Holiday houses in Pinehurst

Cottage in Southern Pines

4.96 out of 5 average rating, 355 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!

4.95 out of 5 average rating, 239 reviews

Guest Favorite Condo w/ Golf Views! Clean + Comfy

Welcome to your cozy Pinehurst retreat! Whether you're here for a golf tournament, a quick getaway or a longer stay, this clean, comfy ground-floor condo is a great home base. Enjoy a well-stocked kitchen, inviting furnishings + a screened porch with fairway views - perfect for morning coffee or evening wine! It's very close to the historic Village with shops + dining, plus the fair barn, harness track + Pinehurst resort/clubhouse. With its peaceful, well-located setting, it's a guest favorite!

4.92 out of 5 average rating, 137 reviews

THE NEST, 2BDR 2BA, 2nd Floor, WiFi, Cable, Pool

Our condo is centrally located and hugs the majestic shores of Lake Pinehurst! It’s tucked away at the top of the statuesque Lakeview Condominiums! So peaceful and quiet and yet only minutes away from Pinehurst Resort and CC, the charming Village of Pinehurst, and a plethora of great pubs and restaurants! Located on the second floor, this 2BR/2BA unit offers our guests gorgeous sunsets, quiet strolls, and the simple pleasure of green living! Come and be our guest! 🐾🌳

Guesthouse in Southern Pines

4.98 out of 5 average rating, 241 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.

Guest suite in Southern Pines

4.96 out of 5 average rating, 245 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, 277 reviews

Apartment 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.

Guesthouse in Downtown 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, 148 reviews

To The Green On #17 - Studio w/ GREAT Golf Views!

PERFECT LOCATION - only a 5 minute walk to the Pinehurst Golf Clubhouse! "To The Green On #17" is a second-story studio condo perfectly located on hole #17 of Pinehurst No. 3 Golf Course. Relax on the private back deck with open views of the fairway and enjoy the sunshine and unparalleled peace and quiet. Cozy yet luxurious finishes combined with an excellent location make this studio condo perfect for a weekend golf getaway or an extended stay!

4.99 out of 5 average rating, 108 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!

4.98 out of 5 average rating, 110 reviews

Cozy Pinehurst Retreat w/ Putting Green

Enjoy your Pinehurst stay in the family-friendly neighborhood of Village acres. The area is surrounded by The Greenway pedestrian and bicycling trail. The house is situated within 2 miles of downtown Pinehurst, Camelot Park, and Rassie Wicker Park, and is a short drive away from any of the many wonderful golf courses that Pinehurst has to offer. The house was recently remodeled and is well furnished, to make for a comfortable stay.

4.94 out of 5 average rating, 256 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.

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Popular amenities for Pinehurst holiday rentals

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Other great holiday rentals in Pinehurst

4.99 out of 5 average rating, 94 reviews

Perfect golf getaway - quick drive to all courses

AnneRating, 5 stars5 days ago

Beautiful home with an equally beautiful setting. The kitchen was well equipped. We spent an amazing time with family. There was plenty of room for all. Very comfortable. Hosts were great as they checked with us often to make sure all was well.

Superhost

4.88 out of 5 average rating, 32 reviews

The Green Tee Suite

JoRating, 5 stars1 month ago

This was a cute little condo and perfect for my stay. I was there alone so had plenty of room. It is ideal for 1 or 2 people. The location is terrific to navigate Pinehurst from and super close to the cute historic district. Would book again.

4.98 out of 5 average rating, 45 reviews

Fore on No. 5

SabrinaRating, 5 stars1 month ago

We loved staying here! It was close to the golf course and had everything we needed. Morning coffee on the back deck was incredibly enjoyable and so peaceful!

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.

4.95 out of 5 average rating, 20 reviews

Elegant Golf Front Condo w/ King, Walk to Village

FaithRating, 5 stars2 months ago

Place is beautiful and so worth the price! Everything is truly within walking distance, and being right on the fairway was such a plus. Beautiful spot, perfect for what we needed, and the area is so peaceful. Truly felt like a relaxing vacation! Highly recommend!

4.99 out of 5 average rating, 82 reviews

5 BR New Build! 5min to Golf & Village + Game Room

ConnorRating, 5 stars6 days ago

Wonderful stay. House included everything expected and had everything we needed to BBQ a nice meal for our group. Would definitely come back again!

4.93 out of 5 average rating, 61 reviews

Updated 2 Bed 2 Bath Golf Course Front Condo no. 5

Matt Rating, 5 stars6 days ago

Great place for us to stay during our daughter's wedding. Really liked the deck and view of the course. Thanks!