Vacation Rentals By Owner In Southern Pines, NC

Welcome to The Jefferson Inn, a timeless boutique hotel blending historic Southern charm with modern comfort. Located in downtown Southern Pines, it’s the perfect home base for weekend escapes, romantic getaways, golf trips, or work retreats. Enjoy coffee on the porch, relax in the 1901 Bar Lounge or patio, and experience warm hospitality in a refined, inviting setting.brbrWelcome to The Jefferson Inn, a historic boutique getaway in downtown Southern Pines!brbrRoom 4 is a beautifully appointed deluxe guestroom offering inviting comfort and thoughtful details - perfect for guests who want a refined stay without the need for a full suite. Located on the 2nd floor, Room 4 is accessible by one flight of stairs or elevator and features an open, airy layout with touches that feel both cozy and elevated.brbrWhy Guests Love This Roombr• Two comfortable queen beds - ideal for friends or family traveling togetherbr• Oversized bathroom with a walk-in rain head showerbr• Cozy sitting area tucked into a bright window alcove, perfect for morning coffeebr• Warm finishes and boutique styling throughoutbrbrRoom 4 offers the relaxed elegance The Jefferson Inn is known for, placing you just steps from downtown Southern Pines, while providing a calm, welcoming retreat at the end of the day.brbrMake sure to visit our 1901 Lounge, or outdoor patio space, for a craft cocktail during your stay! brbrThe Jefferson Inn is a digital entry property, allowing for easy check-in and check-out.brThere will be a $100 security deposit hold on your card at check in that gets released 7 days after check in provided there are no damages in the unit.

Southern Pines • The Jefferson Inn • Deluxe 2-Queen Guestroom

Southern Pines, North Carolina, United States

Bed

Bath

Sleeps

$199.39

Welcome to The Jefferson Inn, a timeless boutique hotel blending historic Southern charm with modern comfort!brbrLocated in downtown Southern Pines, it’s the perfect home base for weekend escapes, romantic getaways, golf trips, or work retreats. Enjoy coffee on the porch, relax in the 1901 Bar Lounge or patio, and experience warm hospitality in a refined, inviting setting.brbrRoom 12 is a spacious deluxe guestroom designed for comfort and relaxation - offering an inviting retreat after a full day exploring Southern Pines. Located on the 3rd floor, this well appointed room features a comfortable layout and thoughtful design elements that reflect The Jefferson Inn’s timeless boutique style.brbrWhy Guests Love This Roombr• Two comfortable queen beds with luxurious linensbr• Oversized walk in shower featuring both standard and rain shower headsbr• Warm, welcoming layout that feels relaxed and refinedbr• Deluxe finishes that elevate the guestroom experiencebrbrRoom 12 delivers the relaxed elegance and layered comfort The Jefferson Inn is known for, offering a peaceful retreat above downtown Southern Pines - just steps from dining, shopping, and nightlife.brbrMake sure to visit our 1901 Lounge, or outdoor patio space, for a craft cocktail during your stay!brbrThe Jefferson Inn is a digital entry property, allowing for easy check-in and check-out.brThere will be a $100 security deposit hold on your card at check in that gets released 7 days after check in provided there are no damages in the unit.

Southern Pines • The Jefferson Inn • Deluxe 2-Queen Guestroom

Southern Pines, North Carolina, United States

Bed

Bath

Sleeps

$199.39

Welcome to The Jefferson Inn, a historic boutique getaway in downtown Southern Pines!brbrRoom 7 is a spacious deluxe guestroom that blends classic charm with elevated comfort - perfect for guests who want a relaxing retreat with distinctive character. Located on the 2nd floor, this light filled room features beautiful bay windows and a welcoming layout designed for unwinding after a day exploring Southern Pines.brbrWhy Guests Love This Roombr• Comfortable king bed in a refined, spacious settingbr• Beautiful bay windows that flood the room with natural lightbr• Luxurious Chesterfield leather couch, ideal for relaxing or readingbr• Claw foot tub with shower combination, offering a timeless, spa like experiencebr• Boutique finishes that feel warm, elegant, and invitingbrbrRoom 7 delivers the timeless elegance and comfort The Jefferson Inn is known for, offering a peaceful place to recharge just steps from downtown Southern Pines.brbrMake sure to visit our 1901 Lounge, or outdoor patio space, for a craft cocktail during your stay!brbrThe Jefferson Inn is a digital entry property, allowing for easy check-in and check-out.brThere will be a $100 security deposit hold on your card at check in that gets released 7 days after check in provided there are no damages in the unit.

