Vacation rentals in Winston-Salem

A small outdoor balcony features two white chairs positioned near a potted plant. The railing is painted black, contrasting with the deck's dark surface. Lush green trees are visible in the background under a partly cloudy sky, creating a serene outdoor space.

4.81 out of 5 average rating, 202 reviews

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!

The exterior of the home presents a well-maintained façade with a white siding and a two-car garage. A generous driveway is flanked by green grass and shrubs. A flag gently flutters from the front, while a shaded seating area is visible in the yard.

4.85 out of 5 average rating, 115 reviews

Updated Hidden Gem- Kernersville/Winston-Salem

Beautiful fully renovated home welcomes you with bright completely new kitchen, all new stainless steel appliances. Fresh paint throughout interior and exterior. Brand new light fixtures and ceiling fans. Newly updated bathrooms. New carpeting and new luxury flooring throughout. Beautiful yard, family friendly neighborhood. Excellent Wifi, 2 TVs in house (one in living room and one in main bedroom). Shopping including grocery stores, gas stations, restaurants are all a quick 3 minutes away.

Apartment in Winston-Salem

A private rooftop deck is showcased with two wooden chairs facing a sunset view, string lights overhead providing soft illumination. A patterned rug anchors the space, complemented by a small table and potted plants. A barbecue grill and additional seating are also present.

4.84 out of 5 average rating, 121 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!

4.95 out of 5 average rating, 310 reviews

A charming white cottage is set against a backdrop of tall trees and an expansive snowy yard. The front porch features four black chairs and is adorned with wreaths. Steps lead up to a dark entrance door, welcoming guests into the cozy space.

Tiny home in Jamestown

Tiny House

PLEASE READ BEFORE BOOK (ONLY 2 PEOPLE ALLOWED INCLUDING CHILDREN’S) Keep it simple at this peaceful and lovely tiny house . Our place is located just 15 mins from UNC Greensboro, High Point university, Greensboro Coliseum, four season mall ,friendly shopping center and Downtown Greensboro and Highpoint ,only 5 mins away downtown of Jamestown. Convenient distance for our furniture market High Point and Furnitureland South. Restaurants and grocery stores are only 5 mins away.

The kitchen features modern appliances, including a white refrigerator and an oven with a microwave above. A marble countertop offers a spacious area for food preparation. Decorative tile backsplashes complement the cabinetry, illuminated by pendant lights above. A small clock and potted plant add decorative touches.

4.9 out of 5 average rating, 265 reviews

1940s Stunner. Pets Welcome. Prime HPU Location!

Welcome to Emoryview II, our lovingly restored 1940’s home in High Point! Located in a safe, quiet, and picturesque neighborhood, we're a quick drive to everything. We're minutes from Main St, giving you easy access to dining, bars, HPU, Furniture Market (only 2 miles away!), and the highway. We're fully equipped with all the amenities of home, making us an excellent choice for business travel, visiting family, college visits, weddings, and other events that bring you to the area.

4.98 out of 5 average rating, 170 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!

Location is key! A block from quaint Jamestown's food and entertainment. Five miles from Furniture Market, four miles from HPU, 8 miles from downtown Greensboro or coliseum area and less than 20 miles from Winston. Adorable ranch, recently updated and has all the comforts of home. Pet friendly with fully fenced backyard. Both business travelers and families will enjoy the safe , quiet neighborhood walking distance to dining, coffee shop, bakery, entertainment, parks and trails.

4.9 out of 5 average rating, 173 reviews

A round window framed by warm brick displays a serene winter scene. Soft snow falls on the ground outside, with evergreen trees partially visible in the background, creating a peaceful atmosphere.

Home in Summerfield

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

Private secluded property surrounded by Autumn trees only 10 minutes from GSO airport, activities, and the center of Greensboro. Take your coffee on the small covered porch for a chance of a glimpse of a deer. Inside you'll find a comfortable worn kitchen fully stocked with the essentials (feel free to make chocolate chip cookies!) order additional groceries from instacart and never leave the house, or go for a nearby outing on the lakes, trails, or tour the historic area.

A well-lit hallway features hardwood flooring and white walls, leading to a staircase with wooden steps and black iron railings. Vintage sliding doors, adorned with green and blue patina, separate the hallway from the living area, adding a unique character to the space.

4.94 out of 5 average rating, 109 reviews

The Farmhouse Retreat near Furniture Mkt and HPU

Welcome to The Farmhouse Retreat in High Point! It is a thoughtfully remodeled 100 year old Farmhouse that lives minutes away from the Furniture Market and High Point University in the popular historic district! Conveniently located within walking distance to many popular local restaurants and breweries as well as the Rockers Baseball Stadium! While this adorable home is the perfect private getaway for you and the family, its location makes it easy for you to get around.

