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.

Pinehurst 6 Golf Front | 1-Level | 3BR/2BA | 8

A golf front great view 3 BR 2 Bathrooms with furnishings bungalow situated on Pinehurst 6. This house comes with 1GB WIFI, 4 smart TVs with Spectrum cable and Golf Channel, and comfortable memory foam mattresses (1 King, 1 Queen, 2 Doubles). Relax on the deck after golf, enjoy the spacious living area, dining table for 8, and fully equipped kitchen with coffee maker, cookware, microwave, and refrigerator. Washer/dryer included. Perfect for golf trips, family stays, and Pinehurst getaways!

New 5 Bedroom Cottage on Pine Needles Golf Course!

New construction home on the golf course of Pine Needles Course between Pinehurst and downtown Southern Pines. Ideal location, close to everything the area has to offer. This 5 bedroom and 3 bathroom cottage is ideal for golf outings and family friendly vacations. Everything you need to make your stay ideal and comfortable. Main level: 1 bedroom, 1 bath, living room, kitchen, dining, office space, walk in pantry, laundry room. Second floor: 4 bedrooms, 2 bathrooms, abundant closet space.

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

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.

Horse 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. Private apartment only: 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 Liberty visits. Enjoy true Sandhills living with fast Wi-Fi, self check-in, and full comfort.

Golfer's Paradise I Modern I Charming I 3BED/2BATH

Ideal for tournament stays and multi-day golf trips! Centrally located between Pinehurst and Southern Pines Accommodating up to 6 guests in exceptional comfort, our 3-bedroom, 2-bath Charming Pines Hideaway is ideally located within walking distance of Pine Needles Lodge and Golf Club. The great location provides easy access to nearby golf, horseback riding, hiking trails, kayaking, restaurants, and downtown districts of the Pinehurst/Southern Pines area.

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!

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

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.

Lake and Golf View Vacation

Newly redone floors! I look forward to sharing this hidden gem with you! Whether you plan to visit for the golf, horseback riding, or the many other activities that the Sandhills, North Carolina region has to offer, this is the place you want to stay! Located across from the Centennial Pinehurst 8 golf course, I am looking to share this home with those who will love it as much as I do.

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.