Southern Pines • The Jefferson Inn • Deluxe King Guestroom

Southern Pines, North Carolina, United States

Bed

Bath

Sleeps

Exceptional(1)

$199.39

Welcome to The Jefferson Inn, a historic boutique getaway in downtown Southern Pines! brbrRoom 8 is a thoughtfully designed standard guestroom offering comfortable accommodation and accessibility features — ensuring a welcoming and relaxing boutique stay for every guest.brbrThis ACC (accessible) room blends cottage style furnishings with elevated comfort, creating a calm, inviting atmosphere that feels both functional and refined.brbrWhy Guests Love This Roombr• Comfortable king bed with luxurious linensbr• ACC accessible layout designed for ease and mobilitybr• Accessible bathroom and roll in shower for added convenience and comfortbr• Classic cottage style furnishings with thoughtful details throughoutbrbrRoom 8 delivers the timeless elegance and comfort The Jefferson Inn is known for, offering a peaceful place to recharge just steps from downtown Southern Pines.brbrMake sure to visit our 1901 Lounge, or outdoor patio space, for a craft cocktail during your stay!brbrThe Jefferson Inn is a digital entry property, allowing for easy check-in and check-out.

The Jefferson Inn, Downtown Southern Pines, King Bed

Southern Pines, North Carolina, United States

Bed

Bath

Sleeps

$217.13

Welcome to The Jefferson Inn, a timeless boutique hotel blending historic Southern charm with modern comfort. Located in downtown Southern Pines, it’s the perfect home base for weekend escapes, romantic getaways, golf trips, or work retreats. Enjoy coffee on the porch, relax in the 1901 Bar Lounge or patio, and experience warm hospitality in a refined, inviting setting.brbrWelcome to The Jefferson Inn, a historic boutique getaway in downtown Southern Pines!brbrRoom 9 is a spacious, thoughtfully appointed suite that offers the perfect balance of comfort, privacy, and classic boutique style - ideal for longer stays or guests who appreciate defined living space.brbrLocated on the 3rd floor, this suite is accessible by two flights of stairs or elevator and features a well designed layout with separation between the bedroom and living area.brbrWhy Guests Love This Suitebr• Two comfortable queen beds in a private bedroombr• Elegant covered French doors separating the bedroom from the sitting areabr• Inviting living room with a leather Chesterfield couch, TV, mini fridge, and coffee setupbr• Well appointed bathroom with dual pedestal sinksbr• Oversized walk in shower with both standard and rain shower headsbrbrRoom 9 delivers the relaxed elegance and layered comfort The Jefferson Inn is known for, offering a peaceful retreat above downtown Southern Pines — just steps from dining, shopping, and nightlife.brbrMake sure to visit our 1901 Lounge, or outdoor patio space, for a craft cocktail during your stay!brbrThe Jefferson Inn is a digital entry property, allowing for easy check-in and check-out.brThere will be a $100 security deposit hold on your card at check in that gets released 7 days after check in provided there are no damages in the unit.

