Holiday rentals with a pool in Winston-Salem

Beautiful Retreat at Pilot Mountain Vineyards

This quiet rancher sits right off of HWY 52 in Pinnacle, NC. The property is connected to Pilot Mountain State Park on two sides. PMSP trails can be accessed from here. Right down the road, there is a river access to the Yadkin River and horseback riding trails. Hanging Rock state park and the Dan River are only a few miles away. The historic town of Pilot Mountain is down the road. Enjoy the beautiful view of the mountain and the feel of being isolated while close to restaurants and activities

HotTub; Game Room; Gym; Spacious4Groups

POOL CLOSES OCT 1!! Experience the ultimate getaway in this spacious 5-bedroom, 4.5-bath home that sleeps up to 20 guests. Highlights include a pool, 4-person hot tub, expansive yard, and a screened-in porch. Enjoy endless entertainment in the game room with pool table and ski ball or stay active in the gym with a sauna. Perfect for reunions or retreats, this oasis is close to Winston-Salem, Greensboro, and High Point. Relax, recharge, and create unforgettable memories in this luxurious retreat!

Historic Street House/Hot Tub

Walking distance to Furniture Market , Hospital, Baseball Stadium, Children’s Museum, High Point University, Carolina Core Soccer, Uptowne shops, Restaurants, Breweries, Alex's House, a local breakfast diner, Dinner at Sweet Ol Bill's or the Historic JH Adams Inn. Live Music within walking distance. Nearby Greenway/Pickleball Courts. Joy Bar coffee 2 blocks away.Saturday Farmers Market. Library, Krispy Kreme, Relax on the front porch or ping pong inside! Back yard Hot Tub. 10 foot plunge pool.

Guest House at Tall Tree Manor

Discover the perfect getaway at our renovated guest house, nestled on a picturesque 35-acre country estate along the Yadkin River in Clemmons, NC. Minutes from Tanglewood, and a quick 15-min drive to Wake Forest, this property offers the best of both worlds. Relax in the living room, where a cozy electric fireplace invites you to unwind, or savor the peaceful surroundings from the charming front patio. Embrace the tranquility of country living while staying close to vibrant city attractions.

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)

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.

Pearlitah: Cozy 3-BR, King Suite – Winter Escape

Nestled in a serene, semi-gated community, Pearlitah is a newly-renovated 3-BR townhouse in Greensboro that blends luxury with comfort. The master suite features a California King bed, and the home comfortably sleeps up to 9. Just 14 minutes from GSO airport, with easy highway access, and walking distance to local eateries and shops, Pearlitah offers a tranquil yet connected retreat. Ideal for relaxation and exploration, it’s the perfect home-away-from-home in this charming residence.

Adult Getaway @ The Cave

Tucked away in the peaceful Sedgefield PGA community of Greensboro, The Cave is a 2-bedroom, 1-bath poolside suite designed for relaxation & comfort. This serene grown-up getaway boasts luxury amenities including exclusive use of our private seasonal pool, indoor & outdoor theaters, Brunswick pool table, bar/ kitchenette, & more. Enjoy personalized service & a prime location—just minutes from top dining, shopping, golf courses, entertainment venues, sports arenas, & universities.

Entire Private Entrance Studio Apartment with Pool

This private entrance, NOT shared, spacious open plan apartment includes a king bed, sofa, dining area, work space, plus a private full bathroom. The living space is located on the 2nd floor and the bathroom is on the ground floor. There are 15 stair steps between the 2 levels. The property is located 1-1/2 miles from downtown Mocksville and Interstate 40. Travel time is 25 mins to Winston-Salem & Wake Forest University, 22 mins to downtown Statesville, & 24 mins to Salisbury.

Aqua Oasis - Central & Stylish - 3 BR / 3 BA

Located within a desirable, quiet and leafy neighborhood is this modern townhouse offering chic style, elegant design and everything you could need for a relaxing stay. Inside you’ll enjoy open plan living, a large kitchen, 3 beautiful bedrooms with smart TVs, sparkling bathrooms and a gorgeous private patio. Stay only mins from restaurants, bars & breweries and only a short drive to Downtown, Bicentennial Garden, hospitals, The Friendly Center, and the Greensboro Coliseum.

Amazing Retreat Outdoors+Indoors

I’m Tom, a design-build professional & my wife Lindy’s background is international furniture. We’ve combined our talents to create this retreat with BEAUTIFUL interior & WONDERFUL outdoor amenities: Lush landscaping, heated salt water pool (POOL IS HEATED FROM THE LAST WEEK OF APRIL THRU THE FIRST WEEK OF OCTOBER), cedar barrel sauna and hot tub. We created this retreat for ourselves but do rent it on a limited basis to other FAMILIES to create wonderful FAMILY memories.

Pool and Hot Tub | Stunning home

This beautifully staged 4-bedroom, 3,5 bath home in Lewisville, NC, sleeps 7 and offers the ultimate relaxation with a private pool, hot tub, and outdoor dining space. Inside, enjoy a spacious open-concept living area and a fully equipped kitchen. Located minutes from top wineries, a distillery, and a brewery, it’s the perfect home base for exploring local flavors. Whether you’re lounging by the pool or touring nearby attractions, this retreat has it all!