Vacation rentals in Southern Pines

A dining area is viewed, featuring a wooden table surrounded by black chairs. A light fixture hangs above the table, while a sliding glass door allows natural light to fill the space. The kitchen area is visible, showcasing white cabinetry and modern fixtures.

4.82 out of 5 average rating, 299 reviews

The Perfect Lie in Pinehurst!

This is the perfect getaway spot for enjoying all that Pinehurst has to offer. Situated on fairway 2 of #5, this is a sweet golfer's retreat, walkable to Pinehurst Country Club and the Cradle! Walk across the street for breakfast at the Harness Track or take a short stroll to the Village. This 2bedroom unit is completely private with 2 double beds in each room plus a sleeper sofa. Laundry facilities are just outside the unit in a building across the parking lot. Dogs welcome. No cats please.

4.97 out of 5 average rating, 159 reviews

The interior features a wooden staircase leading to an upper loft area, framed by natural wood paneling. A comfortable seating arrangement with a small coffee table is positioned in front of a brick fireplace, complemented by a patterned area rug.

Cottage in West End

Juniper Pines Cottage

A very nice place to stay! Nestled in a peaceful, yet convenient area near Pinehurst "home of golf", North Carolina, our cottage invites the traveler to a pleasantly rustic setting. Built in 1943, our lovely cabin is completely renovated and filled with country charm. ATTENTION!!! PLEASE READ THIS & HOUSE RULES BEFORE SENDING INQUIRY. *PROFILE VERIFICATION MUST INCLUDE GOVERNMENT ID (ie, state issued license) *FOR THE HEALTH & SAFETY OF ALL GUESTS, WE MAINTAIN A NO PETS, NO EXCEPTIONS POLICY.

A warmly colored dining area is highlighted by a large round table surrounded by eight black leather chairs. Natural light enters through tall arched windows, complementing the rich orange walls and decorative white wainscoting. A classic chandelier hangs above, adding elegance.

4.98 out of 5 average rating, 126 reviews

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.

4.95 out of 5 average rating, 235 reviews

Guest-Favorite Golf Condo! Clean, Cozy, Comfy

Welcome to The Sonder Condo, our clean and comfortable ground-floor condo in the heart of Pinehurst! This top-rated vacation rental stands out with its well-stocked kitchen, cozy furnishings and decor, great views (back porch faces Pinehurst #3), plentiful free parking and easy walkability. It's convenient to all of Pinehurst - the historic village, Fair Barn, harness track, resort, clubhouse, hospital/medical facilities, etc. - and just 10-15 minutes to downtown Southern Pines and Aberdeen.

The modern kitchen features a spacious island with two wooden bar stools. Above, three pendant lights provide illumination. A sleek backsplash complements the stainless steel appliances. The open layout allows visibility into the adjoining living areas, enhancing the bright and airy atmosphere.

5 out of 5 average rating, 103 reviews

Newly renovated farmhouse style open concept.

Completely renovated, stylish 3-bedroom condo is perfect for group trips & Junior golf families. Newly renoved with wide open floor plan in main living area. Gourmet kitchen, 3 incredibly comfortable bedrooms and 2 brand new stunning bathrooms. Includes private laundry room in condo, coffee bar, big screen TV’s in every room, built in bench area in kitchen, very spacious living and dining area off open concept kitchen, and screened in porch out back. Condo is walking distance to The Cradle.

A ping pong paddle rests beside a white ball on a sleek black tabletop. The table is situated in a well-lit space, with faint reflections visible on its surface, suggesting an area designed for recreational activities.

4.9 out of 5 average rating, 115 reviews

The Chatham House

The Chatham House is a privately-owned 3 bedroom/2 bath vacation home located in the famed Pinehurst #6 - just minutes away from the Village of Pinehurst shops and restaurants. This home-away-from-home features everything you need for a relaxing/fun vacation. Whether you have come to play some of the best golf courses in the world or have come for a fun family vacation, the Chatham House is your place to stay! Also great for Doctors and Nurses as First Health hospital is just minutes away.