Southern Pines • The Jefferson Inn • Deluxe 2-Queen Suite

Southern Pines, North Carolina, United States

Bed

Bath

Sleeps

Exceptional(1)

$201.66

Welcome to The Jefferson Inn, a timeless boutique hotel blending historic Southern charm with modern comfort. Located in downtown Southern Pines, it’s the perfect home base for weekend escapes, romantic getaways, golf trips, or work retreats. Enjoy coffee on the porch, relax in the 1901 Bar Lounge or patio, and experience warm hospitality in a refined, inviting setting.brbrbrRoom 13 is a charming and well appointed standard guestroom offering comfort, simplicity, and boutique style - ideal for guests seeking a relaxed and welcoming stay. Located on the 3rd floor, this inviting room provides a peaceful setting to unwind after a day exploring Southern Pines.brbrWhy Guests Love This Roombr• Two comfortable queen beds with luxurious linensbr• Cottage style furnishings that feel warm and timelessbr• Smart TV for relaxing evenings br• Oversized bathroom with a walk in rain head showerbr• Thoughtful amenities designed for effortless comfortbrbrRoom 13 delivers the relaxed elegance and layered comfort The Jefferson Inn is known for, offering a peaceful retreat above downtown Southern Pines - just steps from dining, shopping, and nightlife.brbrMake sure to visit our 1901 Lounge, or outdoor patio space, for a craft cocktail during your stay!brbrThe Jefferson Inn is a digital entry property, allowing for easy check-in and check-out.brThere will be a $100 security deposit hold on your card at check in that gets released 7 days after check in provided there are no damages in the unit.

Southern Pines • The Jefferson Inn • Standard 2-Queen Room

Southern Pines, North Carolina, United States

Bed

Bath

Sleeps

$437.88

Discover this 3-bedroom house in Southern Pines. Inside, guests find a fantastic mix of comfort with a king bed, queen bed, sofa bed, and even a crib for little ones. Three bathrooms offer convenience, 2 full and 1 Half. Whether relaxing indoors or planning your next adventure on the golf course (12 minutes from the PCC Club, 7 minutes to Longleaf, 5 to any Ross Resort Course), at the stables/horse shows (20 minutes to Carolina Horse Park or 12 minutes to the Fairbarn), or pickleball tournaments, this delightful home provides a welcoming space to unwind while still having the convenience of walkability to Breweries, Restaurants, Wine shops, bars, shopping and our local Entertainment venue (the Sunrise Theater). Our place is equipped for both long or short stays to make your holiday/work trip an experience to remember.

Charming Walkable Downtown Southern Pines 3 bed/2-1/2 Bath!

Southern Pines, North Carolina, United States

Bed

Bath

Sleeps

$209.05

Downtown SoPi Vibes brbrStay in the heart of downtown SoPi — the perfect spot for travelers who want comfort and a little social spark. Walk to wine bars, pubs, coffee shops, boutiques, live music, and all the local favorites SoPi is known for.brbrWhether you're here for a weekend escape, a couple’s getaway, or a fun golf weekend, this condo makes it easy to eat, sip, explore, and enjoy everything SoPi has to offer — right outside your door.brbrYour downtown adventure starts the moment you arrive!

Condo

Wanderlust Bungalow on May - Downtown Adventure

Southern Pines, North Carolina, United States

Bed

Bath

Sleeps

Exceptional(39)

$848.21

One-of-a-kind historical estate overlooking the 15th fairway of the Donald Ross designed Mid Pines Golf Course in Southern Pines. Often described as having one of the ''best'' golf course views in The Sandhills, The Knollwood Manor was built in 1926 and lovingly cared for through the years. The elegance of this English Country Manor exists in concert with 2.06 acres of natural beauty. The sweeping back lawn overlooking the golf course is the perfect setting for entertaining or simply kicking back to enjoy life in The Sandhills. Residence features 5 spacious bedrooms on the second floor, all with private bath. Bedrooms facing the golf course have sleeping porches with additonal twin beds. Gourmet Kitchen, 2 fireplaces, hand-molded plaster ceilings & walls and the dramatic Formal Dining Room for large gatherings. Numerous historical architectural elements include original oak hardwood flooring, original slate roof, fluted glass doorknobs, vintage diamond patterned lead glass windows, and copper gutters. Outdoor lighting and ring doorbell camera at main entrance facing driveway for added security. Additional x3 cameras on north side of property and x1 on south side of property covering the side driveway and backyard/golf course area.brbrClose to the top golf courses in the Pinehurst / Southern Pines area, Fort Bragg, and other key attractions and dining.

