Holiday rentals in Winston-Salem

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Top-rated holiday rentals in Winston-Salem

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Guest favourite

Guest suite in Pfafftown

4.97 out of 5 average rating, 129 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!

23–30 Mar

$121 SGD per night

Guest favourite

Home in Winston-Salem

4.99 out of 5 average rating, 159 reviews

Salem Twin Deck

Conveniently located in downtown Winston-Salem, this well-maintained cottage built in 1900 includes a recently updated kitchen with island, wood floors, dining room, living room with full futon, washer/dryer, bedroom with queen, beautiful bathroom and walk-in shower. Easy walking distance to downtown restaurants, short drive to WFU main campus, Med School, WSSU and UNCSA. One off-street parking spot available. Self check-in only, but we live next door if you need anything or have questions.

25 May – 1 Jun

$180 SGD per night

Guest favourite

Guest suite in Winston-Salem

4.99 out of 5 average rating, 508 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.

18–25 Sep

$195 SGD per night

Guest favourite

Guest suite in Winston-Salem

4.99 out of 5 average rating, 210 reviews

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.

18–25 Oct

$108 SGD per night

Guest favourite

Flat in Winston-Salem

5.0 out of 5 average rating, 245 reviews

Bright & Cozy Upstairs Apartment/Near Downtown

Sunny one-bedroom apartment on 2nd floor of historic home. Close to downtown & WFU/Baptist Hospital. You'll have the whole place to yourself, with a private entrance and coded deadbolt for keyless entry. Open living area with full-sized futon. Kitchen equipped with stove, oven, full-sized fridge & microwave. Coffee, tea, and snacks provided. Separate bedroom with queen-sized bed. Bathroom with full-sized shower/tub and washer/dryer. Off-street parking available. Welcome home!

28 Aug – 4 Sep

$118 SGD per night

Guest favourite

Guest suite in Winston-Salem

4.98 out of 5 average rating, 254 reviews

Ardmore studio, close to downtown, hospitals & WFU

This unique studio space is located in the historic Ardmore district conveniently located minutes from both Forsyth and Baptist hospitals, downtown and WFU. It is also a short stroll to Ardmore coffee shop, Carlisles pub, Arthur’s diner, famous PB’s hot dogs and burgers, groceries and other conveniences! Private entrance with keyless entry, street parking and 1 guest space on grounds. Queen bed & fold down couch. Fridge/freezer, microwave, toaster/toaster oven, coffee pot, kettle

30 Mar – 6 Apr

$119 SGD per night

Guest favourite

Apartment in Winston-Salem

4.97 out of 5 average rating, 118 reviews

Old Salem Getaway - Visit DTWS via the Strollway

We love our comfy third floor condo with elevator access. Whether you are in town for business or pleasure, this condo fits the bill. Walk to Old Salem, UNCSA, and Salem College. Jog or bike Salem Creek trail, which is at our doorstep. Stroll through Old Salem on your way to downtown’s amazing eateries and breweries. Close by are Wake Forest University, WSSU and downtown Winston-Salem, and hospitals - this condo is central to anywhere in the Winston-Salem area.

25 May – 1 Jun

$152 SGD per night

Guest favourite

Guest house in Germanton

4.96 out of 5 average rating, 407 reviews

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.

18–25 Oct

$111 SGD per night

Guest favourite

Apartment in Winston-Salem

4.91 out of 5 average rating, 148 reviews

Open Stylish Condo near Old Salem, Downtown, UNCSA

Overlooking historic Old Salem, this spacious 3rd floor condominium offers modern amenities and unique charm. Conveniently located in walking distance to downtown, Salem College, and UNCSA, and just a short drive to WSSU and Wake Forest. Perfect for families, faculties, or college tours. Secure building with elevator access and free parking. You'll love this bright open space, with high ceilings, a full and spacious kitchen, and your own breakfast balcony.

5–12 May

$125 SGD per night

Guest favourite

Home in Ardmore

4.98 out of 5 average rating, 408 reviews

Camel City Cottage - located near the hospitals

Our *non-smoking* home is located in the desirable Ardmore residential area of Winston-Salem...quiet yet still close to many restaurants and shopping. This cottage has all the modern amenities while still retaining it's 1940's cottage charm. The kitchen has been completely remodeled and has all the appliances you would need. The living room and each bedroom have a TV with an antennae and access to your streaming services such as Roku, Prime, and Sling.

5–12 Oct

$124 SGD per night

Guest favourite

Apartment in Winston-Salem

4.95 out of 5 average rating, 353 reviews

A Bright Spot in West End

Welcome to the Shenandoah house condominiums! Located in the historic West End neighborhood of downtown Winston-Salem. Spacious one bedroom with lots of natural light, hardwood floors, eat in kitchen and private screened porch. Filled with works from many of Winston's local artists. Fully equipped for your stay. Easy walking distance to restaurants, bars, shopping, entertainment, breweries, parks and public transportation. Free parking!

10–17 May

$112 SGD per night

Guest favourite

Guest suite in Winston-Salem

4.99 out of 5 average rating, 167 reviews

Buena Vista In-laws suite

Newly refreshed second-story In-Laws suite above a detached garage. The suite includes hardwood floors, full kitchen, king bed, and a separate living room area. Located on a gated 1/2 acre property on the edge of Winston's highly desirable Buena Vista neighborhood. Guests can use courtyard area for eating, working or talking.

20–27 Jan

$181 SGD per night