4.91 out of 5 average rating, 114 reviews

Home in Walnut Cove

Modern and Spacious cottage, centrally located

Peaceful and centrally-located place. You will have everything you need at this beautiful home away from home. Perfect for families, couples, or singles. Bring your fur babies along. $20/pet per night - 5 min from chateau vie wedding venue -20 min from Hanging Rock State Park -walking distant from local restaurants, coffee, and shops. - 10 min from Belews Lake -12 min from Duke Energy -20-30 min from Winston-Salem -30 min from GSO -15 minutes from The Meadows

4.97 out of 5 average rating, 241 reviews

The charming exterior of a renovated Craftsman bungalow features a welcoming front porch with white railings and a gray door. A landscaped yard with green grass and lush shrubs is visible, bordered by a wooden privacy fence. Natural light highlights the structure under a clear sky.

Bungalow in High Point

Historic Walker House Adj. to JH Adams Inn

Stay in one of High Points treasures! Historic Renovated Robert Walker House is ready for guests to enjoy! Non-owner occupied means you won't be sharing personal space with owners :)Beautifully decorated open floor plan and kitchen/dining seats 12. Home has designer furnishings with flat screens in all. 3 BR 2.5 bath !Walk to restaurants and award winning craft brewery in downtown HP. Minutes to High Point University and HPMKT and new Rockers Baseball Stadium!

4.96 out of 5 average rating, 478 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.

4.95 out of 5 average rating, 166 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 🐕📚🏊‍♀️🏥

Our vision with this property was always clear and consistent as with all of my other properties. We wanted to combine all our favorite features from various Airbnb stays around the world under one roof. We hope that we have accomplished just that, and we are always grateful for any tips that can help us get closer to this goal. At Amelia’s retreat your family will be close to everything at this centrally-located Greensboro gem. Permit # 24-511

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

Self check-in

Pet friendly

Laptop-friendly workspace

Hot tub

Gym

Stay near Winston-Salem's top sights

Old Salem Visitor Center149 locals recommend

Reynolda House Museum of American Art99 locals recommend

Benton Convention Center8 locals recommend

Village Tavern84 locals recommend

Whole Foods Market64 locals recommend

Mozelle's Fresh Southern Bistro60 locals recommend

Pet-friendly vacation rentals in Winston-Salem

A comfortable living room features leather seating and a wooden entertainment unit. Two side tables with lamps flank a cozy chair, providing warm lighting. A decorative painting hangs on the wall, and a small plant adds a touch of greenery. The laminate flooring creates a unified look.

4.96 out of 5 average rating, 160 reviews

Cozy 3 Bedroom Home with Fenced Back Yard

Guesthouse in Winston-Salem

The exterior of the cottage is visible, showcasing a charming garden courtyard with various plants and trees. A brick pathway leads to the entrance, along with a unique swing and outdoor decor. Soft lighting and a welcoming atmosphere can be seen throughout the space.

4.93 out of 5 average rating, 845 reviews

Courtyard Cottage Safe Parking! No pet fees!

4.97 out of 5 average rating, 115 reviews

Guesthouse in Mocksville

“Home” on the Road!

5 out of 5 average rating, 104 reviews

Cabin in Lexington

Klump Farm Cabin

4.98 out of 5 average rating, 173 reviews

A charming guesthouse is nestled among trees, showcasing a dark exterior complemented by orange shutters. A walkway leads to the white front door, framed by seasonal plants. Leaf-covered ground adds to the rustic setting, emphasizing the tranquil surroundings of this private retreat.

Guesthouse in Archdale

Hillbilly Hideout

4.94 out of 5 average rating, 270 reviews

The log cabin features a green metal roof and a stone chimney. A welcoming porch is supported by wooden beams and lined with flower baskets. Lush green grass surrounds the structure, complemented by trees in the background, creating a serene outdoor setting.

Cabin in Summerfield

Cozy chic log cabin overlooking horse pastures

4.98 out of 5 average rating, 100 reviews

The modern farmhouse exterior features a stepped roof with a metal finish, complemented by inviting covered porches. Lush greenery and ornamental plants line the pathway, while a broad grassy area extends, providing a serene connection to nature.

Home in Lexington

Duke's Place - Tranquil Farmhouse Retreat

4.88 out of 5 average rating, 158 reviews

The kitchen features light wood cabinetry and blue laminate countertops. Equipped with a full set of appliances including a stove, microwave, and refrigerator, ample workspace is provided. Three bar stools with patterned fabric are situated at the counter, enhancing the inviting cooking area.

