Vacation rentals in Jackson Springs

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.

Walk to Village |Heated Pool·Hot Tub·Putting Green

The Enchanted Escape feels like discovering a place someone forgot to tell everyone else about. Tucked on a private acre steps from Pinehurst Village, 3 distinct residences surround a 51-foot heated pool, putting green, hot tub and fire pit. Beyond the backyard, more than a century of character unfolds through stained glass, reclaimed doors, old stone and collected treasures. It’s private, wonderfully quirky and full of little details that keep making people say, “Wait...come look at this.”

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.

Lakeview Landing - 2 BD 2 BA Pinehurst Condo

**Pool OPEN for the season** Welcome to Lakeview Landing, located in the heart of Pinehurst golf! With a second story view of Lake Pinehurst, guests can relax on the balcony or enjoy the community pool! This quiet neighborhood shares close proximity to several great golf courses and has easy access to the BEST parts of Pinehurst: historic downtown, Fair Barn + Harness Track, Pinehurst Resort + Clubhouse, etc. Plus, it's a quick drive to nearby Southern Pines + Aberdeen!

Historic 5 bedroom cottage walk to village & golf!

This beautifully renovated historic home is located in the Village of Pinehurst and is close to shops, restaurants, golf and parks. Built in 1924 as one of the original Leonard Tufts cottages, the home offers an updated kitchen, bathrooms, spacious living areas, four bedrooms, a game room, a large private fenced-in backyard, and more. Dundee Cottage offers plenty of space for families, friends, and golfers to relax and enjoy beautiful Pinehurst.

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.

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.

Isle of the Pines! 1 mi. from Village of Pinehurst

Isle of the Pines is a family owned home with lots of thought put into the experience we want to offer our guests. We pride ourselves on the inviting space we provide through offering luxury amenities such as a fully equipped kitchen, abundantly stocked coffee bar, toiletries upon arrival, several family oriented games, and so much more!. We want you to feel like you have walked into your home away from home!

Quiet Condo on Golf Course near Pinehurst-EV Plug

Featuring 18th Fairway views on the Foxfire Resort and Golf Club, this condo offers a peaceful escape for anyone. This unit is located across the parking lot from brand new Pickleball Courts and the Swimming Pool. Just 10 minutes away from historic Pinehurst Village and Southern Pines, NC. There is a 220 Stage 2 EV plug available that can charge approximately 40 miles per hour.