Vacation rentals in Southern Pines

Cottage in Southern Pines

The entrance to a charming cottage is framed by lush greenery and well-maintained landscaping. A stone pathway leads to the front door, while a gravel driveway guides visitors through vibrant shrubs and trees.

4.96 out of 5 average rating, 373 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!

5 out of 5 average rating, 105 reviews

The exterior of a two-story cottage is shown, featuring a white clapboard façade with dark roofing. A covered porch is seen at the front, furnished with a small round table and four chairs, surrounded by landscaping with young plants and mulch.

Home in Southern Pines

New 5 Bedroom Cottage on Pine Needles Golf Course

New construction home on the golf course of Pine Needles Course between Pinehurst and downtown Southern Pines. Ideal location, close to everything the area has to offer. This 5 bedroom and 3 bathroom cottage is ideal for golf outings and family friendly vacations. Everything you need to make your stay ideal and comfortable. Main level: 1 bedroom, 1 bath, living room, kitchen, dining, office space, walk in pantry, laundry room. Second floor: 4 bedrooms, 2 bathrooms, abundant closet space.

Farm stay in Southern Pines

The exterior of the cozy barn cottage features a brick facade and white paneling, complemented by a shaded porch with seating. Two stable doors are visible, surrounded by lush greenery and tall trees, creating a serene country atmosphere.

4.99 out of 5 average rating, 188 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.

Guesthouse in Southern Pines

The Tudor Revival Carriage House is set amongst tall Longleaf Pines, with warm lighting emanating from its windows. The structure features a gravel driveway, dual garage doors, and is complemented by lush greenery around its perimeter.

4.98 out of 5 average rating, 255 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.

Home in Downtown Southern Pines

A cozy living room features a leather sofa complemented by colorful cushions. A wooden coffee table is set on a light area rug, with decorative items arranged on top. Dark green walls provide a backdrop for wall art and plants, enhancing the inviting atmosphere.

4.99 out of 5 average rating, 99 reviews

The Gallery - 2 bd Boutique Southern Pines Cottage

Enjoy a uniquely designed experience at this centrally-located place - whether in town for golfing, riding, or simply enjoying our quaint southern town. Just a block from Broad street's restaurants, shops, breweries and theatre, this two bedroom, two story cottage (and art studio!) has everything you need to enjoy Moore County. Relax in any of our carefully curated rooms, or take it outside to our backyard/vineyard for a summertime BBQ or a cozy fireside chat.

4.92 out of 5 average rating, 306 reviews

The kitchen features a large wooden island with a rustic design, surrounded by modern white cabinetry and stainless steel appliances. Abundant natural light filters through multiple windows, highlighting the wood beams above and the warm, welcoming atmosphere. A cozy seating area is visible in the background.

Cottage in Pinehurst

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

A guest suite features two double beds with light blankets, positioned beside wooden headboards. Two bedside lamps provide soft lighting, and a small nightstand sits between them. Natural light filters through two windows covered with blinds, illuminating the carpeted floor.

4.96 out of 5 average rating, 251 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.

Cottage in Southern Pines

A welcoming living area features a blue couch adorned with yellow pillows, complemented by a round ottoman. A small dining table is positioned nearby, and large windows allow natural light to fill the space. A light fixture hangs above, enhancing the room's comfortable ambiance.

4.97 out of 5 average rating, 195 reviews

Cottage on Ridge -Short & Extended Stays

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

4.98 out of 5 average rating, 290 reviews

A comfortable sitting area includes a gray sectional sofa paired with a round coffee table, adorned with small decorative items. Natural light enters through patio doors leading to a private garden. A queen bed with a light coverlet is positioned nearby, enhancing the cozy ambience.

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.

Home in Downtown Southern Pines

A small outdoor patio is presented with a round table and four black metal chairs. Lush greenery surrounds the area, providing a calm setting. The exterior of the cottage is gray, complemented by a dark front door and a welcoming pathway leading to the entrance.

4.96 out of 5 average rating, 212 reviews

Charming Cottage in Downtown Southern Pines

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 2 bedroom 1 bathroom home has all you will need in this home away from home. Enjoy the outdoors out on your own private patio, walk around and take in the beautiful sights of this charming Southern town.

Apartment in Southern Pines

A cozy living area is presented, featuring two tan accent chairs and a dark sofa. A wood coffee table is centered on a patterned rug. The kitchen area includes a bar with two brown stools, equipped with modern appliances and tasteful decor.

4.96 out of 5 average rating, 196 reviews

Tanglewood Farm B&B Horse Farm- The Fox Den Suite

Welcome to the Fox Den Suite at Tanglewood Farm! The Fox Den is a private one bedroom (KING) , one bathroom beautifully decorated apartment on our beautiful 10 acre horse farm. Nestled in the heart of North Carolina's beautiful horse county, just minutes from charming downtown Southern Pines. Enjoy local breweries, shops, amazing restaurants and over 100 beautiful golf courses. Weekend Breakfast for Two Sat and Sun Avail for Purchase at $30/morning

Bungalow in Downtown Southern Pines

The charming 1930's bungalow is framed by a white picket fence and flowering shrubs. A front porch is visible, inviting guests to enjoy the outdoors. Colorful blooms and greenery enhance the welcoming atmosphere, while a paved walkway leads to the entrance.

