Vacation rentals in Winston-Salem

4.99 out of 5 average rating, 180 reviews

A kitchen cabinet is shown with modern cooking appliances, including an air fryer and an Instapot, both neatly placed on white shelving. A toaster sits alongside these appliances, with a decorative figurine and a cookbook visible on the counter below. The backsplash features a mosaic of circular patterns.

Home in Winston-Salem

The Zen Ranch - Spacious Layout with Modern Decor

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

4.81 out of 5 average rating, 204 reviews

A charming, single-story home is surrounded by a lush green yard and shaded by trees. The exterior features a light-colored facade with a welcoming porch area, and mature landscaping lines the property, enhancing the inviting atmosphere.

Home in Winston-Salem

Winston posh bungalow near Wake

All pets MUST be pre approved prior to booking!!Within 2 miles of Wake Forest, half mile from US- 52 and 20 m High Point. Less than 7 minutes to downtown WS! Convenient to everything, including Pilot Mountain and Hanging Rock State Park. Quality of furnishings are all Higher End. Extremely private setting. IEverything, is as I would have it in my own home. When traveling it makes the experience much more enjoyable, arriving to a well appointed clean living space. A true home away from home!

Apartment in Winston-Salem

An outdoor patio area is presented with a bright orange umbrella shading a small round table and two blue chairs. Lush greenery adds a natural touch to the wooden deck, while a view of nearby buildings and a parking structure is visible beyond the patio.

4.97 out of 5 average rating, 118 reviews

K-Obscura, Romantic Downtown loft

Historic loft in Downtown Winston Salem's Innovation Quarter. Located above Krankies Coffee near WFB Medical School and Bailey Park.Short walking distance to several restaurants and bars. This space has private entrance and patio. Includes complimentary coffee and treat at Krankies. Quiet for a downtown spot with the exception of an occasional train passing through adjacent lot. Includes deep soaking tub, mini-kitchen and comfy king size bed. Space is accessed via stairs. Parking included.

4.89 out of 5 average rating, 283 reviews

A serene outdoor space is presented, featuring two wicker chairs positioned around a circular fire pit. Soft lighting from strung bulbs enhances the environment, while art pieces are displayed on a wooden wall. Decorative plants and gravel complete the cozy retreat.

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 (Closed until 5/23/25) . A fire pit to unwind. 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)

Guest suite in Winston-Salem

A cozy suite is presented with wood paneling and a comfortable sleeping area featuring a patterned quilt on the bed. A dining table with a bowl of colorful fruit is positioned in front, while a fireplace adds warmth to the room. Seating is provided by an upholstered chair.

4.99 out of 5 average rating, 283 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.

Apartment in Winston-Salem

A private rooftop deck is showcased, featuring a dining table and chairs beneath string lights. A grill is positioned nearby, with views of the sunset illuminating the sky. Potted plants are arranged around the space, enhancing the inviting outdoor environment.

4.85 out of 5 average rating, 123 reviews

West End Wonder! Rooftop Deck, Walk Downtown, 2 QN

Take in the West End neighborhood views from our private rooftop deck! Once you’re settled in, stroll down to some of the best restaurants & shops in downtown. Guests will enjoy our newly renovated apartment which is equipped with high speed WiFi, quality mattresses & linens, smart tv, fully equipped kitchen, & more. We offer a complimentary coffee/tea station & toiletries. Shared washer/dryer on site. Traveling with a group? Our property has 3 units that can be booked individually!

Guest suite in Winston-Salem

A spacious bathroom is equipped with a large, white soaking tub positioned beneath a bay window, providing natural light. Elegant fixtures complement the dark tile flooring, while a sleek, glass-enclosed shower and clean, white cabinetry enhance the modern design.

4.95 out of 5 average rating, 142 reviews

Entire COZY Unit - 3 min walk to WFU.

