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 · Hospitality

The Carriage House on Connecticut.

We are excited to bring you our historic carriage house nestled on the 15th Fairway of MidPines Golf course. Built in 1922 by MAJ D. B. Nettleton, dentist and WW1 veteran from Pittsburgh. The Carriage House has two queen bedrooms, a master, with a large wall mounted TV, sliding Barn door. The second, an ensuite space with a large wall mounted TV, sitting area & large couch. Also included, a full kitchen and Bathroom. Quiet gated property minutes to downtown restaurants and local golf courses.

Location · Check-in · Accuracy

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

Location · Family · Amenities

The Kensington Cottage

Relax and unwind in our newly-renovated cottage, just a short walk from downtown Southern Pines! Spend the day admiring the beauty of the local trails and Sandhill Horticultural Gardens, or explore the quaint "SoPi" shops and Sunrise Theater. Only a ten minute drive to Pinehurst, the area boasts some of the nation's best golfing and a fabulous restaurant scene. The cottage features a new Nectar queen mattress, fast WiFi, an oversized shower, a modern kitchen, and a private yard with fire pit.

Location · Value · Comfort

Haven in The Pines

Welcome to our Haven in the Pines. This space is a welcoming, peaceful retreat. We designed it with the traveler in mind, complete with a king-sized Tempur-Pedic mattress. Experience tranquility and luxurious amenities in this beautiful studio apartment, surrounded by the iconic pines. Just 8 minutes away from downtown and 20 minutes from world class equestrian centers and golf courses, you are never too far from the bountiful activities Moore County has to offer. We hope you enjoy your stay!

Value · Location · Quiet

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 · Hiking

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.

Location · Family · Check-in

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 · Air conditioning

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

Value · Family · Access

French Country Cottage - Walk to Village

French Country cottage comfort and convenience of home in the historic Village of Pinehurst. This property is perfect for a romantic getaway or golf weekend for two. Recently renovated guest house with one room studio and bath with private entrance and parking, kitchenette, walk-in shower. Walk to village for dining, shopping or enjoy morning or evening walks along famed Pinehurst #2 to golf club. All the comforts of home in this quaint European style cottage.

Value · Location · Kitchen

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 · Value · Backyard

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.

Value · Location · Decor