
Vacation rentals with a pool in Winston-Salem
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Winston-Salem
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

Adult Retreat • 13 mi to PTI • Private Pool & More
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.

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

Peaceful Ardmore 2BR 5 min to hospitals & downtown
Keep it simple at this peaceful and centrally-located condo with ample natural lighting in Ardmore. Dedicated work space in bedroom with double bed (pictures to be updated soon). Walking distance to restaurants and shopping and right around the corner from interstate. 5 min drive to downtown area. Walking distance to Atrium Health Wake Forest Baptist Health, less than 2 miles to Novant Health Medical Park/Forsyth Medical Center. 8 mins to Hanes mall area. ~10 min drive to Wake Forest University.

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.

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.

Grey Sapphire Hideaway - 2BR/2BA w/ Arcade
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!

Historic Street House/Hot Tub
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!

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, 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.

Light and Bright Condo - WFU, Atrium Hospital
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. Easy 4 min drive/20 min walk to WF Baptist Medical Center. Prime location for shopping + dining with a 2-10 min walk to Camel City Coffee, Bagel Station, Harris Teeter grocery, Trader Joes and over 40 dining and shopping choices.
Popular amenities for Winston-Salem rentals with a pool
House rentals with a pool

Hot tub | Fire-pit | Pool Table | Heated Pool

Belews Lake Paradise

Poolside Retreat: Greensboro, High Point, Winston

The Little House #4

Lakefront Retreat with Private Indoor Heated Pool

Private 4BR w/ Heated Pool, Hot Tub & Fire Pit

Henry Connor Bost House

Fun Home w/ Backyard Oasis | Near Downtown GSO!
Condo rentals with a pool

2br King-Queen/2ba/Pool/ No cleaning fees!

Location, Location, Location /Pool/2BR King Stay

Comfortable Condo for Work or Leisure-Pool&Shops

Modern/Retro Luxury Condo

The Best of Benjamin

Heaven in High Point / Luxury 1bd/1ba

Comfy townhouse near airport and dining!

3BR Condo w/ Pool Near HPU & Market + Desk
Other vacation rentals with a pool

The Haven

Serene Woodland Loft with Pool – Entire Building

5 Min to High Point Market | Sleeps 8 | Near HPU

Remodeled Oasis in the heart of Greensboro

Entire Private Entrance Studio Apartment with Pool

Extended Stay 1BD Apt | Near Cone Health + I-40

Carolina Cottage

5 Star Weddings, Pool!, Early Chck, Nearby Fishing
When is the best time to visit Winston-Salem?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $157 CAD | $159 CAD | $152 CAD | $159 CAD | $159 CAD | $159 CAD | $152 CAD | $157 CAD | $152 CAD | $163 CAD | $167 CAD | $177 CAD |
| Avg. temp | 4 °C | 6 °C | 10 °C | 15 °C | 20 °C | 24 °C | 26 °C | 25 °C | 22 °C | 16 °C | 10 °C | 6 °C |
Quick stats about vacation rentals with a pool in Winston-Salem

Total vacation rentals
Explore 80 vacation rentals in Winston-Salem

Nightly prices starting at
Winston-Salem vacation rentals start at $28 CAD per night before taxes and fees

Verified guest reviews
Over 2,240 verified reviews to help you choose

Family-friendly vacation rentals
30 properties offer extra space and kid-friendly amenities

Pet-friendly vacation rentals
Find 30 rentals that welcome pets

Rentals with dedicated workspaces
60 properties have a dedicated workspace

Wifi availability
80 of Winston-Salem vacation rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Winston-Salem rentals

4.6 Average rating
Winston-Salem stays receive an average rating of 4.6 out of 5 from guests
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- North Carolina Zoo
- Hanging Rock State Park
- Pilot Mountain State Park
- Wet'n Wild Emerald Pointe Water Park
- Zootastic Park
- Greensboro Science Center
- Stone Mountain State Park
- Lazy 5 Ranch
- Lake Norman State Park
- Wake Forest University
- Greensboro Coliseum Complex
- International Civil Rights Center & Museum
- University Of North Carolina At Greensboro
- Childress Vineyards
- Fairy Stone State Park
- Guilford Courthouse National Military Park
- Reynolda Village Shops & Restaurants
- Elon University
- North Carolina Transportation Museum
- Shelton Vineyards
- Andy Griffith Museum
- Martinsville Speedway
- Greensboro Arboretum
- Cherry Treesort





