Vacation rentals in Jackson Springs

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Top-rated vacation rentals in Jackson Springs

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Top guest favorite

A fire pit surrounded by six wooden chairs is illuminated by a warm fire. The sky above displays streaks of stars, creating a unique celestial backdrop. The area is softly lit, inviting evening gatherings.

Home in Pinebluff

4.99 out of 5 average rating, 176 reviews

Hot Tub * King Bed * Putting Green * Amazing Golf

Welcome to The Stay and Play Retreat! We are centrally located just minutes away from some of the areas greatest attractions such as Pinehurst No. 2 (8 Miles), Rockingham Dragway (14 miles), Carolina Horse Park (10 miles), and Fort Bragg (16 miles) . We're also surrounded by over 20 beautiful golf courses including Legacy Golf Links and a wide variety of dining options within 11 miles of this completely renovated home that has been created specifically for your comfort, relaxation & enjoyment.

Guest favorite

A screened back porch is visible through sliding glass doors, featuring two black chairs positioned for comfort. The view beyond showcases a well-maintained grassy area, framed by trees, offering a peaceful outdoor setting.

Condo in Pinehurst

4.95 out of 5 average rating, 240 reviews

Guest Favorite Condo w/ Golf Views! Clean + Comfy

Welcome to your cozy Pinehurst retreat! Whether you're here for a golf tournament, a quick getaway or a longer stay, this clean, comfy ground-floor condo is a great home base. Enjoy a well-stocked kitchen, inviting furnishings + a screened porch with fairway views - perfect for morning coffee or evening wine! It's very close to the historic Village with shops + dining, plus the fair barn, harness track + Pinehurst resort/clubhouse. With its peaceful, well-located setting, it's a guest favorite!

Top guest favorite

An outdoor seating area is showcased, featuring two armchairs and a matching coffee table. The chairs are equipped with navy cushions, each adorned with decorative blue patterned throw pillows. The setting is complemented by a white wall and a door with geometric designs behind the furniture.

Farm stay in Southern Pines

4.99 out of 5 average rating, 179 reviews

Finally Home Farm Bed and Barn

Bring your horse and your golf clubs! Welcome to Finally Home Farm Bed and Barn! A private 1 bedroom barn converted into a quaint cottage. Located on a peaceful farm just 2 miles from downtown Southern Pines, 1 mile from the back gate of Ft. Bragg and next to Weymouth Woods State Park, Finally Home Farm is the perfect place to explore all the Sandhills has to offer. *We are horse ($40) and dog friendly ($50) pet fee with Pre-Approval. Please include this info in your pre-booking.

Guest favorite

A coffee maker is positioned on a granite countertop adjacent to a decorative paper towel holder. A blank notepad rests nearby, indicating a space for notes or reminders. The setting appears well-organized and functional, reflecting an inviting kitchen area.

Cottage in Pinebluff

4.92 out of 5 average rating, 208 reviews

Lakeside Cottage nestled near Pinehurst and CHP

Bellago Farm Cottage is nestled in the woods off the edge of the North Carolina Game Lands. It is 6 miles from the Carolina Hotel/Pinehurst Resort and the famous Pinehurst #2 Golf Course, and 8 miles from the Carolina Horse Park. The lakeside cottage welcomes you to fishing and swimming its spring-fed 9-acre, very clear waters. Enjoy relaxing between activities with easy access wi-fi or tv. If you are traveling to the area for equine competition, horse boarding is available.

Top guest favorite

The Tudor Revival Carriage House is set amongst tall Longleaf Pines, with warm lighting emanating from its windows. The structure features a gravel driveway, dual garage doors, and is complemented by lush greenery around its perimeter.

Guesthouse in Southern Pines

4.98 out of 5 average rating, 242 reviews

Historic Southern Pines Carriage House

Just minutes from Pinehurst and only one mile from downtown Southern Pines, this Tudor Revival Carriage House keeps you close to golf and activities! Enjoy a peaceful setting surrounded by an acre of Longleaf Pines, Camellias & Azaleas. Enjoy a full kitchen (refrigerator, no freezer), private bath with tub/shower. Enjoy area golf courses or stop in when visiting Penick Village, the Carolina Horse Park or Ft. Liberty. Please NO PETS, NO SMOKING/VAPING inside, NO PARTIES.

Top guest favorite

A dining area is furnished with a table and four chairs, positioned near large windows with wooden blinds. Natural light enters the space, highlighting polished wood floors. A decorative chair adds a touch of elegance, and a writing desk is visible, showcasing brochures and flyers.

Apartment in Pinehurst

4.99 out of 5 average rating, 115 reviews

Upscale 1 BR condo on Pinehurst #3 & #5

Well appointed 2nd floor 1 BR condo nestled within Pinehurst #3 and Pinehurst #5 courses! A short 15 min walk to Pinehurst Village. Main Pinehurst Resort Clubhouse (Pinehurst #2) is a short walk across the fairway and Beulah Hill Rd. Equipped with a full kitchen. Bedroom has a comfortable queen bed and a flat screen TV. Spacious living room with sofa that folds out to a queen bed. 4K Smart TV with easy access to Netflix, Amazon, YouTube & VUDU. Wi-Fi included.