4.98 out of 5 average rating, 105 reviews

An open kitchen area showcases modern appliances, including a stainless steel refrigerator and microwave. A granite countertop forms a breakfast bar with four black stools. The space is well-lit with pendant lighting, complemented by white cabinetry and a view of natural light through the window.

Villa in Pinehurst

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.

A decorative glass pumpkin sits atop a white pedestal. The pumpkin is a vibrant blue color with intricate patterns reflecting light, set against a backdrop of greenery visible through a nearby window.

4.95 out of 5 average rating, 112 reviews

"Perched in Pinehurst"

Should you decide to visit the picturesque town of Pinehurst, then look no further? Perched in Pinehurst, is less than a half mile from The Pinehurst Resort, and is nestled between Golf Course #5 and The Harness Track. If you are attending a function at The Fair Barn, driving will be optional, because you can easily walk across the street. In addition, you will find plenty of wonderful shopping and dining opportunities nearby. Check out my social media page "Perched in Pinehurst"

4.94 out of 5 average rating, 107 reviews

A gravel patio area is furnished with several adirondack chairs arranged around a fire pit, overlooking a tranquil lake. Tall trees surround the space, with autumn leaves scattered on the ground. The setting offers a peaceful retreat with scenic views.

Cottage in Lakeview

Old Blue's Retreat: Lakeview Cozy Cottage

Old Blue’s Retreat is located minutes away from Pinehurst and Southern Pines, NC. Enjoy lake views from every room in the house. The house is comfortably furnished with charm to spare. Enjoy the private dock for fishing, swimming, or sunning. Relax in the wood burning sauna after a day of golf or swimming. Gather around the fire pit for s’mores. Excellent golf, restaurants, & small business shopping all around. Old Blue is outfitted with everything you need to stay comfortably.

The exterior view features a modern home with large windows offering a glimpse of the interior. A patio with a table and chairs is set on concrete, surrounded by a neatly maintained yard and a white picket fence, creating a welcoming outdoor space.

4.97 out of 5 average rating, 34 reviews

⛳ Golf & Family Bungalow - Convenient to Village

Beautiful and very clean home located only 1 mile from Pinehurst Country Club and the Village of Pinehurst. Great indoor and outdoor living spaces make this bungalow retreat perfect for your visit to Pinehurst. Great for golfers, groups, and families. Happy to host remote workers or those looking to move to the area. Fully equipped kitchen (coffee, utensils, cookware), bedrooms (linens, comforters), and baths (soap, shampoo, conditioner) to make your visit a pleasure. 🌟🌟🌟🌟🌟

A golf course fairway is visible, featuring lush green grass and a gentle slope. Tall pine trees provide shade on one side, while sand traps can be seen in the distance. The blue sky is filled with wispy clouds, enhancing the serene landscape.

4.96 out of 5 average rating, 211 reviews

Pinehurst Green - 2BD 2BA Golf Front Condo

Welcome to Pinehurst Green, located in the heart of Pinehurst golf! Our 2BD, 2BA condo is within walking distance of the Pinehurst clubhouse and the 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 min drive to the Fair Barn and Harness Track and a 10 min drive to charming downtown Southern Pines.

4.92 out of 5 average rating, 197 reviews

A wooden deck offers a view of the surrounding greenery and the calm waters of the lake. Trees and bushes frame the scene, with a rock outcrop visible across the water. Natural light illuminates the outdoor area, enhancing the serene setting.

Cottage in Pinebluff

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.

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Popular amenities for Southern Pines vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Stay near Southern Pines's top sights

Betsy's Crepes69 locals recommend

Ironwood Cafe54 locals recommend

Weymouth Woods - Sandhills Nature Preserve43 locals recommend

Southern Pines Growler Company41 locals recommend

Chapman's Food and Spirits39 locals recommend

Ashten's37 locals recommend

Boutique hotels in Southern Pines

A lounge area is shown with elegant chandeliers illuminating the space. Dark wood accents frame the room, featuring seating arrangements with comfortable chairs and a tufted sofa. A large painting adorns the wall, adding a classic touch, while ambient light filters through large windows.

