Holiday rentals in Jackson Springs

Family Fun, Pool, Hot Tub, Sauna, ZipLine, 3King B

Have fun, relax & stay with the whole family at our peaceful, unique home. This is a wonderful neighborhood, mostly quiet. Located out of city limits, but 5 miles to Pinehurst Golf Resort. Occasionally you may hear neighbors practice shooting on their range. We offer many amenities for nearly everyone to enjoy. Walking path, ping pong, pool table, fuseball, darts, volleyball, lrg fire pit, basketball ball, playground, twirly slide, tetherball, pool, playground, Sauna, hot tub & 500 ft Zip line.

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.

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.

A Cozy Retreat on No. 5

Across from the Harness Track and an easy walk to the main clubhouse at Pinehurst sits our villa on the 2nd hole of the Ellis Maples designed Pinehurst No. 5. Our newly renovated 2nd floor unit has 3 bedrooms, 2 bathrooms and and open floor plan. With seating for 8 and 5 beds, you can bring the whole family comfortably. Cook dinner in the kitchen equipped with new stainless and enjoy a glass of wine out of the cooler. This unit has two porches, and both are great for your morning coffee.

Apartment at Working Horse Farm

Bring your horses! Located in Moore County minutes from Pinehurst Golf Courses, the Walthour-Moss Foundation, and the Carolina Horse Park. The Tempest Suite is a private studio apartment with full kitchen and outdoor seating area on our beautiful 14 acre horse farm. Up to two stalls with access to paddock, feed, tack, and wash rooms available for an additional fee. Two RV hookups with power and water available in addition to or separate. Relax with a pint or glass around the fire pit.

Lakeside Escape - 5 Miles from Pinehurst Resort

5 miles from the Pinehurst Resort - Escape to a Lakeside Retreat - where comfort and adventure collide! This 4-bedroom gem sleeps 10 and boasts a cozy gas fireplace, big-screen TV, and free weight gym for staying active. Relax by the pool, paddle across the lake, or fish from the private beach. End your day by one of 3 outdoor fireplaces. With kayaks, a paddle boat and comfortable accommodations, fun and rest are endless. Perfect for unwinding or making memories—your retreat awaits!

The Foxfire Estate

This impressive 6‑bedroom sanctuary is perfect for group retreats! Designed so everyone has their own slice of luxury - whether you're traveling with family, friends, or a special group, the Foxfire Estate is the perfect blend of comfort and elegance. Each bedroom offers its own private en-suite bathroom, creating a luxurious, hotel‑like experience. With stunning views of the private pool and golf course, every detail of this home is designed to create an unforgettable experience.

The Ultimate Golf Trip House - Pool & Pickleball

Escape to Foxfire in the Pinehurst area enjoy a luxury lakefront estate for large groups and unforgettable stays. With a pool (May to Mid-Sept), hot tub, sauna, cold plunge, golf simulator, game room, pickleball/basketball court, and 2 full kitchens, there’s something for everyone. Sleeping up to 24 guests across 12 beds, this retreat features putting greens, fire pit, outdoor pizza oven, and multiple decks overlooking the lake--perfect for relaxing and making memories.

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.

The Patriot - A Ground Floor Condo

Welcome to The Patriot, a beautifully decorated ground-floor condo on the golf course of Foxfire village. Enjoy stunning views of the 17th green, two private decks, tasteful décor, and two en suite bedrooms with king and queen memory foam beds. A dedicated workstation and inviting living space make it easy to work or unwind. Steps from pickleball courts and minutes from Pinehurst, it’s perfect for golfers, couples, and peaceful getaways.

6BR w/ Golf Sim Putting Green Hot Tub Sauna Games

⛳️ The Putting Green is here! ⛳️ This is the Perfect Pinehurst Getaway for golfers, families, and big groups alike! Packed with amenities like a relaxation center including a hot tub, sauna, fire pit! And a world class game room with Uneekor golf simulator, foosball, darts, and Golden Tee! Ask about our golf cart rentals and private chef! 8 min drive to Pinehurst Resort 19 min drive to downtown Southern 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.