Welcome to your cozy - little net. Please keep in mind that this unit is attached to our house (we shared a wall - different entrance). Everything showed in the pictures will be all yours (Master bedroom, Study room - living room Space, and an extraordinary bathroom). When staying at our place, you are: - 3 min drive (10min walk) to WFU Campus. - 5 min drive to Downtown. - 3 min WALK to Stadiums and Restaurants. - 10min drive to Wake Forest Baptist Hospital. - Reynolda House museum.

4.89 out of 5 average rating, 834 reviews

The kitchen features rustic wooden cabinetry and a large central island with matching wooden benches. Stainless steel appliances are included, with a microwave and stovetop visible. Pendant lights illuminate the space, creating a warm and welcoming atmosphere.

Cabin in Ardmore

Log Cabin in the city, w/Brewery Tour and Tasting

READ ENTIRE LISTING! NO PARTIES/ GATHERINGS. Only the guests on the reservation are allowed to be on my property. I WILL KICK YOU OUT AND CALL THE COPS. I DO NOT PLAY GAMES. The listing is the entire UPPER LEVEL of my log cabin, which is conveniently located less than a mile from Downtown Winston-Salem! The back yard is surrounded by woods and a privacy fence with a hammock and fire pit that is available to use! Great place close to downtown. NO SMOKING of any kind allowed anywhere.

4.96 out of 5 average rating, 481 reviews

A hammock is positioned comfortably on a grassy area, surrounded by lush greenery. Sunlight filters through the trees, creating a serene atmosphere. Nearby, a covered picnic shelter is partially visible, featuring seating for relaxation.

Guesthouse in Germanton

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.

4.97 out of 5 average rating, 570 reviews

A spacious bedroom features a wooden bed with a gray quilt and decorative pillows. Two bedside tables with lamps flank the bed, and a window allows natural light to fill the room. A framed picture adorns the wall above the bed.

Home in Ardmore

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.

4.94 out of 5 average rating, 364 reviews

The laundry area features a stacked washer and dryer beside a modern art piece mounted on a light gray wall. A striped laundry basket is positioned nearby, while a decorative round woven basket is placed on the floor, adding functional storage.

Condo in Winston-Salem

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!

Apartment in Winston-Salem

The exterior of a modern home is presented with light brown siding and dark shutters. Two garage doors are featured at the front, flanked by potted plants. A clear sky and trees are visible in the background, enhancing the serene setting.

4.99 out of 5 average rating, 122 reviews

Executive Escape

A well appointed and modern space for those looking for a home away from home. Wether you're visiting family and friends, or on assignment, this space has all you need while visiting Winston Salem. Located in a quiet and mature neighborhood, you'll find easy access to the local hospitals and WFU. Local shops, eateries and things to do also ...

Vacation rentals for every style

Get the amount of space that is right for you

Cabins

Kick off your hiking boots at these rustic lodgings

Houses

A space thats all yours, with room for everyone

Apartments

Convenient locations with everyday essentials

Popular amenities for Winston-Salem vacation rentals

Vacation rentals with jacuzzis in Winston-Salem

4.88 out of 5 average rating, 133 reviews

A modern dining area features a sleek black dining table surrounded by six chairs. Stylish green accent chairs complement the decor. Bright green wall sconces and a round mirror enhance the ambiance, while framed artwork hangs elegantly on the walls. Natural light enters through a window draped in light curtains.

Home in High Point

Luxe Hot Tub 4BR: Ideal for Market, HPU & Families

4.92 out of 5 average rating, 250 reviews

The charming farmhouse presents a welcoming facade with classic architectural details. A large porch is adorned with white railings, while a pathway leads through a grassy area. The home is surrounded by trees and features a light-colored exterior complemented by decorative trim.

Home in Mayodan

Home away from home.. 20 minutes-Greensboro/Triad

4.9 out of 5 average rating, 177 reviews

A charming private home is set within a spacious green yard, surrounded by mature trees. A brick chimney rises from the roof, while a pathway leads to the entrance, creating a welcoming entry. The tranquil atmosphere of the outdoors is enhanced by the natural surroundings.