4.4 out of 5 average rating, 5 reviews

The Jefferson Inn • Rm. 5 | Deluxe Guest Room

A tree-lined street presents a charming view of brick buildings and boutique storefronts. Lush greenery from nearby planters complements the sidewalk, while parked cars line one side, providing a sense of community and activity in this inviting urban setting.

4.8 out of 5 average rating, 5 reviews

The Jefferson Inn Rm. 4 | Deluxe Guest Room

The lounge area features plush seating arrangements with tufted leather sofas and elegant armchairs. Crystal chandeliers illuminate the space, where rich wooden details and dark walls provide a sophisticated atmosphere. A framed artwork depicting a serene equestrian scene adds a touch of character to the room.

5 out of 5 average rating, 3 reviews

The Jefferson Inn Rm. 7 | Deluxe Guest Room

The lounge area features elegant chandeliers hanging from dark wood ceilings. Richly toned walls are complemented by comfortable seating arrangements, including tufted armchairs and a plush couch. Light from large windows illuminates the space, creating a sophisticated atmosphere perfect for relaxation.

5 out of 5 average rating, 9 reviews

The Jefferson Inn • Rm. 13 | Standard Guest Room

The lounge area features a rich color palette with dark wood accents and plush seating. Elegant chandeliers provide ambient lighting, while a framed painting hangs on the wall. Leather couches and armchairs are arranged around a coffee table, inviting relaxation and conversation.

5 out of 5 average rating, 3 reviews

The Jefferson Inn • Rm. 9 | Standard Suite

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Other great vacation rentals in Southern Pines

4.94 out of 5 average rating, 53 reviews

An outdoor deck is furnished with four lightweight chairs surrounding a round table. The natural wood surface contrasts with the greenery of the surrounding trees and the clear blue sky, creating a serene spot for relaxation.

Home in Southern Pines

New Pines Retreat -Brand new home!

A bright hallway showcases a carpeted staircase leading to the upper level. Natural light filters through the open door at the end, highlighting a small seating area with greenery. The walls feature simple decor and a round clock is mounted near the entrance.

4.91 out of 5 average rating, 23 reviews

Cozy 2 bedroom condo near Pinehurst golf courses

4.95 out of 5 average rating, 38 reviews

A cozy fire pit area is surrounded by five gray chairs arranged in a circular pattern. The fire pit is constructed from stone, with a warm flame flickering at the center. Soft lights illuminate the surrounding gravel and grassy area, creating an inviting ambiance.

Home in Southern Pines

The Oakmont Cottage

A modern home is set amidst tall trees, featuring a white facade with dark trim. A welcoming front porch is visible, adorned with potted plants. The well-maintained lawn is complemented by a gravel path leading to the entrance, highlighting the peaceful surroundings.

4.97 out of 5 average rating, 77 reviews

Farmhouse at No. 6

A private outdoor space is depicted, featuring a hot tub with a protective cover. Two white lounge chairs and a small table are positioned nearby, surrounded by natural foliage. The area is paved with brick and offers a serene atmosphere, complemented by the greenery in the background.

4.94 out of 5 average rating, 50 reviews

Pinehurst - Fantastic Location!

5 out of 5 average rating, 87 reviews

A spacious living room features a cozy seating arrangement with light brown leather sofas and two dark armchairs. A flat-screen television is mounted above a decorative fireplace. Natural light streams in through sliding glass doors, leading to an outdoor deck with additional seating options.

Home in Southern Pines

New 5 Bedroom Cottage on Pine Needles Golf Course

An outdoor patio area features a sleek black bar with high stools, overlooking lush greenery. A putting green is included, enhancing the space for leisure activities. Natural light floods in through expansive glass sliding doors, connecting the patio to the interior living area.

4.9 out of 5 average rating, 63 reviews

Pinehurst Golf, Weddings, Seminars with Hallmark A