Vacation rentals with outdoor seating in Winston-Salem

5 out of 5 average rating, 47 reviews

A charming cabin is set amongst tall trees, with a winding driveway leading to its entrance. The house features a multi-level structure and large windows. The surrounding area is covered with fallen leaves, indicating the seasonal changes in nature.

Home in Lewisville

Hidden Gem mins from winston/cooperate & long term

Feel like in wood ready to camp out this beautiful home give you blink of the camping , setting campfire at night and enjoying hot beverages with your group. All amenities to fit any needs work from home got the perfect office place to set up with fast wifi and nighthawk router, living room open space to cook your favorite meal and enjoy game of chess on life size chess table or shoot pool. At night great place to play board games like Monopoly, uno and cards. Three level home have full privacy.

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, 116 reviews

High Point Hideaway

Enjoy a well maintained 3 bed/2 bath single-family home in a quiet neighborhood only a short drive from all that High Point and the surrounding area have to offer. Perfect for visiting friends and family at High Point University as well as within the rest of the Triad area. 2 mi to High Point University 1.9 mi to Harris Teeter & Publix 1.5 mi to Oak Hallow Golf Course, Tennis Center, Marina, &Campground 13 mi to GSO Airport 3 mi to downtown High Point 15 mi to Greensboro 18 mi to Winston-Salem

4.86 out of 5 average rating, 7 reviews

The exterior of the home is illuminated at night, highlighting a cozy patio area with multiple round tables and elegant chairs. String lights create a warm ambiance, accentuating the inviting entrance and well-kept landscaping, suitable for evening gatherings.

Home in Winston-Salem

Private oasis right in town

The home is on a 3-acre property and it always feels like vacation around here! Bedrooms are spacious & inviting. Beds sleep up to 8, extra available. In the backyard you'll find a gas grill, comfortable deck next to a fire pit and a walking trail through an acre of woods. Kids can jump on the trampoline or zip down the zip line. Pick up a game of badminton, or relax in the hammocks for absolute peace and quiet. Make your home away from home in our beautiful, convenient & quiet neighborhood.

An outdoor patio area is featured, showcasing a round black table surrounded by four wooden chairs. A comfortable sectional sofa is positioned nearby, all set against a backdrop of lush greenery and mature trees, creating a serene outdoor environment.

4.97 out of 5 average rating, 103 reviews

<2mins to HPU w/cornhole,billiards,firepit&games!

Welcome to our beautiful mid-century modern Cape Cod! You'll enjoy being close to everything that makes this town special. ♥The Farriss House♥ is walkable to High Point University (.5m), family friendly Armstrong Park, the High Point Greenway, Quebein Children's Museum, Rocker's baseball stadium, Stock+Grain Assembly food hall,&Congdon Yards! This space was designed for gathering and making lasting memories. Enjoy recent updates to this 1940's home that has maintained much of its original charm

4.93 out of 5 average rating, 103 reviews

Historic Street House/Hot Tub

Walking distance to Furniture Market , Hospital, Baseball Stadium, Children’s Museum, High Point University. Uptowne shops, Restaurants, Breweries, Alex's House, a local diner for breakfast, Dinner at Bill's or the Historic JH Adams Inn. Live Music within walking distance. Nearby Greenway/Pickleball Courts. 83 Coffee 2 blocks away.Saturday Farmers Market. Library, Krispy Kreme, Relax on the front porch or ping pong inside! Back yard Hot Tub. House is not suitable for children under 10 years.

Superhost

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.

Home in Winston-Salem

4.89 out of 5 average rating, 278 reviews

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 . A fire pit to unwind. Double Hammock & Enjoy a 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)

4.98 out of 5 average rating, 192 reviews

A well-equipped kitchen features white cabinetry and stainless steel appliances, including a refrigerator and oven. A central island with two modern bar stools provides a casual dining space. The warm wood flooring complements the design, creating an inviting cooking environment.

Apartment in Statesville

A place for you in the country

You'll love or Carriage House. Full kitchen with oven, French door refrigerator, stove, microwave. Has an island where you can eat or a dining table with 4 chairs. Washer and drier. Dedicated workspace. Large sectional sofa and coffee table. Entertainment includes 55 in Smart TV & High speed internet Queen bed & all linens. Also cotton sheets Bath has walk in frameless shower. Entire space is well lit. A place you'll visit again & again. Comfort in the country. We welcome you to our place.

4.97 out of 5 average rating, 181 reviews

<5min to HPU & Market *The Historic Escape*

We are 𝐉𝐨𝐡𝐧𝐬𝐭𝐨𝐧 𝐄𝐬𝐜𝐚𝐩𝐞𝐬 and we welcome you to 𝐓𝐡𝐞 𝐇𝐢𝐬𝐭𝐨𝐫𝐢𝐜 𝐄𝐬𝐜𝐚𝐩𝐞! Originally The "Louis Johnson Diffee House", located in the popular historic district! 3 BR, 2.5 bath & 3 porches, with the front porch offering a custom daybed swing! Conveniently located and walking distance to many restaurants such as Sweet Old Bills BBQ, Christina Gray’s, & an award winning craft brewery, Brown Truck Brewery! Mins to HPU, HP Market, and the new Rockers Baseball Stadium!

Superhost

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.

Apartment in Winston-Salem

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!

4.98 out of 5 average rating, 171 reviews

A single-story ranch house with a welcoming front porch. Surrounding greenery includes mature trees and well-maintained shrubs. A spacious lawn is visible, providing a serene outdoor environment. A car is parked in the driveway, indicating easy access to the home.

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.

A modern dining area features a circular rug and a wooden table surrounded by six brown chairs. A large light fixture hangs above, complementing the blue walls and natural light flowing through the white-framed windows. Two pairs of French doors separate the space from a living area.

5 out of 5 average rating, 31 reviews

High Point's Gem! Group Friendly! Five Bedrooms!

This stunning 5 bedroom home was designed for gatherings! Whether traveling with family, friends, or on business, your group will love the ability to spread out & enjoy multiple seating and hangout areas plus a fenced-in backyard for the pups! 2 King & 1 Queen bedroom are located on the main level, plus 1 Queen & 1 Twins bedroom upstairs with a cozy loft. Our central location means you'll have easy access to both High Point & Greensboro businesses, attractions, and venues!