4.97 out of 5 average rating, 349 reviews

Delightful Bungalow in Historic Downtown

LITERALLY steps from the quaint downtown of Southern Pines. In the heart of the historic district of Southern Pines sits this charming, quaint & cozy 1930's bungalow. Just steps from our idyllic downtown of Southern Pines. (Literally 1 block!) You will be treated to a private, clean, cozy and updated space filled with everything you will need for a wonderful stay. 1 bedroom / 1 bath / 1 sleeper sofa. Street parking. Strict 'No Pet' policy.

Popular amenities for Southern Pines vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Southern Pines boutique hotels

The room features two spacious queen beds dressed in luxurious white linens, complemented by dark throw blankets. A wooden dresser is situated against the wall, with a television mounted above. Natural light enters through a nearby window, creating a bright and inviting space.

4.83 out of 5 average rating, 6 reviews

The Jefferson Inn Rm. 4 | Deluxe Guest Room

A spacious guest room is furnished with two queen beds, dressed in white linens and accented with dark throw blankets. Natural light floods the room, enhancing the wooden furniture. An oversized bathroom is visible in the background, featuring a door leading to elegant amenities.

5 out of 5 average rating, 9 reviews

The Jefferson Inn • Rm. 13 | Standard Guest Room

The Deluxe Guest Room features a spacious king bed with white bedding and a decorative gray throw. A tufted tan sofa is positioned next to a wooden coffee table, while natural light fills the room through bay windows adorned with plantation shutters.

4.5 out of 5 average rating, 4 reviews

The Jefferson Inn Rm. 7 | Deluxe Guest Room

A cozy sitting area features a tufted sofa in warm tones paired with a wooden dresser showcasing multiple drawers. Natural light enters through several shuttered windows, illuminating the room's rich hardwood flooring. A decorative plant sits atop the dresser, adding a touch of greenery.

The Jefferson Inn Rm. 15 | Junior Suite

A spacious guest room is designed with a wooden bed frame and crisp white linens. Soft gray pillows accentuate the bed. Nightstands with modern lamps provide gentle lighting, enhancing the serene atmosphere of the space.

The Jefferson Inn • Rm. 8 | (ADA) Standard Room

A spacious suite is shown, featuring two queen beds with white bedding and dark accent pillows. Covered French doors lead to another room, while light streams through the partially opened window, highlighting the warm wooden furnishings and neutral tones of the decor.

5 out of 5 average rating, 3 reviews

The Jefferson Inn • Rm. 9 | Standard Suite

A sitting area is visible, featuring a tufted brown sofa beside a wooden side table and lamp. Covered french doors lead to the bedroom, which contains a spacious bed with white linens. Natural light filters in through a window, highlighting the warm wooden flooring.

The Jefferson Inn • Rm. 2 | Standard Suite

4.95 out of 5 average rating, 21 reviews

A well-appointed sleeping area features two beds adorned with white quilts and decorative pillows. Framed floral artwork adds a touch of elegance to the wall. A small nightstand is placed between the beds, providing convenience and charm.

Hotel room in Robbins

Solomon's Inn - Downtown Robbins, NC. Room 3

Other great vacation rentals in Southern Pines

Guesthouse in Southern Pines

A studio layout is presented with a spacious bed featuring soft linens and decorative pillows. A small dining table with stools is positioned near a modern kitchen equipped with stainless steel appliances. Light wood flooring complements the neutral wall color, enhancing the open feel of the space.

5 out of 5 average rating, 42 reviews

The Kensington Cottage

Guesthouse in Southern Pines

The guest house features a bright exterior with a welcoming porch adorned with black and white chairs. A flag is displayed, and lush greenery surrounds the area. The pool reflects sunlight, complementing the serene atmosphere of the jungle-like backyard.

4.92 out of 5 average rating, 210 reviews

Mystical Cottage

4.95 out of 5 average rating, 137 reviews

A grassy pasture is enclosed by weathered wooden fencing, with tall trees and wooden structures visible in the background. The sky exhibits a mix of clouds and sunlight, creating a tranquil outdoor scene.

Farm stay in Vass

Peaceful Horse Farm Retreat

4.81 out of 5 average rating, 133 reviews

Condo in Pinehurst

Entire Condo · Greenview Retreat · Walk to PCC

Bungalow in Southern Pines

A charming bungalow is set amidst tall trees, showcasing a screened porch with multiple windows. The exterior features a neutral-toned facade surrounded by greenery and landscaped grounds. Sunlight filters through the trees, creating a serene outdoor setting.

4.94 out of 5 average rating, 111 reviews

Crosswind Farm

Apartment in Southern Pines

A well-appointed studio features a queen bed with a white blanket, a dark blue sofa, and a stylish rug in varied colors. A small table with two chairs and a potted plant enhance the space. Natural light fills the room through a large window adorned with dark curtains.

5 out of 5 average rating, 86 reviews

Private&Comfortable Studio for 2 in Southern Pines

Guesthouse in Downtown Southern Pines

The exterior of the cottage features a light-colored facade with a gabled entrance. A gravel driveway leads to a nearby garage, while two chairs and a small table are situated on the front porch, surrounded by landscaping with trees.

4.85 out of 5 average rating, 118 reviews

Solitude at The Shire 255 - Unit D - Downtown!