Top guest favorite

A rustic centerpiece is displayed on a table, featuring a tall blue glass vase filled with fluffy cotton branches. An antique-style birdcage and a decorative candle holder rest on a wooden slab, all set against large windows that frame a serene outdoor view.

Home in Pinehurst

4.98 out of 5 average rating, 786 reviews

The Knotty But Nice Treehouse of Pinehurst

Welcome to The Knotty But Nice Treehouse of Pinehurst. If you're looking for a rental experience in Pinehurst that is unique -- look no further! Our one of a kind treehouse is nestled between Lake Pinehurst and The No. 3 Course. Located just minutes from the village of Pinehurst and the Pinehurst Resort. Past guests describe The Knotty But Nice Treehouse as CLEAN, COZY, ROMANTIC, BEAUTIFUL, UNIQUE, PEACEFUL... Go ahead and book-- you won't be disappointed.

Guest favorite

An inviting entrance is showcased, featuring a framed porch with two wooden benches and a lantern overhead. The front door stands open, revealing a glimpse of the interior. A stone pathway leads up to the porch, bordered by greenery.

Cottage in Pinehurst

4.92 out of 5 average rating, 296 reviews

Water Oaks Cottage - Near Pinehurst Country Club

Three blocks by foot, bicycle or golf cart from the Carolina Hotel, deemed in 1901 the “Queen of South”, with its fine dining, entertainment, highly acclaimed “Spa at Pinehurst”, restaurants and shops of Pinehurst Village. Straight down from this grand resort by lovely promenade is the world-famous Pinehurst Country Club and renown “Number 2” championship golf course. A few blocks further, the 111 acre equestrian facility and historic Pinehurst Harness Track.

Top guest favorite

The image showcases a wooden dock leading to a serene lake surrounded by dense greenery. The calm water reflects the overcast sky, with lily pads visible on the surface. Trees line the shore, contributing to the tranquil natural setting.

Guest suite in Southern Pines

4.96 out of 5 average rating, 245 reviews

Golf Resort, Private Entrance, Bath & Kitchenette

This Condo is located on Talamore Golf Resort and is minutes away from many world class golf courses, to include Pinehurst Resort. Approximately 40 minutes to Fort Bragg for Military/DOD civilians who are TDY or house hunting; 4 miles to First Health Moore Regional Hospital for travel nurses; 2.5 miles to Sandhill community college; Reservoir Park is a 250 yard walk from the front door and includes a 95 acre lake, and more than 12 miles of Greenway Trails.

Top guest favorite

The kitchen features white cabinetry and a light countertop, complemented by a subway tile backsplash. Stainless steel appliances are visible, including a coffee maker and a sink with a modern faucet. A tray of snacks and bottled water are neatly arranged on the countertop.

Condo in Pinehurst

4.99 out of 5 average rating, 149 reviews

To The Green On #17 - Studio w/ GREAT Golf Views!

PERFECT LOCATION - only a 5 minute walk to the Pinehurst Golf Clubhouse! "To The Green On #17" is a second-story studio condo perfectly located on hole #17 of Pinehurst No. 3 Golf Course. Relax on the private back deck with open views of the fairway and enjoy the sunshine and unparalleled peace and quiet. Cozy yet luxurious finishes combined with an excellent location make this studio condo perfect for a weekend golf getaway or an extended stay!

Top guest favorite

A modern living area features two plush armchairs flanking a contemporary electric fireplace. A flat-screen TV is mounted on a textured white wall behind the fireplace, which radiates a soothing blue and purple glow. A stylish ottoman occupies the center of the space.

Condo in Pinehurst

4.99 out of 5 average rating, 109 reviews

The Lucky Lie - Entire Condo in Pinehurst

Come relax at the luxurious Lucky Lie! This beautifully renovated studio condo is located just off the beaten path on Pinehurst No. 3, but still perfectly situated for an easy approach into downtown Pinehurst and the surrounding Sandhills. Unwind after your rounds on the porch over looking No. 3, 16th fairway, relax in front of the electric fireplace, or knock out some work in the dedicated workspace, the Lucky Lie has what you're looking for!

Top guest favorite

A charming red guesthouse is framed by lush greenery under a starlit sky. Soft lighting illuminates the entrance, revealing a welcoming porch with steps leading up to it. The surrounding area is tranquil, emphasizing the peacefulness of the countryside.

Guesthouse in Carthage

4.95 out of 5 average rating, 279 reviews

Carthage Country Guesthouse

This is a peaceful area with time to just slow down a little. Looking for a little peace & quiet? I have the place for you. Very cute Guesthouse nestled deep in the country area of Carthage. It's like taking a few steps back in time when life was simple. We are located within minutes to Pinehurst, Seven Lakes, Cameron, Pottery Highway and downtown Carthage. A very quiet area with nothing but the sounds of Mother Nature.