Home in Summerfield

Private. Hot Tub & Movie Den. 7 mins to Airport

4.98 out of 5 average rating, 138 reviews

A workout room is shown, featuring a wooden sauna with glass doors and a treadmill positioned beside it. Fresh towels are stacked on a shelf nearby, and large windows allow natural light to fill the space, complemented by neutral-colored walls.

Home in Greensboro

Relax at Beck & Call Sauna, Hot tub, mini-Gym

5 out of 5 average rating, 20 reviews

A spacious living area features a large sectional sofa arranged around a wooden coffee table. Natural light flows through tall windows above, highlighting the wooden floor and neutral wall colors. Decorative wall art adds a subtle touch, while a lamp and a plant complete the inviting space.

Home in Greensboro

Everything You Need

4.99 out of 5 average rating, 128 reviews

An open living area features a stone fireplace as the focal point, surrounded by large windows that allow natural light to illuminate the wooden walls and ceiling. A cozy seating arrangement, including a dark sofa and coffee table, complements the cabin's rustic charm.

Cabin in Lewisville

Cozy renovated 3 bedroom cabin with hot tub

4.88 out of 5 average rating, 258 reviews

A serene outdoor space features a hot tub surrounded by wooden decking. A projected movie screen displays an ocean scene, illuminated by soft lights. The area presents a perfect setting for relaxation and entertainment at night.

Home in High Point

Wayne's Place-Hot tub, pet friendly. Close to HPU

5 out of 5 average rating, 356 reviews

A two-story wooden house is surrounded by greenery, with a driveway leading up to the entrance. A deck is visible on the left side, offering a vantage point of the landscape. The entrance features a staircase leading up to the main level.

Guesthouse in Lexington

Mountain View Retreat

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Other great vacation rentals in Winston-Salem

4.92 out of 5 average rating, 118 reviews

Home in Walnut Cove

Modern and Spacious cottage, centrally located

4.93 out of 5 average rating, 199 reviews

A handcrafted log cabin features a spacious porch with wooden rocking chairs, surrounded by a grassy area. Large windows allow natural light to fill the interior. The structure is designed for accessibility, with a gentle ramp leading to the entrance.

Cabin in Pilot Mountain

2 bedr 2 baths Custom Log Cabin on Pilot Mtn Farm

4.98 out of 5 average rating, 176 reviews

A modern kitchen is showcased with white cabinetry and granite countertops. Appliances include a refrigerator, oven, and dishwasher. Shelves display plants and books. A laundry area is visible with stacked washer and dryer units, providing convenience and functionality.

Home in Jamestown

Downtown Jamestown, quiet, clean and spacious!

4.95 out of 5 average rating, 170 reviews

A cozy outdoor space features a square fire pit table surrounded by four bright blue Adirondack chairs. The area is bordered by lush greenery and trees, with a spacious lawn visible in the background. A shaded structure is seen in the distance.

Cottage in Greensboro

⭐️ Amelia’s Retreat ⭐️ @ Greensboro 🐕📚🏊‍♀️🏥

4.96 out of 5 average rating, 327 reviews

Two armchairs with yellow cushions are positioned beside a round, upholstered ottoman, which also serves as a coffee table. A potted plant is displayed atop the ottoman, creating a cozy relaxation area. The ceiling features wooden beams, adding a touch of warmth to the space.

Tiny home in Jamestown

Tiny House

4.96 out of 5 average rating, 102 reviews

An illuminated driveway is lined with white fencing, guiding the way to the garage. Soft lights highlight the gravel landscaping alongside the path, creating a welcoming atmosphere in the serene evening setting. Trees are visible in the background, adding to the peaceful environment.

Home in Belews Creek

Deer Hill - 1450 sq. ft. of Comfort & Convenience

4.96 out of 5 average rating, 148 reviews

A spacious outdoor deck is presented, featuring two blue lounge chairs with a relaxed design. A green and a red accent table are included, enhancing the colorful atmosphere. The backdrop consists of tall trees, creating a sense of seclusion and connection to nature.

Cabin in Pinnacle

Lizard Lookout