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A Cozy Retreat on No. 5

Across from the Harness Track and an easy walk to the main clubhouse at Pinehurst sits our villa on the 2nd hole of the Ellis Maples designed Pinehurst No. 5. Our newly renovated 2nd floor unit has 3 bedrooms, 2 bathrooms and and open floor plan. With seating for 8 and 5 beds, you can bring the whole family comfortably. Cook dinner in the kitchen equipped with new stainless and enjoy a glass of wine out of the cooler. This unit has two porches, and both are great for your morning coffee.

Hot Tub * King Bed * Putting Green * Amazing Golf

Welcome to The Stay and Play Retreat! We’re centrally located minutes away from some of the areas greatest attractions such as Pinehurst No. 2 (8 Miles), Rockingham Dragway (14 miles), Carolina Horse Park (10 miles), and Fort Bragg (16 miles) . We're also surrounded by many beautiful golf courses including Legacy Golf Links and a wide variety of dining options within 11 miles of this completely renovated home that has been created specifically for your comfort, relaxation & enjoyment.

Loft Cottage on Ridge Short & Extended Stays

This 1930s cottage is the perfect spot for your stay in downtown Southern Pines. It is located on a quiet street, yet close enough to walk to all the shops/restaurants downtown or the Weymouth Center for the Humanities. This loft unit has a private entrance from the top of the stairs with 1 bedroom (Queen) & 1 bath, a full kitchen, and shared laundry room downstairs in the back of the home. Unit features vintage kitchen! Come stay with us for a short stay or extended stay!

Lakeside Cottage nestled near Pinehurst and CHP

Bellago Farm Cottage is nestled in the woods off the edge of the North Carolina Game Lands. It is 6 miles from the Carolina Hotel/Pinehurst Resort and the famous Pinehurst #2 Golf Course, and 8 miles from the Carolina Horse Park. The lakeside cottage welcomes you to fishing and swimming its spring-fed 9-acre, very clear waters. Enjoy relaxing between activities with easy access wi-fi or tv. If you are traveling to the area for equine competition, horse boarding is available.

Old Blue's Retreat: Lakeview Cozy Cottage

Old Blue’s Retreat is minutes from Pinehurst & Southern Pines, NC. While the lake has been temporarily drained due to damage from tropical storm, Chantal, the property remains peaceful and inviting with wide-open views, abundant wildlife, and sunsets to remember. The cottage is furnished with charm to spare and offers 3 bedrooms, 2 baths, a full kitchen, spacious living area, and sunroom. Enjoy the sauna, fire pit, private dock, and easy access to golf, dining, and shopping.

Lakeview Landing - 2 BD 2 BA Pinehurst Condo

**Pool CLOSED for the season** Welcome to Lakeview Landing, located in the heart of Pinehurst golf! With a second story view of Lake Pinehurst, guests can relax on the balcony or enjoy the community pool! This quiet neighborhood shares close proximity to several great golf courses and has easy access to the BEST parts of Pinehurst: historic downtown, Fair Barn + Harness Track, Pinehurst Resort + Clubhouse, etc. Plus, it's a quick drive to nearby Southern Pines + Aberdeen!

Entire Condo · Greenview Retreat · Walk to PCC

Beautiful 1BR/1BA retreat in Pinehurst with stunning Course #5 views. Enjoy full access to the entire condo with complete privacy—your bucket-list destination and home to the US Open. Perfect for couples, golfers, or medical professionals. Walk to Pinehurst Country Club, and stay close to shops and hospitals (first health of the Carolinas). Fully equipped with fast Wi-Fi, New TV, dedicated workspace, and in-unit laundry. Long-term stays welcome, with discounts available.

The Knotty But Nice Treehouse of Pinehurst

Welcome to The Knotty But Nice Treehouse of Pinehurst. If you're looking for a rental experience in Pinehurst that is unique -- look no further! Our one of a kind treehouse is nestled between Lake Pinehurst and The No. 3 Course. Located just minutes from the village of Pinehurst and the Pinehurst Resort. Past guests describe The Knotty But Nice Treehouse as CLEAN, COZY, ROMANTIC, BEAUTIFUL, UNIQUE, PEACEFUL... Go ahead and book-- you won't be disappointed.

Water Oaks Cottage - Near Pinehurst Country Club

Three blocks by foot, bicycle or golf cart from the Carolina Hotel, deemed in 1901 the “Queen of South”, with its fine dining, entertainment, highly acclaimed “Spa at Pinehurst”, restaurants and shops of Pinehurst Village. Straight down from this grand resort by lovely promenade is the world-famous Pinehurst Country Club and renown “Number 2” championship golf course. A few blocks further, the 111 acre equestrian facility and historic Pinehurst Harness Track.

Peaceful Horse Farm Retreat

Perfect for a getaway! Anahata Farm Retreat is nestled in the midst of Southern Pines' horse country, one hour south of Raleigh. We are located near the end of a quiet, private dirt road. There is space to roam and animals to greet. This a peaceful, pet-friendly spot, guaranteed to help you relax and reconnect. For more pics, search socials for @anahatafarm. Please do not book this room unless you will be the one staying here. NO SMOKING.

Charming Retreat in Historic Downtown

LITERALLY steps from the quaint downtown of Southern Pines. This charming retreat is unique, eclectic and super cozy! Stay, enjoy and relax in the confines of which used to be a garage. This space features all brick floors, lots of windows with plantation shutters, books, a comfy bed, walk in tiled shower, kitchen and quite distinctive décor. Peruse the large selection of books and enjoy some reading during your stay.

Highland Hideaway/Pool & Fire Pit/$0 Cleaning Fee

Nestled in a peaceful neighborhood just a few miles from downtown Southern Pines and multiple world-renowned golf courses ⛳️ . A 3-bedroom / 2.5-bathroom home with a bonus room. Spacious open porches overlook an inground pool, perfect for those hot summer days, and a fire pit, perfect for relaxing during the evenings. This home is also a short drive to Fort Liberty and surrounding hospitals.