Holiday rentals in Rockingham

Gorgeous Southern Home in Cheraw

Planning your next family reunion or friendly getaway? This beautiful and historic 5,354 sq. ft. 5-bedroom, 3.5-bath Cheraw vacation rental is the one for you. Featuring 5 living areas, a fully equipped kitchen, and a private fenced in yard, this lovely abode offers plenty of space for your group to spread out and feel at home. Be sure to pack your hiking boots or golf shoes and explore Cheraw State Park. Spend your evenings playing board games in front of any fireplace or enjoy the fire pit.

Farm Cottage | Peaceful Stay Near Laurinburg

Highland Games weekend available! Cozy farm house on the edge of town. This 2 king bedroom home with ensuite bathrooms, full kitchen and open living space offer peace & quiet of the country with the convenience of nearby local amenities. Dog friendly! Front porch rocking chairs and a large backyard invite you to relax. 2.5 miles to Downtown, 3.5 miles to central dining/shopping (Starbucks, Walmart, etc.), 18 miles/25 minutes to Rockingham Speedway, 30 mins to Pembroke, 35 mins to Pinehurst.

Chauffeur’s Apartment on Historic Property

Enjoy the former chauffeur's quarters located on the grounds of our National Register of Historic Places property that is a perfect stopover for traveling the I-95 corridor. 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.

Spacious 4 BD Home with Game Room!

Relax in our modern, spacious 4 bedroom, 2 ½ bathroom, new home in a quiet neighborhood! Just minutes from Pinehurst Golf Resort and downtown Pinehurst, Southern Pines, and Aberdeen. You can enjoy all the golf, breweries, restaurants, and shopping this charming tri-town area has to offer all within a 10-minute drive — Craft meals in our modern kitchen and cozy up after a day of exploring. And if you're working remote, super zippy Wi-Fi for all those video calls comes standard! Truly a gem!

Peaceful, rustic cabin on 20 acres, private pond.

Gather family or friends and escape to your own slice of nature at this cozy cabin tucked away on 20 quiet, wooded acres. Perfect for anyone seeking calm, privacy, and beautiful outdoor scenery. This property offers everything you need to unwind and recharge while close to restaurants and shopping. Enjoy fishing, sunsets over the pond, the sound of birds, and the kind of tranquility you can only find in the middle of nature. Reconnect and create new memories. Your peaceful getaway awaits.

Lovely Studio Apartment in Hamlet, NC

Relax in this peaceful studio 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 studio apartment is located in a 1950s home that has been split into three separate apartments. Each apartment has its own private kitchen, private entrance and exit.

The Steele House | Walk to Downtown

Welcome to your luxurious Airbnb nestled in the heart of the historical area of Rockingham, just a two-minute stroll from vibrant downtown. This exquisite retreat offers spacious rooms designed for comfort and elegance, perfect for unwinding after a day of exploring. Indulge in relaxation with a private spa tub, ideal for soothing your senses. Enjoy accessibility to a diverse array of shops and restaurants. The perfect blend of luxury, convenience, and history in this remarkable getaway.

The 19th Hole

🏌️‍♂️ Welcome to The 19th Hole, your ultimate home base in the heart of Pinehurst, North Carolina - where Southern charm meets championship golf! Perfectly tucked away, this spacious retreat combines style, comfort, and endless entertainment just minutes from the Village of Pinehurst and iconic fairways like Pinehurst No. 2, No. 4, and The Cradle. Whether you’re here to tee off, unwind, or celebrate with family and friends, The 19th Hole is where every day feels like a hole-in-one.

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.

Retreat on Pine - Close to Golf & Horse Park

Luxurious, 3 bedroom/2.5 bath home in walking distance to Downtown Aberdeen ~ Beautifully furnished with the latest home fashions and technology, it's ready to be your home-away-from-home. Just minutes from world renowned golf courses, Rockingham Dragway, exquisite dining and enveloped by southern charm, this covetable area will not disappoint! Spend your day exploring all this area has to offer or Retreat on Pine and catch up on your rest and relaxation.

Skipper Apt #4

This stylish place to stay is perfect for group trips. 1BR with full kitchen, bathtub, and comfortable sleeper sofa for additional guests or kids to sleep well. Close proximity to restaurants, Rockingham Motor Speedway, Highway 73/74 and US Route 1 and 220. Up to 4 units are available to invite family and friends to lodge in adjacent apartments. Units have everything you need to enjoy your home away from home stay.

Spacious Home: Laurel Hill, NC

Experience modern living in a cozy 3-bedroom house between Laurel Hill and Laurinburg. With essential amenities like a washer, dryer, and high-speed Wi-Fi, this house ensures comfort. Near I-74, it's 25 minutes from the University of North Carolina at Pembroke, 30 minutes from Hamlet, Rockingham, Aberdeen, Southern Pines, and Pinehurst, and 45 minutes from Fayetteville. Beaches and major cities are just 2 hours away.