downtown is the neighborhood in Winston-Salem with the most affordable vacation rental properties (10 properties with an average price of $197 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 July and February.
  • The cheapest night for renting a vacation home in Winston-Salem is Thursday. In contrast, the most expensive is Monday.
  • 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 $1,224.

  • 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 $5,246.

  • 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, cabins, caravans, caravan parks, condos, cottages, houses, homestays, inns 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 21% 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 $106. 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 $224 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