Guesthouse holiday rentals in Southern Pines

5 out of 5 average rating, 71 reviews

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. Atch. to the main house but fully soundproofed w/ a double wall, 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

Superhost

4.84 out of 5 average rating, 262 reviews

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

5 out of 5 average rating, 41 reviews

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.

4.9 out of 5 average rating, 10 reviews

Adorable 1 bedroom guest house in Southern Pines

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!

5 out of 5 average rating, 9 reviews

Horse Farm Guesthouse

Enjoy the expansive views from all sides of the lovely guest house on Coyote Crosse Farm. Situated above a 3 car garage, you will find a spacious yet cozy oasis. The large primary bedroom has a queen bed and single daybed, and the second tiny bedroom has a double bed. The larger sofa is a queen pullout. Meet the horses and friendly dog, Ripley. Hike in the adjacent Walthour Moss foundation, take a walk to downtown Southern Pines, or visit the nearby Village of Pinehurst for a round of golf!

4.98 out of 5 average rating, 52 reviews

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.

4.92 out of 5 average rating, 63 reviews

Bungalow at the Lake

Private guesthouse bungalow with lake access, on the property. 7 minutes from downtown Southern Pines. 15 minutes from Pinehurst Country Club. Apartment over garage with separate, private entrance and lots of parking space! Kitchenette with fridge and Keurig coffee maker, King size adjustable bed, large TV, private bathroom, and WiFi! Back yard amenities include fire pit, private dock, deck space, and lake access + kayak! Hosts on site and available for any issues during your stay.

4.98 out of 5 average rating, 252 reviews

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.

4.92 out of 5 average rating, 209 reviews

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.

Guesthouse in Downtown Southern Pines

4.95 out of 5 average rating, 534 reviews

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.

Guesthouse in Downtown Southern Pines

4.94 out of 5 average rating, 17 reviews

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.