Vacation rentals with a pool in Winston-Salem

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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

The Cave • Adult Oasis • Pvt Pool Open until 9/20

Tucked away in the peaceful Sedgefield PGA community of Greensboro, The Cave is a 2-bedroom, 1-bath poolside GUEST SUITE designed for relaxation & comfort. This serene grown-up getaway boasts luxury amenities including exclusive use of our private seasonal (summer) 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.

Modern/Retro Luxury Condo

Unique condo with brand new Ultra Modern renovation with a touch of Retro. If you seek an Extremely Clean, Modern Luxurious place close to everything then this is it. My place is in walking distance to all shopping and restaurants. High Point University only ( 1.8miles ), HP Furn Market is only ( 2.3 miles ).Kitchen is fully stocked, all luxury linens, shampoo, soap, toilet paper are included. Hearing impaired doorbell. Led TV's with Netflix,Amazon & whatever channels come in on regular antenna.

Light and Bright Condo w/POOL - WFU, Atrium Hosp

About this space You will love the peaceful feel of this light filled condo with designer touches, located in walking distance to so many conveniences. Located less than 1 mile to WF Baptist Medical Center; 3.5 mile /10 min drive to WFU and NCSA. Prime shopping + dining with a 2-10 min walk to over 40 dining and shopping options including Camel City Coffee, Bagel Station, Harris Teeter grocery, and Trader Joe’s. Explore the popular Ardmore neighborhood with sidewalk lined streets and parks.

Cozy & Convenient

***Accepting shorter stays*** Keep it simple at this peaceful and centrally-located place. Enjoy the sidewalks throughout this beautifully laid out neighborhood. I’m the summer, take advantage of the twenty five meter pool at the end of road. Two bedrooms, both rooms are en suites. Living room, kitchen are open concept lay out with lots of storage. Washer and dryer are in the unit downstairs. Lots of natural light to enhance the setting. You will have the whole entire townhouse to yourselves.

Private Pool; HotTub; Game Room; Gym

POOL CLOSES OCT 6! 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!

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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. PET FEE $50 per dog.

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)

“Deacon Townhouse” 3 bedroom

Perfect Family Getaway! Discover your ideal home retreat in this spacious and comfortable accommodation, perfect for group of 6 people or families seeking memorable stay. You’ll enjoy access to fantastic community playgrounds and a refreshing swimming pool, ideal for fun-filled days. This inviting home features 3 cozy bedrooms and 2.5 bathrooms, providing ample space and privacy for everyone. Engage in friendly competition with the pool and ping pong table promising ours of entertainment.

Grey Sapphire Hideaway - 2BR/2BA, Game Room & Pool

Nestled along a leafy tree-lined street in a quiet neighborhood is this stylish property with all the modern comforts of home and an inviting community pool waiting for you to enjoy. Inside this modern hideaway, you’ll find plush sofas, a warm fireplace, a gourmet kitchen, king and queen bedrooms and a bright sunroom filled with a Pac-Man arcade & an air hockey table. Centrally located only minutes from Hanes Mall, Downtown Winston Salem, Medical Centers, shops, restaurants, and more!

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Historic Street House/Hot Tub/Splash Pool/Chickens

3 min. drive to Furniture Market, Hospital, Truist Point Baseball Stadium, Children’s Museum. High Point University, Carolina Core Soccer 1 mile away. Uptowne shops, Restaurants, Breweries, Alex's House Diner, Toms Place, Sweet Ol Bill's, Historic JH Adams Inn less than a mile away. Weekend Live Music, Greenway/Pickleball Courts. Joy Bar coffee 2 blocks away. Farmers Market. Library, Krispy Kreme, Relaxing front porch or ping pong inside! Hot Tub. 10 foot plunge pool. Backyard chickens!

Townhouse near the Airport

Welcome to my home! Ideally located just 5 minutes away from the PTI airport, this home boasts a convenient main level primary bedroom with Spacious Living Room and Kitchen. Upstairs, you'll discover a cozy and inviting loft, a second bedroom, and a bathroom. The home also includes a well-equipped kitchen, perfect for cooking your own meals or eating taking out. The living room features a cozy fireplace and Apple TV for your entertainment. I look forward to hosting you!