Vacation rentals in Winston-Salem

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Top-rated vacation rentals in Winston-Salem

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

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!
Dec. 18 – 25
$146 CAD per night
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)
Sep. 30 – Oct. 7
$253 CAD per night
4.94 out of 5 average rating, 180 reviews
Guest favourite
Guest suite in Winston-Salem
Private, Peaceful, Green Hideaway 6 Minutes to WFU
Just minutes from Wake Forest, we have a completely remodeled this very special place. We have often stood at the huge windows of this ground level space and watched mother deer with their fawns play in the yard. Your home away from home is at the end of an already quiet cul-de-sac so traffic noise is zero. Your suite is completely private with its own ground level entrance. Your kitchen has a full size sink, an induction stove, fridge, with all your cookware, dishes. New bath with tub.
Feb. 22 – Mar. 1
$131 CAD per night
4.99 out of 5 average rating, 208 reviews

Popular amenities for Winston-Salem vacation 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 vacation rentals in Winston-Salem

Guest favourite
Cabin in Ardmore
Log Cabin in the city w/brewery tour and tasting
Sep. 11 – 16
$180 CAD per night
4.9 out of 5 average rating, 763 reviews
Guest favourite
Bungalow in Ardmore
Cozy Ardmore Bungalow
Apr. 5 – 12
$245 CAD per night
4.97 out of 5 average rating, 349 reviews
Guest favourite
Guesthouse in Germanton
Mel’s country cottage. Country life near the city.
Apr. 30 – May 7
$111 CAD per night
4.96 out of 5 average rating, 396 reviews
Guest favourite
Home in Ardmore
Camel City Cottage - located near the hospitals
Aug. 5 – 12
$149 CAD per night
4.98 out of 5 average rating, 401 reviews
Guest favourite
Home in Winston-Salem
Salem Twin Deck
Jun. 3 – 10
$212 CAD per night
4.99 out of 5 average rating, 155 reviews
Guest favourite
Condo in Winston-Salem
Old Salem Getaway - Visit DTWS via the Strollway
Apr. 1 – 8
$182 CAD per night
4.97 out of 5 average rating, 113 reviews
Guest favourite
Home in Winston-Salem
Camilas House
Jan. 6 – 13
$167 CAD per night
4.83 out of 5 average rating, 84 reviews
Guest favourite
Guest suite in Winston-Salem
Cozy Konnoak Studio
Aug. 9 – 16
$95 CAD per night
5.0 out of 5 average rating, 37 reviews
Guest favourite
Guest suite in Winston-Salem
Private guest suite @ Maple Leaf Farm
Jan. 4 – 11
$177 CAD per night
5.0 out of 5 average rating, 31 reviews
Guest favourite
Apartment in Winston-Salem
K-Obscura, Romantic Downtown loft
Apr. 22 – 29
$212 CAD per night
4.97 out of 5 average rating, 31 reviews
Guest favourite
Home in Winston-Salem
1 Bed Entire Place Ardmore 3 min Baptist Hospital
Mar. 26 – Apr. 2
$160 CAD per night
4.98 out of 5 average rating, 53 reviews
Guest favourite
Apartment in Winston-Salem
Feelin' Peachy in Downtown WS! Renovated | Queen
Dec. 12 – 19
$178 CAD per night
4.93 out of 5 average rating, 44 reviews

Quick stats about vacation 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