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

Location is everything !

Location! Cozy efficiency located in the heart of Golf And Horse country! Just 30 seconds (for real) to the main traffic circle which takes you to great restaurants, shopping, hospital (FirstHealth Moore Regional 1.5 miles away) and, of course, golfing!! The efficiency offers a private entrance, full bed, bathroom w/ shower, kitchenette, desk area, and outdoor seating. It is attached to my home so there is daily activity, but we welcome friendly engagement and will respect your privacy.

A Golf Front SFH 3 BR 2 BA in Pinehurst # 6

A golf front great view 3 BR 2 Bathrooms with furnishings bungalow situated on Pinehurst #6. This house comes with WIFI and 4 smart TVS (Spectrum cable with golf channel). All 4 beds (1 K, 1 Q, 2 double) are with memory foam mattresses. sofa set, dining table for 8, 55'' smart TV on the wall and washer/dryer combination. Enjoy relaxing on the deck after a great round of golf. Amenities include a full kitchen, coffee maker, cookware, microwave, refrigerator.

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!

Cozy Cottage with Sauna. 10 min from Pinehurst

Old Blue’s Retreat — a peaceful escape just minutes from Pinehurst & Southern Pines, NC. Quiet setting with wide-open views, wildlife, and memorable sunsets Lake temporarily drained due to storm damage, but property remains serene and full of wildlife. 3 bedrooms & 2 full baths Fully equipped kitchen, spacious living area, and sunroom. Sauna, fire pit, and private dock. Close to over 40 world-class golf courses, dining, and shopping.

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.

Modern Home | Poker |Golf Simulator | Pet-friendly

WELCOME TO OUR MODERN GOLF RETREAT! Settle into comfort at our stylish 4-bedroom, 2-bath home, can comfortably host up to 10 guests—perfect for families, friends, and fellow golf lovers. Whether you're here to explore Pinehurst, unwind in a cozy space, or enjoy a golf getaway with your crew, we’ve got you covered. And yes, your pup is welcome too—this home is dog-friendly!