Holiday rentals in Rockingham

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Top-rated holiday rentals in Rockingham

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Guest favourite
The entrance to a charming cottage is framed by lush greenery and well-maintained landscaping. A stone pathway leads to the front door, while a gravel driveway guides visitors through vibrant shrubs and trees.
Cottage in Southern Pines
4.96 out of 5 average rating, 378 reviews

The Ace Cottage - Tiny-home Feel, Close to golf

Unwind in the privacy of this adorable tiny-home! Just over a mile from downtown Southern Pines and less than 15 min to the famous Pinehurst Resort. Features a King size Nectar bed, Fire TV, WiFi, shower with tankless water heater a bistro set, and a Kitchenette (sink, dishes, Keurig, microwave, mini fridge w/ freezer, toaster oven, and electric skillet), beautiful stone patio, professional landscaping, pet yard access, brand new floors, and a large driveway. The perfect spot for a quiet night!

Guest favourite
A modern kitchen features sleek cabinetry and stainless steel appliances, including a microwave and oven. A textured wooden countertop complements the design. A small dining table with green chairs is visible, alongside a window adorned with sheer curtains, allowing natural light to brighten the space.
Flat in Hamlet
4.96 out of 5 average rating, 27 reviews

Stylish Apartment Near Downtown

Relax in this peaceful one bedroom apartment near the quaint downtown Hamlet Main St and train station. This is a great place for travelers, traveling nurses, and business/work visits. It is in close proximity to Rockingham/Pinehurst/Cheraw/Laurinburg for your golf, disc golf, shopping, work and racing at "The Rock" interests. The apartment is located in a 1950s home that has been split into three separate apartments. Each apartment has its own private entrance and exit. No spaces are shared.

Top guest favourite
A soothing hot tub is illuminated by soft blue lights, creating a calming ambiance. The surrounding area features a modern privacy screen, subtly highlighted by exterior lighting, enhancing the serene nighttime setting.
Home in Pinebluff
4.99 out of 5 average rating, 199 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 many 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 favourite
A dining area features a wooden table surrounded by four chairs, set against a white brick wall with decorative letters spelling 'EAT.' Built-in cabinetry and a small wine cooler are present, contributing to the open and bright space illuminated by natural light from the window.
Villa in Pinehurst
4.95 out of 5 average rating, 127 reviews

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.

Top guest favourite
A charming brick structure features a peaked roof and three garage bays with decorative trim. The landscaped area includes trimmed hedges and blooming flowers in a planter. Trees can be seen in the background, creating a serene outdoor setting.
Flat in Laurinburg
4.98 out of 5 average rating, 504 reviews

Chauffeur’s Apartment on Historic Property

Enjoy the former chauffeur's quarters located on the grounds of our National Register of Historic Places property with access to the tranquil gardens of the Manor House. The kitchen is complete and the comfortable full-sized bed should provide a good night's rest. Downtown activities are within easy walking distance. There are multiple seating areas to enjoy the extensive gardens on the one acre grounds that are shared with the main property. We cannot host guests under the age of 16.

Guest favourite
A two-story gray building is shown, featuring a welcoming front porch with white railings. Flanking staircases lead to the upper level, and two sets of double doors are visible on the ground floor. Lush green grass surrounds the structure under a partly cloudy sky.
Flat in Town of Rockingham
4.92 out of 5 average rating, 25 reviews

Skipper 1

Be one of the first to stay in our newly renovated apartments designed for comfort and style! Whether you’re here for business, a temporary stay, or visiting family, you’ll feel right at home. Centrally located near Rockingham Motor Speedway, Hwy 74, Route 1, dining, shopping, hospitals, and more. Plus, we’ve got your peace of mind covered with on-site video surveillance and private parking. Up to 4 units are available to rent simultaneously for larger group or room needs.

Top guest favourite
A spacious living area features a large L-shaped sectional sofa in soft brown fabric, arranged on a patterned area rug with floral designs. A ceiling fan hangs above, and the adjoining kitchen can be seen in the background, equipped with dark wooden cabinets and stainless steel appliances.
Cottage in Pinebluff
4.92 out of 5 average rating, 226 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 favourite
Home in Pinehurst
4.98 out of 5 average rating, 817 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.

Top guest favourite
A spacious studio is illuminated by natural light, featuring two large beds with plush bedding. A comfortable seating area is positioned near a window, with views of the lush outdoors. Modern furnishings and a breakfast bar complement the inviting layout of the space.
Apartment in Pinehurst
4.99 out of 5 average rating, 127 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 favourite
A quaint red guesthouse is observed, featuring a covered entryway with steps leading to the porch. Surrounding greenery is present, highlighted by a large tree in the foreground. The property is set in a natural environment, suggesting tranquility.
Guest house in Carthage
4.95 out of 5 average rating, 287 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.

Guest favourite
A bright living space is presented with a gray couch adorned with yellow cushions, accompanied by a round wooden dining table with black chairs. Natural light streams in through large windows, with decorative elements such as woven wall art and a potted plant adding a touch of warmth.
Apartment in Pinehurst
4.94 out of 5 average rating, 284 reviews

Fairway to Heaven - 2BD 2BA Golf Front Condo

Welcome to Fairway to Heaven, located within walking distance of the Pinehurst clubhouse and Village of Pinehurst! With a second story view on the Pinehurst #3 course, guests can enjoy hours of relaxation on the balcony overlooking the fairway, or stroll down to the historic Village for a cocktail, dinner or shopping. A 5 minute drive to the Fair Barn and Harness Track and a 10 minute drive to charming downtown Southern Pines.

Guest favourite
A well-maintained backyard features an inground pool surrounded by a manicured lawn. Red lounge chairs are positioned near the pool, while an inviting fire pit area with additional seating is set under the shade of nearby trees. Vibrant flowering bushes add color to the landscape.
Home in Southern Pines
4.94 out of 5 average rating, 174 reviews

Highland Hideaway/Pool & Fire Pit/$0 Cleaning Fee

Nestled in a peaceful neighborhood just a few miles from downtown Southern Pines and multiple world-renowned golf courses ⛳️ . A 3-bedroom / 2.5-bathroom home with a bonus room. Spacious open porches overlook an inground pool, perfect for those hot summer days, and a fire pit, perfect for relaxing during the evenings. This home is also a short drive to Fort Liberty and surrounding hospitals.

Popular amenities for Rockingham holiday rentals

Quick stats about holiday rentals in Rockingham

  • Total holiday rentals

    Explore 10 holiday rentals in Rockingham

  • Nightly prices starting at

    Rockingham holiday rentals start at £46 per night before taxes and fees

  • Verified guest reviews

    Over 410 verified reviews to help you choose

  • Wifi availability

    10 of Rockingham holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Gym, BBQ grill and Laptop-friendly workspace across Rockingham rentals

  • 4.7 Average rating

    Rockingham stays receive an average rating of 4.7 out of 5 from guests