Vacation rentals in Five Points

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Top-rated vacation rentals in Five Points

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Guest favorite

Farm stay in Vass

4.95 out of 5 average rating, 129 reviews

Peaceful Horse Farm Retreat

Anahata is a quiet farm retreat dedicated to peace and healing. You’ll stay in our Hunt Box - a spacious studio apartment over the barn with pasture view and fully equipped kitchen. There is space to roam and animals to greet. Please read the full listing prior to booking to ensure that this is the right place for you. For more pics, check out our Insta @anahatafarm. NO third-party bookings - please do not book this room unless you will be the one staying here. NO SMOKING. All are welcome here.

Oct 2 – 9

G$21,775 GYD per night

Guest favorite

Cottage in Southern Pines

4.96 out of 5 average rating, 278 reviews

The Ace Cottage - Tiny-home Feel, Close to golf

Unwind in the privacy of this adorable cottage! 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, bathroom with efficiency shower, a bistro set, and a Kitchenette (sink, dishes, Keurig, microwave, mini fridge with 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!

Dec 25 – Jan 1

G$23,608 GYD per night

Guest favorite

Apartment in Laurinburg

4.98 out of 5 average rating, 347 reviews

Chauffeur’s Apartment on Historic Property

Be our guest in our cozy and comfortable apartment that has everything needed for a relaxing stay. Enjoy the former chauffeur's quarters located on the grounds of our listed historic property with a view of the tranquil courtyard garden of the Manor House. The kitchen is complete and the comfortable full-sized bed should provide a good night's rest. Downtown is within walking distance. There are multiple seating areas to enjoy the gardens on the one acre grounds shared with the main property.

Jun 27 – Jul 4

G$20,833 GYD per night

Guest favorite

Home in Pinebluff

4.99 out of 5 average rating, 100 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), Downtown Southern Pines ( 7 miles), Rockingham Dragway (14 miles), Carolina Horse Park (10 miles), and Fort Bragg (16 miles) . We're also surrounded by over 20 beautiful golf courses and a wide variety of dining options within 11 miles of this completely renovated home that has been created specifically for your comfort and enjoyment.

Jan 14 – 21

G$37,509 GYD per night

Guest favorite

Home in Southern Pines

4.99 out of 5 average rating, 141 reviews

Restored 1920s 2BR Cottage w/Bikes-DWTN So Pines

Experience downtown Southern Pines in a stylish fully restored early-1900's cottage. This home is conveniently located 4 blocks (4 min walk) from Broad Street, where you will find all the shopping, restaurants, and bars. The cottage is 5 minute drive to several world-class golf courses (Mid-Pines, Mid-South, Longleaf, Pine Needles, Pinehurst No. 9, Talamore) just to name a few... and only 10 mins away from the Village of Pinehurst and Pinehurst No.2. Cruise like a local on the free bikes!

Mar 22 – 29

G$30,421 GYD per night

Guest favorite

Farm stay in Southern Pines

4.98 out of 5 average rating, 126 reviews

Finally Home Farm Bed and Barn

Bring your horse and your golf clubs! Welcome to Finally Home Farm Bed and Barn! A private 1 bedroom barn converted into a quaint cottage. Located on a peaceful farm just 2 miles from downtown Southern Pines, 1 mile from the back gate of Ft. Bragg and next to Weymouth Woods State Park, Finally Home Farm is the perfect place to explore all the Sandhills has to offer. *We are horse ($40) and dog friendly ($50) pet fee with Pre-Approval. Please include this info in your pre-booking.

Mar 28 – Apr 4

G$27,146 GYD per night

Guest favorite

Condo in Southern Pines

4.92 out of 5 average rating, 157 reviews

Relaxing in the Pines

Located 5 min from downtown Southern Pines (Broad St). A great place to stay for golfers, horse lovers, and others visiting to explore Pinehurst, Southern Pines and other surrounding areas. The large screened in porch off of the living room and dinning room which provides peaceful beauty and elegance. Two bedrooms and two full baths, this condo provides you with a wonderful opportunity for anyone wanting to relax and especially for golfers, horse lovers and others..5 PM Check in

Dec 6 – 13

G$18,606 GYD per night

Guest favorite

Guest suite in Southern Pines

4.96 out of 5 average rating, 158 reviews

Studio in the Pines ~ Minutes to downtown SoPines!

Surprisingly spacious, exceptionally clean, and completely private, this studio boasts everything a savvy traveler needs and more! Located minutes from downtown Southern Pines and from a plethora of world-class golf courses, restaurants, and shopping, this is the perfect space whether you're in town for a night or for a week. Easy commute to Ft. Bragg. Kevin & Chelsea (the hosts) live in the attached main house, but this studio is completely separated giving you plenty of privacy!

Oct 15 – 22

G$21,008 GYD per night

Guest favorite

Home in Southern Pines

4.99 out of 5 average rating, 146 reviews

Loft Cottage on Ridge ? Short & Extended Stays?

This 1930s cottage is the perfect spot for your stay in downtown Southern Pines. It is located on a quiet street, yet close enough to walk to all the shops/restaurants downtown or the Weymouth Center for the Humanities. This loft unit has a private entrance from the top of the stairs with 1 bedroom (Queen) & 1 bath, a full kitchen, and shared laundry room downstairs in the back of the home. Unit features vintage kitchen! Come stay with us for a short stay or extended stay!

Jan 30 – Feb 6

G$22,186 GYD per night

Guest favorite

Home in Fayetteville

4.92 out of 5 average rating, 760 reviews

TheHiddenCottage/4m to I-95/Wheelchair Accessible

Whether you are driving north/south or south/north we are the perfect stopover on your I-95 trip! We aim to provide you with a clean, safe, cozy, comfortable and welcoming place where you can either spend one night on a travel stopover or several nights if the Fayetteville/Ft. Liberty (formerly Ft. Bragg) area is your destination. Our space is private, easily accessible (all on one level; no steps on the property anywhere), kid, pet & EV friendly and conveniently located!

Dec 4 – 11

G$20,128 GYD per night

Guest favorite

Guesthouse in Southern Pines

4.97 out of 5 average rating, 212 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.

Aug 26 – Sep 2

G$21,723 GYD per night

Guest favorite

Home in Fayetteville

4.98 out of 5 average rating, 294 reviews

Modern and Rustic 3 bed/2 Bath Retreat

A modern rustic home with personal touches in a quiet neighborhood located in Fayetteville. It's great for a walk or run. Approximately 5 minutes to Ft Bragg, 10minutes from Raeford, 25 minutes from I95 and 25 minutes to the airport. The house has three bedrooms all with queen sized beds. The kitchen is fully equipped for individuals who like to cook. The living room is equipped with a television and a roku. A washer and dryer is available for use in the garage.

Jul 6 – 13

G$23,938 GYD per night