Villa

Knollwood Manor - The Historic Mid Pines Mansion

Southern Pines, North Carolina, United States

Bed

Bath

Sleeps

Exceptional(30)

$266.39

Surrounded by world-class golf courses and boasting easy access to several museums, shops, and dining spots, this 3-bedroom, 2.5-bath vacation rental is the perfect place to kick off your upcoming trip to North Carolina! Centrally located just 1 mile away from the historic downtown stretch of Southern Pines and close to several horse farms, this home offers endless nearby activities. After a long day of fun, head back to this cozy retreat for a home-cooked meal and a relaxing night in.brbr-- THE PROPERTY --brbrProximity to Golf Courses | Free WiFi | ~14 Mi to Carolina Horse ParkbrbrBedroom 1: Queen Bed | Bedroom 2: Queen Bed | Bedroom 3: 2 Twin BedsbrbrOUTDOOR LIVING: Back deck w/ pergola, seating area, covered front porchbrKITCHEN: Fridge, natural gas stove/oven, dishwasher, microwave, cooking basics, toaster, coffee maker, paper towels/trash bagsbrINDOOR LIVING: Smart TV, gas fireplace, dining table, open floor planbrGENERAL: Linens, towels, washer & dryer, central air conditioning, ceiling fansbrFAQ: Stairs required to access, bedroom & bathroom on main floorbrPARKING: Free Street Parkingbrbr-- THE LOCATION --brbrATTRACTIONS: Downtown Southern Pines (1 mile), Sandhills Horticultural Garden (5 miles), Malcolm Blue Farm (5 miles), Aberdeen Fear Factory (6 miles), Union Station Railroad Museum (6 miles), Camelot Playground (7 miles), Carolina Horse Park Foundation (14 miles)brGREAT OUTDOORS: Downtown Park (1 mile), Reservoir Park (4 miles), Weymouth Woods (4 miles), Nick’s Creek Greenway (7 miles), Uwharrie National Forest (34 miles)brGOLF: Southern Pines Golf Club (2 miles), Talamore Golf Course (4 miles), Whispering Woods Golf Club (7 miles), Legacy Golf Links (8 miles)brAIRPORT: Fayetteville Regional Airport (40 miles)brbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smoking br- No pets allowedbr- No events, parties, or large gatherings br- Additional fees and taxes may applybr- Photo ID may be required upon check-inbr- NOTE: This property requires stairs to access

Cozy Southern Pines Retreat 1 Mi to Downtown!

Southern Pines, North Carolina, United States

Bed

Bath

Sleeps

Exceptional(2)

$363.3

Your Southern Pines getaway awaits at this delightful and spacious 4-bedroom house. With a mix of 1 king, 3 queen, 1 full, and 1 twin bed, this tranquil retreat is perfect for families or groups of friends. Enjoy the convenience of amenities like a washing machine, heating, AC, and WiFi. Three bathrooms with showers ensure everyone stays refreshed. Book now and enjoy everything this house has to offer.

Quirky Cottage - Downtown Southern Pines

Southern Pines, North Carolina, United States

Bed

Bath

Sleeps

Select Dates for Price

Downtown Southern Pines with easy access to Broad Street's shops, restaurants and breweries. This updated 2/2 has a spacious first floor with gas logs fireplace, kitchen with white cabinets, granite countertops and washer/dryer hookup. Upstairs you'll find both light-filled bedrooms. Rear door leads to a backyard with privacy fence and alley access to garage.brclosely located near to Fort Liberty, Fort Bragg, Camp Mackall.br

Charming 2-bedroom townhome in Downtown Southern Pines.

