Holiday 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

Guest suite in Pfafftown

4.97 out of 5 average rating, 124 reviews

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!

12–19 Dec

£85 per night
Guest favourite

Home in Winston-Salem

4.94 out of 5 average rating, 182 reviews

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)

20–27 Nov

£151 per night
Guest favourite

Guest suite in Winston-Salem

4.99 out of 5 average rating, 501 reviews

The Man Cave

The Man Cave is close to the highway. It is minutes away from downtown Winston-Salem, Wake Forest University, Hanes Mall, and Baptist Hospital. You'll love the place because of its private entrance and great "Man Cave" amenities... King bed, wi-fi, pool table, dartboard, 50" TV & DirecTV satellite cable, Keurig machine, full kitchen, washer/dryer, etc. Don't let the name fool you... It is good for a couples get away, solo adventurers, and business travelers looking for a unique experience.

17–24 Sept

£119 per night

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
Novant Health Forsyth Medical Center7 locals recommend
Old Salem Museums & Gardens Administrative Offices36 locals recommend
Winston Salem Fairgrounds Annex3 locals recommend

Other great holiday rentals in Winston-Salem

Guest favourite

Guest suite in Winston-Salem

4.98 out of 5 average rating, 247 reviews

Ardmore studio, close to downtown, hospitals & WFU

19–26 Aug

£91 per night
Guest favourite

Home in Ardmore

4.98 out of 5 average rating, 403 reviews

Camel City Cottage - located near the hospitals

3–10 Sept

£87 per night
Guest favourite

Apartment in Winston-Salem

4.9 out of 5 average rating, 245 reviews

Charming quiet condo all to yourself

1–8 Mar

£54 per night
Guest favourite

Apartment in Winston-Salem

4.97 out of 5 average rating, 114 reviews

Old Salem Getaway - Visit DTWS via the Strollway

20–27 Jun

£113 per night
Guest favourite

Home in Winston-Salem

4.9 out of 5 average rating, 185 reviews

House in Sunnyside W-S w/Brewery Tour and Tasting!

31 Dec – 7 Jan

£111 per night
Guest favourite

Home in Winston-Salem

4.99 out of 5 average rating, 155 reviews

Salem Twin Deck

24–31 Aug

£133 per night
Guest favourite

Townhouse in Winston-Salem

5.0 out of 5 average rating, 13 reviews

Spacious Townhouse Close to Everything

28 Apr – 5 May

£81 per night
Guest favourite

Home in Winston-Salem

4.84 out of 5 average rating, 85 reviews

Camilas House

28 Feb – 7 Mar

£101 per night
Guest favourite

Guest suite in Winston-Salem

5.0 out of 5 average rating, 37 reviews

Cozy Konnoak Studio

15–22 Jan

£56 per night
Guest favourite

Guest suite in Winston-Salem

4.97 out of 5 average rating, 59 reviews

Bright and refreshing studio apartment in Ardmore

5–12 Jun

£89 per night
Guest favourite

Flat in Winston-Salem

5.0 out of 5 average rating, 38 reviews

The Foothills in Downtown WS! Renovated | King Bed

12–19 Mar

£117 per night
Guest favourite

Flat in Winston-Salem

4.97 out of 5 average rating, 33 reviews

K-Obscura, Romantic Downtown loft

6–13 Jun

£125 per night

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