Holiday rentals in Whispering Pines

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.

Lakeside 10 miles to Tobacco Rd.

Lakeside house on 30 acres, surrounded by trees and privacy. Wraparound porch. 5-person hot tub. Fire pit. Cornhole on the porch. Wooded walking trails. Central to everything without being near anyone. Golf all day; relax or play all night. Convenient to Pinehurst, S. Pines, Sanford & more! Key distances (miles): Quail Ridge: 9.4 Hyland Golf Club: 9.7 Tobacco Rd: 10.1 Downtown S. Pines: 13.2 Moore County Airport: 13.4 Pinehurst No. 2: 17.6 Ft. Liberty: 25.6 RDU Airport: 59.5

Luxury Stay by Pinehurst No. 2- Where Legends Play

🌿 Welcome to Your Pinehurst Retreat Your family will be close to everything when you stay at this centrally-located home in the heart of Moore County. Whether you’re here for golf, local charm, or just a peaceful getaway, you’ll love the comfort, convenience, and Southern hospitality that make this spot so special. Our home is designed with families and friends in mind — cozy, inviting, and fully equipped for your stay. It’s the perfect blend of small-town comfort and modern convenience.

Lakefront | Elite Gym + Spa Bath Near Pinehurst

Lakefront retreat near Pinehurst with private gym, spa-inspired bath & newly added kitchenette—perfect for relaxing, recharging, or staying dialed in while you travel. Tucked inside a quiet gated golf community ~25 minutes from Pinehurst Resort, this private suite is ideal for couples, golf trips, and TDY stays. Enjoy a serene patio overlooking the water, luxury bath experience & exclusive use of a fully equipped professional-grade gym, all within ~20 minutes of Southern Pines + Fort Bragg.

The Road Less Traveled Lake Lodge

Welcome to The Road Less Traveled Lake Lodge, a private lakefront retreat tucked under the pines. The final stretch of road may feel like the road less traveled… and that’s exactly the point. What awaits you is complete privacy, wide water views, and a rare sense of serenity. Mornings begin with coffee on the screened porch. Afternoons are for paddling around the lake. Evenings feel like a true escape. Warm wood ceilings, lodge-style interiors, and uninterrupted sunsets across the lake.

Pinehurst Golf Retreat | Putting Green + 3BR

Enjoy the best of Pinehurst from our recently remodeled 3-bedroom home in family-friendly Village Acres. Less than 2 miles from the Village of Pinehurst, you'll be close to shops, restaurants, parks, Greenway trails, and world-renowned golf. Relax in the spacious fenced backyard and enjoy your own private putting green. Whether you're visiting for golf, a tournament, wedding, family trip, or weekend getaway, you'll have a comfortable home base close to everything Pinehurst has to offer.

Serene By the Greens

Relax in this peaceful, newly renovated space with a modern touch. Located in a quiet neighborhood next to Hyland Golf Club, this home offers the perfect retreat for golf lovers. Just one exit north of Pine Needles golf course (3.9 miles), it’s ideally situated for those attending the US Kids Golf World Championship at Longleaf Golf Club (5.9 miles away) or the US Men’s Open at Pinehurst #2 (8.9 miles away). Secure your golf getaway now—book today!

Farm Retreat near Southern Pines & Pinehurst

Wake up in the heart of North Carolina horse country, surrounded by grazing horses and peaceful pasture views on a working equestrian farm just minutes from Pinehurst and Southern Pines. 10 min to downtown Southern Pines 12 min to Pinehurst golf courses 12 min to Woodlake Country Club Ideal for Pinehurst golf trips, equestrian events, or Fort Bragg visits. Enjoy true Sandhills living with fast Wi-Fi, self check-in, and full comfort.

Welcome to Backyard Retreat!

Welcome to Backyard Retreat. Relax in this cozy, lower-level living area with private entrance. Whether you decide to kick back around the fire pit, take a nap in a hammock or throw down with one of our family friendly board games, we're sure you'll find everything you need for a comfortable stay. BR is an easy 10-minute commute to Southern Pines and Vass 12 minutes to Pinehurst 3.2 miles to Country Club of Whispering Pines

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.

Boutique-Style Pet-Friendly Horse Farm | Fox Den

Experience the Fox Den Suite at Tanglewood Farm—a boutique-style, pet-friendly apartment on a peaceful 10-acre horse farm. This thoughtfully designed one-bedroom retreat features a king bed, cozy living space, and a fully equipped kitchen for a relaxing countryside stay. Just minutes from Southern Pines, Pinehurst, and Whispering Pines, you’re close to breweries, restaurants, boutique shops, and world-class golf.

Good Times in the Pines

If you're visiting the Pines area for golf, equestrian events, dining, shopping, or strolling through the historical villages, this is the place to stay. Our newly renovated condo in Sothern Pines is meticulously clean and has many kitchen amenities. Pets are welcome with no additional fee. We even have a putting green on the back screened in porch.