Southern Pines, North Carolina, United States

Bed

Bath

Sleeps

Exceptional(37)

$126.51

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!brThe wi-fi login information will be sent via the Airbnb app and is also posted in the unit. brbrWe do not have cable in the unit. The TV is a smart TV and has access to apps via Wi-Fi such as Hulu, Netflix, Amazon Prime, and others.

Loft Cottage on Ridge
Short & Extended Stays

Southern Pines, North Carolina, United States

Bed

Bath

Sleeps

Exceptional(43)

$168.22

Keep it simple at this peaceful and unique home. Located in the upstairs of The Estate and across from a Donald Ross Golf Course, Southern Pines Golf Club. This 2 Bedroom and 2 Bath Unit can sleep 6 adults comfortably.brThe kitchen is fully stocked, the unit is spacious, and the owners are just down the road if you need anything at all!brWe hope you enjoy your stay at this historic 1928 home, downtown Southern Pines and look forward to hosting you for short or long term stays!brbrPlease keep in mind this is an upstairs unit so steps will need to be climbed to access it.brbrThis unit has 2 bedrooms with 2 queen size beds. It also has a 3rd room with a trundle bed with 2 separate mattresses (one pulls out - see photos). Each bedroom has it's own private bathroom.brbrThe main living area has a smart TV. There is no cable in the unit, so it has all apps available with WiFi - Netflix/Hulu/Amazon Prime.brbrThe kitchen is fully stocked with spices, a KDUO (k cups/carafe), baking sheets, pots and pans, dishes, cooking utensils, olive oil, cookware. We will also have starter coffee available. The dining table has an additional 2 chairs to accommodate 6 people. brThe washer/dryer is inside the unit and we have a starter supply of laundry detergent.brbrThe 2 bathrooms include towels, washcloths, a blow-dryer, and starter shampoo/body wash.brbrWe are conveniently located close to the following locations:brSouthern Pines Golf Club - 0.2 milesbrPinehurst Resort - 5.6 milesbrCarolina Horse Park - 12 milesbrWeymouth Center for the Arts/Campbell House - 0.8 milesbrPine Needles Golf Course - 3.7 milesbrFort Bragg Proper - 27 miles to the gatebrbr*Please notify us in advance if you would like us to supply a pack n play, which will be provided at no extra charge*brbrWhen you pull up to the home, stay to the left-hand side of the house and park behind the house. There you will see a storm door on ground level. Once inside, take the wooden stairs up to the unit. This is a private entrance.brbrWe live 3 miles away and will be available if any issues arise.brShoot me a message on the AirBnB app and I will get back to you ASAP.brbrThis is a quiet, private, and mature neighborhood directly across from the Southern Pines Golf Club. This golf club is open to the public to play golf or grab a bite to eat and is easily accessible by foot. It is also approximately 0.5 miles from the city center of downtown Southern Pines - Broad Street.brThe wi-fi login information will be sent via the Airbnb app and is also posted in the unit. brbrWe do not have cable in the unit. Both TVs are smart TVs and have access to apps via Wi-Fi such as Netflix, Hulu, Amazon Prime.

Upstairs at the Estate - Across from SP Golf Club

Southern Pines, North Carolina, United States

Bed

Bath

Sleeps

Exceptional(3)

$304.69

Just a few miles from Downtown Southern Pines and a short drive to dozens of Golf Courses. This home is nestled in a cute neighborhood and has a nice pool and fire pit area to relax and enjoy with your family.

SoPi Home With a Relaxing Pool and Fire Pit

Southern Pines, North Carolina, United States

Bed

Bath

Sleeps

Exceptional(11)

$193.58

Sister unit in same building available if you need more space. Ask for details! Just 2.4 miles to Mid Pines, 2.4 miles to Pine Needles, 6.6 Miles to Pinehurst Resort and less than 10 minutes to Southern Pines. Up the steps you will enter this second-floor, single-level, condominium with 1,400 square feet. There is tons of light with many windows and two patio doors accessing the balcony. The modern decore has soothing paint colors with a touch of navy and gray. Enjoy a relaxing evening on the covered balcony overlooking the Hyland Hills fairway or in the den while watching the 55-inch smart tv in the comfortable sectional sofa. Kitchen/dining area is open to the den, so everyone can be together as you cook at the granite island. If you need to do a little work, a desk is provided and the home has high speed internet and WiFi. The bedrooms are on opposite sides of the home providing plenty of privacy. 43” Smart TVs in both bedrooms Each bath can be accessed from within the bedrooms with one bath also being accessed from the living area. The washer and dryer are located in the spacious laundry room off the hallway.

