Holiday rentals in Southern Pines

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Top-rated holiday rentals in Southern Pines

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Guest favourite

Farm stay in Vass

4.95 out of 5 average rating, 128 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.

7–14 Aug

$142 SGD per night

Guest favourite

Home in Southern Pines

4.99 out of 5 average rating, 139 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!

25 May – 1 Jun

$230 SGD per night

Guest favourite

Farm stay in Southern Pines

4.98 out of 5 average rating, 123 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.

2–9 Nov

$181 SGD per night

Guest favourite

Apartment 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

8–15 Dec

$122 SGD per night

Guest favourite

Guest suite in Southern Pines

4.86 out of 5 average rating, 140 reviews

The Suite Life - In-Law Apt, Private Entry, Fenced

Renovated, pet friendly in-law suite (downstairs unit) with a private entrance and no shared living space to the upstairs. Large fenced yard, and 1 mile to downtown So Pines, 6 miles to Pinehurst Resort, king size bedroom, full sleeper sofa, Keurig, a new kitchenette with oven, microwave, full size refrigerator, 50in Amazon Fire TV to link your accounts. A washer/dryer make it great for short term leases! The Suite also has a separate thermostat/A/C. Looking forward to hosting you!

7–14 Aug

$134 SGD per night

Guest favourite

Guest suite in Southern Pines

4.96 out of 5 average rating, 157 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!

30 Sep – 7 Oct

$137 SGD per night

Guest favourite

Guest house in Carthage

4.99 out of 5 average rating, 151 reviews

Charming 1 bedroom guesthouse on 4 acres, hot tub

Our guesthouse sits on 4 quiet fenced acres about 100 feet from our home. We are about 15 minutes from Pinehurst. Our large and friendly dogs greet you upon arrival and share the same fenced area as the guesthouse. Our barn conversion has a full kitchen, one queen bed and small fold out sofa. Coffee maker, wine fridge, fire pit with Adirondack chairs for evening glass of wine or to watch the fireflies. Saltwater pool from mid-May to Mid- Sep. Private two-person hot tub. Pet fee.

24 Feb – 3 Mar

$188 SGD per night

Guest favourite

Home in Southern Pines

4.99 out of 5 average rating, 144 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!

20–27 Sep

$173 SGD per night

Guest favourite

Cottage in Pinebluff

4.93 out of 5 average rating, 162 reviews

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.

30 Sep – 7 Oct

$160 SGD per night

Guest favourite

Home in Southern Pines

4.98 out of 5 average rating, 171 reviews

Charming, newly updated Downtown Cottage

Right in Downtown Southern Pines, Camellia Cottage is the perfect getaway! Walking distance to all of the wonderful restaurants, shops and breweries Downtown Southern Pines has to offer, and only minutes from some of the country's best golf courses! This updated 2 bedroom 1 bathroom home has all you will need in this home away from home. Enjoy the outdoors out on your newly landscaped patio, walk around and take in the beautiful sights of this charming Southern town.

4–11 Oct

$209 SGD per night

Guest favourite

Guest suite in Southern Pines

4.95 out of 5 average rating, 220 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.

5–12 May

$84 SGD per night

Guest favourite

Apartment in Pinehurst

4.99 out of 5 average rating, 102 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!

27 Sep – 4 Oct

$171 SGD per night