Holiday houses 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, 151 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!

Guest favourite

Rental unit in Winston-Salem

4.93 out of 5 average rating, 128 reviews

Entire Apartment near Atrium Baptist Hospital

Beautifully remodeled apartment in the West Highlands neighborhood, near Atrium Health Wake Forest Baptist Medical Center and the Bowman Gray Campus at the hospital. We're a short walk from Hanes Park and one mile from downtown. The bright, open apartment has one master bedroom with a king-size bed, and the ensuite bathroom features a clawfoot tub. Spacious living room includes a TV with Disney+ and Netflix. The full kitchen is built around the 48" Wolf gas stove and a large farmhouse sink.

Guest favourite

Guest suite in Winston-Salem

4.98 out of 5 average rating, 227 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.

Guest favourite

Home in Winston-Salem

4.9 out of 5 average rating, 135 reviews

Spacious Historical Home 3 mins from Downtown

Nestled in the historical Washington Park neighborhood, this renovated 1910 home allows you the opportunity to experience life from an earlier era, without sacrificing modern conveniences or decor. Only 3 mins from downtown, it’s conveniently located to most everything you’d need. Whether you are visiting the School of the Arts, the Old Salem Museum, or simply rewarding yourself with a pastry (after your run) at the Award winning Camino bakery, you’ll appreciate how centrally located it is.

Guest favourite

Rental unit in Winston-Salem

5 out of 5 average rating, 258 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!

Guest favourite

Condo in Winston-Salem

4.9 out of 5 average rating, 397 reviews

Sanctuary – 1bedroom & 1bathroom

My modern and convenient condo located in the heart of Winston-Salem’s shopping district will provide you with a 1 bedroom & bathroom space. The condo is professionally furnished and cleaned to provide a 5 star experience. Basic appliances provided (microwave, kitchen appliances, washer & dryer, dishwasher, Keurig). Very spacious with patio furniture for extra relaxation! You can also enjoy the community pool and gym. This space is NOT shared. Guests have the entire space to themselves.

Guest favourite

Guest suite in Ardmore

4.99 out of 5 average rating, 270 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

Guest favourite

Home in Winston-Salem

4.97 out of 5 average rating, 144 reviews

Beautiful 2 BR home with Office and Game Room

This beautifully decorated 2 bedroom home, part of a duplex, comes with high-speed Internet and WiFi. It includes an office and a game room. It is near shopping, hospitals, and the rest of the Winston-Salem scene. kitchen has all the tools needed to prepare your favorite meals. The TV in the living room includes Disney+. Everything except the game room is on the main level. The back deck is ready for hosting a barbecue, with a view of the back yard and adjoining green space.

Guest favourite

Condo in Winston-Salem

4.98 out of 5 average rating, 125 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.

Guest favourite

Home in Ardmore

4.98 out of 5 average rating, 446 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.

Guest favourite

Bungalow in Ardmore

4.96 out of 5 average rating, 367 reviews

Cozy Ardmore Bungalow

Come explore this renovated 1925 bungalow in the historic Ardmore Neighborhood . This sunlit, plant filled home boasts a modern kitchen with concrete counters, gas stove, and hand built wooden furniture. The fenced backyard features a stone patio with fire pit and grill. Smart TVs in each bedroom and living room. Pets are welcome.

Guest favourite

Guest suite in Winston-Salem

4.99 out of 5 average rating, 171 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.