Vacation rentals in Whispering Pines

The Bookery - Bright, Airy home with Fenced Yard

Relax in our bright, 2500+ sqft home on nearly 3/4 of an acre with a large fenced back yard. Pet friendly wood floors throughout, and great spaces for quality time. 1 mile to downtown and only 6 miles to Pinehurst Golf Resort and 13 miles to Carolin Horse Park. Enjoy the sunroom, fully stocked kitchen with gas stove and double oven, the gorgeous patio, or the inviting couch to watch a movie with the whole family! Available for short term leases as well. Looking forward to hosting you and yours!

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.

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.

The 19th Hole- a Pinehurst retreat for golf lovers

Just 5 minutes from Pinehurst Village and world class golfing, this spacious home offers the perfect place to relax. Pinehurst Resort, Mid Pines Golf Club, Pinehurst #2, Southern Pines and three breweries are all less than 10 minutes away. Enjoy outdoor dining, fire pit and yard games. If you are traveling with children, the home can accommodate 2 additional people in twin trundle beds and a toddler on fold out bed in master bedroom. 25% discount for weekly stays.

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.

Cozy Cottage - pet friendly, great location!

Enjoy a cozy and premium experience at this centrally-located place. Two minute drive to the Southern Pines downtown area, 15 minutes to Pinehurst, and just minutes from horse country. We have everything you need to have your dream stay in the Pines. Tons of amenities including: Fenced in backyard Outdoor patio with fire pit and grill Wood fireplace Smart TV Washer and dryer Desk workspace Fast WiFi Smart Thermostats 2 car driveway Full kitchen …and more!

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!

Pinehurst Chatham House| 3BR Near Golf and Village

Escape to Pinehurst in this charming 3-bedroom, 2-bath home, perfect for golfers, families, and weekend getaways. Located minutes from world-famous golf courses, dining, and local attractions, this comfortable retreat offers spacious living areas, a fully equipped kitchen, and relaxing outdoor space. Whether you’re here for a golf trip or family vacation, you’ll feel right at home. Book your stay and enjoy the best of Pinehurst in comfort and style!

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

Ivy Kirk Cottage in the Village of Pinehurst

Kick back and relax in this updated, cozy cottage. When you aren't out on the golf course, take a stroll through the Historic Village of Pinehurst and enjoy the shops, restaurants, and bars. Or walk across the street to the Carolina Hotel and enjoy a meal at the Carolina Vista while watching the sunset from their sprawling veranda. A stay at the Ivy Kirk Cottage is sure to provide you with a vacation to remember.

The Lodge at CaroKen, private and peaceful

Private cabin on 47 acre parcel with pond and firepit. Amazing four sided fireplace in great room. Modern kitchen, large fridge, gas stove. Miles of trails for exploring. Four bedrooms, Two baths. Within 15 minutes of Pinehurst. Great for golf groups. Great place to watch wildlife. Unique historic property.