Apartment in Summerfield

Cozy Apartment on Mini Farm!

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House rentals in Winston-Salem

5 out of 5 average rating, 13 reviews

A comfortable living room setup is featured with a gray sofa adorned with various pillows. A matching armchair complements the space, which is warmly lit by a standing lamp. A round coffee table sits on a soft rug, with sunlight filtering through windows adorned with light curtains.

Home in Greensboro

Perfect Greensboro location Entire Townhome

A modern living area is showcased, featuring a comfortable seating arrangement with a patterned sofa and neutral-toned chairs. A wooden coffee table is centered in the space. The adjacent open kitchen is visible, equipped with stainless steel appliances and light cabinetry, enhancing the airy atmosphere.

5 out of 5 average rating, 19 reviews

Premium Retreat close to WFU w/ Lvl 2 EV Charger

4.81 out of 5 average rating, 120 reviews

A comfortable living space is presented, featuring a light-colored coffee table at the center. A blue armchair and a gray sofa offer seating options. Two mirrors are positioned across from the doorway, while a television is mounted on a stand against the wall.

Home in Kernersville

Quaint 2 bed 1 bath cottage style home

A single-family home features a light-colored exterior with blue shutters. A large, attached garage is visible, with a paved driveway leading to it. The front yard is well-maintained, showcasing shrubs and a tree with vibrant autumn foliage.

4.93 out of 5 average rating, 180 reviews

"Deacon House" 3 bedrooms

The image depicts a charming single-family home with blue siding situated on a well-maintained lawn. Trees and shrubs surround the house, contributing to a serene atmosphere. A driveway is visible in front, allowing easy access to the property.

4.97 out of 5 average rating, 115 reviews

High Point Hideaway

A spacious living area showcases two reclining sofas in rich brown leather, accompanied by a wooden coffee table with a checkered design. Large windows are adorned with light curtains, allowing natural light to brighten the space. A wall displays the phrase 'Stay awhile' in elegant script.

4.92 out of 5 average rating, 61 reviews

Spacious Townhouse In High Point Near HPU & Market

An urban scene showcases a modern complex with brick and glass buildings. A large mural reading 'Compton Yards' is prominently displayed on one structure. The area is well-maintained, featuring landscaped greenery and a pathway. Clear blue skies create a bright backdrop for the architectural diversity.

4.75 out of 5 average rating, 4 reviews

Convenient Downtown Lodging

A dining area is highlighted by a modern glass table surrounded by black chairs. Elegant red curtains frame the windows, and a piece of wall art featuring a vase and flowers complements the decor. A large refrigerator is positioned beside the table.

4.83 out of 5 average rating, 63 reviews

3 bedrooms close to downtown, Hospital & college

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Vacation rentals with jacuzzis in Winston-Salem

4.87 out of 5 average rating, 52 reviews

An outdoor deck area features a hot tub and wooden flooring, surrounded by trees. A staircase leads to an upper level of the house, while a rocking chair and additional seating are present, providing a cozy space for relaxation.

Home in Belews Creek

Belews Lake Paradise

A private hot tub is situated in the fenced backyard, surrounded by well-manicured grass. The clear blue water reflects the sunlight, offering a relaxing environment for guests to unwind.

4.88 out of 5 average rating, 129 reviews

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

A private outdoor space features a round stock tank pool surrounded by a pebbled area. Two colorful inflatable pool toys rest in the water. Comfortable seating arrangements with woven chairs are paired with hammocks, creating a cozy atmosphere amidst lush greenery.

4.89 out of 5 average rating, 275 reviews

Cozy King Blue H2O Staycation , Pool & Hot Tub

4.9 out of 5 average rating, 21 reviews

A spacious backyard features a basketball court, complete with a hoop and smooth concrete surface. A charming outdoor lounge area is visible on the deck, surrounded by lush greenery, while the home’s exterior showcases a modern design set against a serene natural backdrop.

Home in Jamestown

The Arlington Oasis | Sport Court + HotTub + Golf

5 out of 5 average rating, 17 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

Tiny home in Winston-Salem

A wooden deck is shown in the image, featuring two lightweight chairs positioned beside a hot tub. A covered structure is visible nearby, providing a shaded area. Tall trees surround the space, contributing to a serene woodland setting.

4.92 out of 5 average rating, 76 reviews

Hot Tub Hideaway

4.99 out of 5 average rating, 128 reviews

A hot tub is positioned on a wooden deck, with bubbling water visible. Surrounding trees display autumn foliage, creating a warm atmosphere. The deck features a black railing and overlooks a wooded area, inviting relaxation in a tranquil outdoor setting.

Cabin in Lewisville

Cozy renovated 3 bedroom cabin with hot tub