Holiday rentals in Pinehurst

Cottage in Southern Pines

4.96 out of 5 average rating, 352 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!

4.99 out of 5 average rating, 112 reviews

Long Drive On No. 5 - 1BR Condo, GREAT Golf Views

Renovated, centrally located condo in Pinehurst - only a 10 minute walk to the Pinehurst Golf Clubhouse! "Long Drive On No. 5" is a newly renovated, second-story one-bedroom condo perfectly located on hole #16 of Pinehurst No. 5 Golf Course. Relax on the private back deck with open views of the fairway and enjoy the sunshine and unparalleled peace and quiet. Cozy & luxurious finishes combined with an excellent location make this condo perfect for a weekend golf getaway or an extended stay!

Guest favourite

4.95 out of 5 average rating, 239 reviews

Walkable Golf-Front Clean + Comfy Pinehurst Condo

Welcome to our clean, comfortable condo in the heart of Pinehurst golf! This top-rated ground-floor home stands out with its well-stocked kitchen, cozy furnishings and decor, great views (the screened back porch faces Pinehurst course #3), free parking and easy walkability. It's convenient to all of Pinehurst - the historic village's shops and dining, Fair Barn, harness track, resort, clubhouse, hospital/medical facilities, etc. - and just a few minutes to Southern Pines and Aberdeen.

4.96 out of 5 average rating, 219 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.

Guest house in Southern Pines

4.98 out of 5 average rating, 240 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.

4.98 out of 5 average rating, 780 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 favourite

Cottage in Pinehurst

4.92 out of 5 average rating, 294 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.

Guest suite in Southern Pines

4.96 out of 5 average rating, 244 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.

4.99 out of 5 average rating, 276 reviews

Flat in Pinehurst

Pinehurst #6 Garden Getaway

A warm welcome to our cozy 1 BR/1 BA apartment in the Pinehurst #6 community. It has a queen bed and a queen sofa bed if needed. We are close to the Village of Pinehurst and dozens of amazing Golf courses. We are less than 2 miles from First Health Moore Regional Hospital. Nearby you can enjoy shopping, dining, 4 local breweries and a winery. We also offer housekeeping for only $ 10 a day. PLEASE LET ME KNOW, when booking IF YOU NEED THE SECOND BED.

Guest house in Southern Pines

4.95 out of 5 average rating, 505 reviews

Quaint Cottage Refuge in Historic Downtown

LITERALLY steps from the quaint downtown of Southern Pines. In the heart of the historic district of Southern Pines sits this cozy eclectic 1930's cottage. Guests will have the entire cottage for their private use. This cottage is filled with unique & eclectic furnishings. Come, stay and enjoy! Spend time on the private screened in porch. Grab a book and relax in the hammock. Central HVAC 1 bed / 1 bath / 1 sofa bed Strict 'No Pet' policy.

4.99 out of 5 average rating, 107 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!

5 out of 5 average rating, 114 reviews

The Duffer's Drop - 2BR/2BA Condo in Pinehurst, NC

Enjoy your stay at a fully renovated 2BR/2BA condo right across from Pinehurst's historic Fair Barn and Harness Track. Situated on No. 5, a short approach shot from the Pinehurst Clubhouse, the Duffer's Drop has everything you need for your golf getaway. Relax on the porch overlooking No. 5, work on your culinary skills in the beautiful kitchen, or just catch some rest between rounds. The Duffer's Drop is the exactly what you're looking for!

Holiday rentals for every style

Get the amount of space that is right for you

Flats

Convenient locations with everyday essentials

Houses

A space that's all yours, with room for everyone

Hotels

Stylish accommodation and amenities

Popular amenities for Pinehurst holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Pinehurst

5 out of 5 average rating, 94 reviews

Greenside Getaway️! Walk to Clubhouse and Cradle!

JeffRating, 5 stars3 weeks ago

Great spot for a weekend golf trip. Easy to check in, nice back porch and comfortable beds. The showers are large and redone too. A+ all around.

5 out of 5 average rating, 26 reviews

Pinehurst National 9 Condo

MollyRating, 5 stars2 months ago

The condo is darling and we appreciated all the little extras--tissue boxes in every space, throw blankets, and coffee. There was an issue with the air conditioner the first night but Erin and Jackie responded immediately and had everything fixed by the time we returned from golfing. The condo overlooks the golf course and has a lovely balcony. The neighborhood is very quiet and peaceful. We would definitely stay here again the next time we are in Pinehurst!

5 out of 5 average rating, 45 reviews

Million $ Golf-front view + 3 Master BR + Peloton

ChrisRating, 5 stars2 months ago

We absolutely LOVED our stay! Home was stunning, beautifully decorated, very clean, and smelled wonderful. The community was stunning and my wife felt very safe walking our dog around the community each evening. We loved that each bedroom had its own en suite bathroom. That was a big bonus in our opinion. It was like each individual family had their own hotel room, but in a beautiful home. Erin was great at communicating and we will definitely stay here again if given the chance.

Guest favourite

4.96 out of 5 average rating, 24 reviews

Treehouse Retreat on Pinehurst Golf Course

AmyRating, 5 stars1 month ago

Cozy little treehouse just as pictured & convenient to Pinehurst, Southern Pines & Aberdeen. The cottage has everything you need. It was blissfully quiet at night & the feeling of being in the trees with views of the golf course, lake & pond are lovely. Victoria is a fantastic host. We’d love to return!

5 out of 5 average rating, 72 reviews

Cheerful Eclectic Pinehurst home

JenniferRating, 5 stars1 month ago

Donna's place in Pinehurst is a real charm. From the moment you are walking down the sidewalk up to the house, you feel right at home. it is extremely comfortable and welcoming inside with all amenities that one would need. We definitely recommend for anyone wanting a place in beautiful Pinehurst. It is so very convenient to shopping and wonderful restaurants...although grilling out back with family is wonderfully relaxing too. We will surely book again!

5 out of 5 average rating, 15 reviews

Banjos Golf Retreat!

BenitaRating, 5 stars1 week ago

This was perfect! This location was the perfect spot for my bridesmaids and I to get ready in the morning of my wedding. The house was SO spacious, private, easily accessible, and quintessentially beautiful. The backyard was so relaxing, and we just could not get enough of it! The host was spectacular, I loved staying here. Can’t wait to come back to Pinehurst and stay here again!

5 out of 5 average rating, 21 reviews

Townhouse in Pinehurst

Pinehurst Manor - Beautifully Renovated 2B/2B

AndrewRating, 5 stars2 months ago

Lance was super helpful and very accommodating. Place was super clean easy to find and he was flexible about our arrival time. Thank you hope to see you again soon.