Guesthouse holiday rentals in Southern Pines

Storybook Tree House- 2 Mins to Local Breweries!

This space is perfect for the romantic couple getaway or a small group exploring Southern Pines! While rustic, we are located right near downtown, just a short distance (< 1mi) from restaurants, breweries, and cafes. We offer 𝙵̲𝚁̲𝙴̲𝙴̲ ✓Coffee and tea ✓Water and soda ✓Wifi ✓Mini fridge ✓Smart TV ✓Doggy bowls ✓Firewood ✓Fire pit ✓Extra blankets and towels ✓Self check in The property is shared with a single family home that is also available for rent here: https://airbnbcom/h/staypinehurst

Family · Location · Sleep quality

Charming 1 bedroom guesthouse on 4 acres, hot tub

Our guesthouse sits on 4 quiet fenced acres about 100 feet from our home. We are about 15 minutes from Pinehurst. Our large, friendly dogs greet you upon arrival and share the same fenced area as the guesthouse. Our barn conversion has a full kitchen, a queen bed and small sofa bed. Coffee maker, wine fridge, fire pit with Adirondack chairs for evening glass of wine or to watch the fireflies. Saltwater pool from mid-May to Mid- Sep. Private two-person hot tub. Pet fee for dogs. sorry, no cats.

Family · Value · Wi-Fi

Peaceful retreat in the pines

Enjoy relaxing on the back deck in the trees after a long day of horse showing or several rounds of golf. 3 minutes to downtown Southern Pines eat dessert 1st at Ashtons or travel down the way to Pinehurst. This private charming apartment is lovely for enjoying all that the area has to offer. Soaking tub, kitchenette, office space and a big comfy bed. 18 minutes to the Carolina Horse Park, 3 minutes to downtown Southern Pines and 15 minutes to downtown Pinehurst, 6 minutesto downtown Aberdeen

Family · Location · Indoor spaces

Cozy Guest Studio | Prime Location | dog friendly!

The Blackwell Lodge is a unique place has a style all its own. Need a space to stay close to downtown Southern Pines and the Pinehurst area? Keep it simple at this peaceful and centrally-located guest house. One bedroom efficiency featuring full size washer and dryer, full bath, mini Kitchenette with a sink, induction cook top, Microwave, and mini fridge. Desk. Enjoy walking downtown and bikes for guests to use as well. This guest house is stylish and beautifully decorated for your stay!

Family · Location · Walkability

Charming Getaway Carriage House with pool

Welcome to our peaceful guesthouse in Southern Pines, NC! This contemporary retreat offers a serene escape with a pool, charming gazebo, and stunning views of the championship golf course, Pine Needles. The spacious unit is decorated in a modern style, providing a comfortable and inviting ambiance. Relax poolside or take a stroll through the well-manicured grounds. Golf enthusiasts will delight in the proximity to the renowned course. Discover tranquility and luxury in this hidden gem.

Family · Location · Shared spaces

Historic Southern Pines Carriage House

Just minutes from Pinehurst and only one mile from downtown Southern Pines, this Tudor Revival Carriage House keeps you close to golf and activities! Enjoy a peaceful setting surrounded by an acre of Longleaf Pines, Camellias & Azaleas. Enjoy a full kitchen (refrigerator, no freezer), private bath with tub/shower. Enjoy area golf courses or stop in when visiting Penick Village, the Carolina Horse Park or Ft. Liberty. Please NO PETS, NO SMOKING/VAPING inside, NO PARTIES.

Family · Location · Condition

Mystical Cottage

A warm cozy guest house with an open floor plan, high ceilings, and a wall of glass doors overlooking the pool and jungle like backyard of 3 acres. It has a large separate bath and complete kitchen. It was a perfect place for a completely secluded getaway ... less than 2.5 miles from the center of both Southern Pines and the Village of Pinehurst... 8 minutes from nearly every restaurant in the area. We are pet friendly, but charge a seperate $35 pet cleaning pet.

Location · Family · Bathroom

Quiet and Safe neighborhood Studio for 2

Enjoy a peaceful stay in this fully furnished studio for two, located in a quiet Southern Pines neighborhood. Separate unit behind the main home, it offers a private key code entrance, queen bed, and a kitchenette w/ a hot plate and griddle. Step outside to your own private area with a fire pit. Just minutes from shopping, restaurants, breweries, golf courses, and movies. Only 15mins to the hospital, 20mins to Rockingham Racetrack, and 9mins to the Walthour Moss Fdtn

Family · Value · Getting around

Quaint Cottage Refuge in Historic Downtown

LITERALLY steps from the quaint downtown of Southern Pines. In the heart of the historic district of Southern Pines sits this cozy eclectic 1930's cottage. Guests will have the entire cottage for their private use. This cottage is filled with unique & eclectic furnishings. Come, stay and enjoy! Spend time on the private screened in porch. Grab a book and relax in the hammock. Central HVAC 1 bed / 1 bath / 1 sofa bed Strict 'No Pet' policy.

Location · Family · Shared spaces

Carthage Country Guesthouse

This is a peaceful area with time to just slow down a little. Looking for a little peace & quiet? I have the place for you. Very cute Guesthouse nestled deep in the country area of Carthage. It's like taking a few steps back in time when life was simple. We are located within minutes to Pinehurst, Seven Lakes, Cameron, Pottery Highway and downtown Carthage. A very quiet area with nothing but the sounds of Mother Nature.

Value · Family · Comfort

The Pinecone Carriage House

Nestled just minutes from Pinehurst and a mere block from downtown Southern Pines, the Pinecone Carriage House offers a perfect blend of convenience and comfort. The house itself, though unassuming, surprises with its cozy simplicity. Every detail has been thoughtfully curated to ensure a fantastic stay. Whether you’re here for golf, exploring the town, or simply unwinding, this house promises a memorable retreat.

Value · Family · Check-in

The Cottage at Knollwood Manor

Relax at The Cottage, a private getaway situated on the Knollwood Manor estate next to the 15th Fairway of Mid Pines Golf Course. This quaint and cozy cottage is stocked with all of the necessities and conveniences to relax in The Pines and is situated at the ideal location for easy access to all local attractions.

Location · Value · Amenities