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Vacation rentals in Winston-Salem

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Top-rated holiday rentals in Winston-Salem

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favourite
Home in Winston-Salem
House in Sunnyside W-S w/Brewery Tour and Tasting!
Absolutely NO Parties or large gatherings allowed. You will be kicked out. Only guest registered are allowed to stay. You and your family will enjoy this spacious 3 bedroom home which is located in the historic Sunnyside area of town! Located a little over 1 mile into the downtown area, you will have easy access to nightlife, tourist attractions and lots of great food options! If you are a beer fan, I own Hoots Beer Co. and offer a free tour and tasting with your stay, so just ask!
25 Jan – 1 Feb
Guest favourite
Guesthouse in Germanton
Mel’s country cottage. Country life near the city.
Private detached effeciency apartment in a country setting near WinstonSalem. Queen bed, kitchenette with sink and essentials, sofa, smart TV, full bath, covered porch. Relax by the creek or enjoy nature walks. Watch the occasional deer & other wildlife. Use the grill or fire pit at your leisure. Pets welcome. Local restaurant & convenient store 1 min. away. Close to many tourist destinations- Hanging Rock, Winston Salem, Pilot Mt. Belews Creek power station.
12 – 19 Dec
Guest favourite
Condo in Winston-Salem
Charming quiet condo all to yourself
This is a cozy non pet condo for two. Perfect for extended stay hospital visits. Next door to Novant Health care and 1.5 miles from Baptist Hospital. Grocery and restaurants in walking distance. Will meet new guests in person. A few easy steps to the lower level then flat up to the door. Non-smoking. No pets. Contact host in message box for availability.
28 June – 5 July

Popular amenities for Winston-Salem holiday rentals

Stay near Winston-Salem's top sights

Hanes Mall57 locals recommend
Lawrence Joel Veterans Memorial Coliseum13 locals recommend
Benton Convention Center8 locals recommend
Old Salem Museums & Gardens Administrative Offices36 locals recommend
Walmart Supercenter30 locals recommend
Novant Health Forsyth Medical Center7 locals recommend

Other great holiday rentals in Winston-Salem

Guest favourite
Cabin in Winston-Salem
The Blue Door Cabin
1 – 8 Apr
Guest favourite
Apartment in Winston-Salem
Bright & Cozy Upstairs Apartment/Near Downtown
3 – 10 May
Guest favourite
Home in Winston-Salem
Cozy King Blue H2O Staycation , Pool & Hot Tub
11 – 18 Oct
Guest favourite
Guest suite in Winston-Salem
Buena Vista In-laws suite
3 – 10 Oct
Guest favourite
Home in Winston-Salem
The Zen Ranch - Modern Luxury with Relaxing Vibes
23 – 30 Mar
Guest favourite
Guest suite in Winston-Salem
The Man Cave
7 – 14 Sept
Guest favourite
Condo in Winston-Salem
Modern Corner Condo near Old Salem,Downtown,UNCSA
12 – 19 Mar
Guest favourite
Guest suite in Winston-Salem
Ardmore studio, close to downtown, hospitals & WFU
3 – 10 June
Guest favourite
Guest suite in Winston-Salem
Private, Peaceful, Green Hideaway 6 Minutes to WFU
20 – 27 Sept
Guest favourite
Apartment in Winston-Salem
🌹Rose Room Apartment, West Salem Art Hotel
26 Apr – 3 May
Guest favourite
Condo in Winston-Salem
Sanctuary – 1bedroom & 1bathroom
19 – 26 July
Guest favourite
Apartment in Winston-Salem
Urban oasis in downtown W-S; sparkling clean
21 – 28 Feb

Quick stats about holiday rentals in Winston-Salem

Total rentals

950 properties

Rentals with dedicated workspaces

600 properties have a dedicated workspace

Rentals with a pool

50 properties have a pool

Pet-friendly rentals

370 properties allow pets

Family-friendly rentals

490 properties are a good fit for families

Total number of reviews

38K reviews

Destinations to explore