Vacation rentals in Rockingham

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Top-rated vacation rentals in Rockingham

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Guest favorite
A charming home is featured with a welcoming front porch, flanked by rockers and adorned with American flags. Lush green lawns surround the house, and well-maintained hedges provide a clear view of the inviting entrance. Tall trees create a serene atmosphere in the yard.
Home in Cheraw
5 out of 5 average rating, 7 reviews

Miss Nancy's Place

Come enjoy your stay in this charming Centry plus old home located in the beautiful Historic District of Cheraw. Come see why this town was labeled "the prettiest place in Dixie" by General Sherman during his occupation of Cheraw in 1865. The front porch with rockers and a porch swing are a guest favorite. Quiet neighborhood where neighbors greet you with a wave as they walk their dogs. Centrally located within walking distance to downtown and locally owned restaurants, antique stores, gym, ect

Top guest favorite
A small cabin features a covered back patio with a circular table surrounded by four chairs. The exterior showcases a light-colored siding with green trim and large windows that allow for natural light, all set against a backdrop of tall pine trees.
Home in Ellerbe
5 out of 5 average rating, 58 reviews

the Loblolly getaway

Unplug at the Loblolly. Enjoy peace and quiet in our one bedroom home set on 37 acres of pines bordering many acres of state land. We do not have cable TV, however we have a DVD player with a dresser full of DVD movies! Take a walk. Bring your mountain bikes and hit the state land trails. Sit on the 3 season porch and watch the birds, or read. Eat out on the back patio. We are 20 minutes from Pinehurst, 25 from Rockingham. 5 minutes from interstate 73. Full kitchen plus washer and dryer.

Top guest favorite
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 favorite
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 favorite
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.
Apartment 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 favorite
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.
Apartment 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 favorite
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 favorite
Home in Pinehurst
4.98 out of 5 average rating, 816 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
The welcoming front porch showcases a bright white exterior with black trim. Hanging plants and vibrant floral decorations add color. The landscaped yard features blooming azaleas and gravel pathways, creating an inviting entrance. A series of steps lead up to the covered porch area.
Home in Hamlet
5 out of 5 average rating, 18 reviews

3 Bedroom Cozy, Warm, Inviting & Charming

Rest peaceful in this tranquil getaway. Words like charming, cozy and unique are an understatement when describing this beautiful home. A super clean home built in the 1950's. This home still has many of those same attributes but with many updates. Spacious / large bedrooms with TV's in each bedroom. Brand new posturepedic mattress and purple mattress. Original hardwood floors, a new remodeled kitchen with brand new stainless steel appliances.

Guest favorite
A modern kitchen features white cabinetry and a wooden countertop, with stainless steel appliances including a refrigerator and an oven. A sink with a sleek faucet is positioned next to a wall-mounted microwave. Natural light filters through the nearby window, highlighting the clean, functional layout.
Apartment in Hamlet
5 out of 5 average rating, 26 reviews

Cozy, Comfy Apartment Near Downtown

Settle in with two bedrooms, two bath rooms and even a queen sleeper sofa, if you need it. Completely renovated and stocked kitchen with all new appliances and cookware. Corner dinette set with seating for six. Plush mattresses, soft 100% cotton linens! More improvements and pictures to come, including a desk and chair for remote work! We’d love to host you in our wonderful space while you’re here for work, vacation or just visiting.

Top guest favorite
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.
Guesthouse 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 favorite
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 places to stay

Quick stats about vacation rentals in Rockingham

  • Total vacation rentals

    Explore 10 vacation rentals in Rockingham

  • Nightly prices starting at

    Rockingham vacation rentals start at ﺩ.ﺇ220 per night before taxes and fees

  • Verified guest reviews

    Over 410 verified reviews to help you choose

  • Wi-Fi availability

    10 of Rockingham vacation rentals include wi-fi 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