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.

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.

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.

Location is everything !

Location! Cozy efficiency located in the heart of Golf And Horse country! Just 30 seconds 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, and desk area. It is attached to my home so there is daily activity, but we welcome friendly engagement and will respect your privacy.

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!

Delightful Bungalow in Historic Downtown

LITERALLY steps from the quaint downtown of Southern Pines. In the heart of the historic district of Southern Pines sits this charming, quaint & cozy 1930's bungalow. Just steps from our idyllic downtown of Southern Pines. (Literally 1 block!) You will be treated to a private, clean, cozy and updated space filled with everything you will need for a wonderful stay. 1 bedroom / 1 bath / 1 sleeper sofa. Street parking. Strict 'No Pet' policy.

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.

Cardinal’s Nest | Steps from PH #2 & Village

Welcome to Cardinal’s Nest! Your Perfect Pinehurst Getaway! This charming and historic single-level home is nestled in the heart of Old Town Pinehurst. Surrounded by peaceful pines and timeless character, it blends original charm with thoughtful updates for a relaxing stay. You’ll be just a short stroll from Pinehurst No. 2, the Village, world-class golf, local dining, and quaint shops, everything you need for a true Pinehurst experience.

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

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.