House holiday rentals in Whispering Pines

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, 178 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.

5.0 out of 5 average rating, 134 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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Guest favourite

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.

4.97 out of 5 average rating, 156 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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A modern farmhouse is presented, featuring a welcoming white exterior paired with natural stone accents. Large windows enhance the exterior, and a covered porch with a railing invites relaxation. Lush green landscaping surrounds the house, offering a peaceful and spacious setting.

4.99 out of 5 average rating, 114 reviews

5 BR ModernNew Build - 5 mins to Golf w/ Game Room

Located in Village Acres, just 1 mile from Pinehurst Resort, this brand-new home is a one-of-a-kind experience. This family-friendly home is equipped with everything you could need to enjoy all that Pinehurst has to offer. -5 Bedrooms, 3.5 baths, 8 total beds (2 king beds) -Dogs are welcome! -5 TVs in the house -High-speed WiFi -Keyless entry -Fully equipped state of the art kitchen -Complimentary coffee -Ping Pong Table -Poker Table -Travel Crib -Weber BBQ Grill - Work space

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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, 136 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, 128 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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Guest favourite

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, 241 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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Guest favourite

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, 144 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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An open living and dining area features high, vaulted ceilings supported by wooden beams. A brick fireplace is centered on the wall, accompanied by cozy seating arrangements on a plush area rug. A dining table is set with decorative accents, and large windows offer natural light.

4.98 out of 5 average rating, 104 reviews

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.

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4.98 out of 5 average rating, 121 reviews

Cozy, private and CLEAN @ The Abbey.

This is a private in-law suite with private entrance. There are no shared spaces. Private bath, pet friendly (*Fee). We have taken extra precautions to sanitize, and clean this space. If you are a medical professional here for work, please let us know. We are less than a mile from the hospital and would be happy to have you. Our place has been cleaned and sanitized from top to bottom.

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