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
The Zen Ranch - Modern Luxury with Relaxing Vibes
1960s ranch style home on 2 acres with 2,400ft² interior. This home has been fully remodeled with a large open floor plan and all modern amenities and decor. With ample yard and patio space, large bedrooms, bonus room and 3 full bathrooms there is plenty of space to spread out. • Abundant Natural Lighting • Backyard w/ patio + fire pit + hammocks • Comfy Beds • Fully stocked Chefs Kitchen • Large Private Deck + BBQ grill • Indoor fireplace • 400Mps WiFi • 3 x 4K TVs w/ Disney, Netflix & Prime
7 – 14 Jan
4.99 out of 5 average rating, 115 reviews
Guest favourite
Guest suite in Pfafftown
The Colonial Winston-Salem: a boutique guest suite
A beautifully decorated basement suite 15 minutes from downtown Winston, near Lewisville and some of the best wineries! The space is entirely yours, complete with a charming patio, kitchenette, full bathroom, and studio bedroom/living room. Sit out on the patio with a cup of coffee from our fully stocked coffee bar and watch the deer & birds, or grab a book and snuggle in cozy bedding. We are an active family with dogs & kids living upstairs, so we've provided everything you need for quiet!
29 Aug – 5 Sept
4.97 out of 5 average rating, 124 reviews
Guest favourite
Home in Winston-Salem
Cozy King Blue H2O Staycation , Pool & Hot Tub
Quiet secluded STAYCATION w/ Fully Fenced Back Yard for the PUPS. We have a hot tub for year round use and a Stock Tank Pool . A fire pit to unwind. Double Hammock & Enjoy a back yard BBQ with a built in bar top table and a cozy Sectional to enjoy the outdoors. Inside we have an amazing plush King size mattress to take all stress away. Full kitchen * Hot tub - I will do my best to have it available at all times unless there is a mechanical issue. (No refunds if hot tub is not available)
30 Sept – 7 Oct
4.94 out of 5 average rating, 180 reviews

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
Novant Health Forsyth Medical Center7 locals recommend
Winston Salem Fairgrounds Annex3 locals recommend

Other great holiday rentals in Winston-Salem

Guest favourite
Guest suite in Winston-Salem
Comfortable and Convenient Studio
24 June – 1 July
4.98 out of 5 average rating, 111 reviews
Guest favourite
Condo in Winston-Salem
Sanctuary – 1bedroom & 1bathroom
3 – 10 Aug
4.9 out of 5 average rating, 374 reviews
Guest favourite
Tiny home in Winston-Salem
Roost20 @ The Tiny House Farm
1 – 8 Aug
4.87 out of 5 average rating, 246 reviews
Guest favourite
Guest suite in Winston-Salem
Entire Guest Suite near Wake, Reynolda House
14 – 21 Feb
4.88 out of 5 average rating, 168 reviews
Guest favourite
Bungalow in Winston-Salem
Cozy Ardmore Bungalow
5 – 12 Apr
4.97 out of 5 average rating, 349 reviews
Guest favourite
Condo in Winston-Salem
Charming quiet condo all to yourself
23 – 30 May
4.9 out of 5 average rating, 245 reviews
Guest favourite
Home in Winston-Salem
Camilas House
17 – 24 Sept
4.83 out of 5 average rating, 84 reviews
Guest favourite
Guesthouse in Kernersville
The Bungalow at Weather Ridge
29 June – 6 July
5.0 out of 5 average rating, 71 reviews
Guest favourite
Guest suite in Winston-Salem
Private guest suite @ Maple Leaf Farm
6 – 13 Sept
5.0 out of 5 average rating, 31 reviews
Guest favourite
Home in Winston-Salem
CHARMING WEST SALEM BUNGALOW
4 – 11 Sept
4.97 out of 5 average rating, 88 reviews
Guest favourite
Apartment in Winston-Salem
Renovated King | Walk Downtown & Baptist Hospital!
25 Apr – 2 May
5.0 out of 5 average rating, 37 reviews
Guest favourite
Apartment in Winston-Salem
Charming Historic West End Apt C, main level
20 – 27 June
4.93 out of 5 average rating, 28 reviews

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