Vacation rentals in Whispering Pines

A welcoming entrance to a single-story house is framed by a well-maintained stone walkway and vibrant green landscaping. Windows adorned with white shutters reflect natural light. The garden features varied shrubs and trees, contributing to the tranquil setting.

4.98 out of 5 average rating, 140 reviews

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!

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4.79 out of 5 average rating, 38 reviews

An outdoor area features a stone patio surrounding a sparkling inground pool. Comfortable seating is provided by several lounge chairs and a patio table shaded by an umbrella. A fire pit is positioned centrally, with brick walls enhancing the space and landscaped greenery in the background.

Home in Carthage

Welcome to the Castle, Private Pool spacious

Must be at least 25 to book. Rental Agreement and security deposit required. Additional guest fee over 14 guests No 3rd party bookings. Disclosed pet fee with approval, $500 undisclosed pet fee, $50/hr late check out fee. No one night reservations less, 5 min for holidays. Cancellation Policy 100% (less $100.00 cancellation fee) if cancellation occurs at least 60 days before arrival; No refunds within 60 days of arrival. $500 refundable security deposit required. POOL HEAT AVAILABE NO CHARGE

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A warmly colored dining area is highlighted by a large round table surrounded by eight black leather chairs. Natural light enters through tall arched windows, complementing the rich orange walls and decorative white wainscoting. A classic chandelier hangs above, adding elegance.

4.98 out of 5 average rating, 179 reviews

The Ross Retreat - In Pinehurst

Your entire group will enjoy this central location to 40+ golf courses in Moore county with easy access to restaurants and close to grocery stores. This gorgeous home with custom woodwork and backyard oasis is the perfect retreat for families and golfers alike. Enjoy comfortable beds with down pillows and high end mattresses with mattress pads and a fully stocked kitchen in this newly furnished home. If you appreciate the little things like HEPA air filters and quite dishwashers, we got you.

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The exterior of a two-story cottage is shown, featuring a white clapboard façade with dark roofing. A covered porch is seen at the front, furnished with a small round table and four chairs, surrounded by landscaping with young plants and mulch.

4.99 out of 5 average rating, 138 reviews

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.

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5.0 out of 5 average rating, 5 reviews

Home in Carthage

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.

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A cozy bedroom interior features a queen bed adorned with fresh linens and stacked towels. Natural light enters through a window, illuminating the warm-toned decor and subtle artwork above the headboard.

4.96 out of 5 average rating, 159 reviews

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.

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The exterior of the home features a welcoming facade with a combination of siding and stone accents. A spacious driveway leads to a two-car garage. Two chairs are positioned on the porch, surrounded by landscaped greenery and a fenced yard.

4.98 out of 5 average rating, 138 reviews

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.

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The charming exterior features a welcoming porch with an American flag hanging prominently. Two rocking chairs are positioned invitingly. Lush greenery surrounds the home, and stacked firewood is neatly arranged beside the entrance. A pathway of gravel leads up to the front steps.

5.0 out of 5 average rating, 130 reviews

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!

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4.93 out of 5 average rating, 122 reviews

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.

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The entrance to the home is framed by tall pine trees, showcasing a well-maintained path leading to a welcoming front door. A modern gate and house number are visible, enhancing the overall appeal of the property.

4.97 out of 5 average rating, 242 reviews

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!

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A welcoming entryway features a decorative wreath on a teal door. A console table with a mirrored surface is flanked by two blue and white lamps. Light wood flooring complements the beige walls, leading to an open view of a kitchen area through a doorway.

4.9 out of 5 average rating, 145 reviews

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!

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