Condo

Renovated Golf Front! Short commute to Ft.Bragg - Pets Allowed Upon Approval

Southern Pines, North Carolina, United States

Bed

Bath

Sleeps

Exceptional(40)

$464.39

Welcome to A Cinderella Story, our cozy historic 4 bedroom cottage equipped with everything you need for your home away from home.brbrLocated minutes away from world-class golf, nationally renowned equestrian activities, and the relaxing Spa at Pinehurst. brbrA very short walk away to beautiful downtown Southern Pines - picturesque boutiques, delicious restaurants, coffee shops, a brewery, a movie theater and more!brbrComfortably sleeps 14 for golf trips, family retreats, and girlfriend getaways. brbrThe house features:brbrBedroom 1 - 1 king bed with full linens, Smart TV brBedroom 2 - 1 queen bed with full linens, ensuite bathroom and a Smart TVbrBedroom 3 - 2 pyramid beds with trundle and full linens (sleeps 6)brBedroom 4 (located upstairs) - 2 twins beds with full linens. A full bathroom is across the hall with a clawfoot tub for a nice bubble bath. brbrThere are 3 full bathrooms downstairs stocked with toilet paper, shampoo, conditioner, body soap and hair dryers. brbrMake yourself at home with our open space fully equipped kitchen - microwave, coffee maker, toaster, fridge, gas stove and oven, dishwasher, pots and pans, plates, cups, silverware…etc to cook your favorite meals. Grab a barstool at the welcoming kitchen island and enjoy your favorite snacks and drink. brbrAdjacent to the kitchen is a beautiful long dining room table that seats 10 people- a perfect place to come together for a meal or play one of the numerous board games you can find on the bookshelf. brbrA cozy living room with a Smart TV, several accent chairs, and a sleeper sofa (to accommodate extra guests) is the perfect gathering place to unwind after a fun day of exploring the town or playing a round of golf. brbrNeed to get some work done Around the corner from the living room is a small private workstation. brbrExpansive fenced in backyard with gas grill, outdoor games and secluded fire pit with chairs to enjoy a relaxing evening. New in 2022 is a professionally installed putting green. brThere are 5 hole locations and it rolls like the real thing. There is also an outdoor 10x10x10' hitting bay to help you get warmed up before your next round. brbrThe house and linens are professionally cleaned by a third party cleaning service. brbrRelax, unwind and escape to the charm of the North Carolina Sandhills.

A Cinderella Story -Downtown Southern Pines

Southern Pines, North Carolina, United States

Bed

Bath

Sleeps

$216.0

Welcome to The Jefferson Inn, a timeless boutique hotel blending historic Southern charm with modern comfort! brbrLocated in downtown Southern Pines, it’s the perfect home base for weekend escapes, romantic getaways, golf trips, or work retreats. Enjoy coffee on the porch, relax in the 1901 Bar Lounge or patio, and experience warm hospitality in a refined, inviting setting.brbrPerfectly suited for shorter stays, solo travelers, or couples who plan to spend more time exploring than staying in, our Petite Queen Room offers a smart, all-in-one layout that blends comfort with simplicity.brbrThis cozy space features a plush queen bed, a sleek ensuite bathroom with shower, and just what you need for a restful, easy stay—without the excess. Every detail is thoughtfully curated to maximize comfort while keeping things uncluttered and inviting.brbrLocated within the charm and character of our boutique hotel, you’ll enjoy the same elevated design, quality linens, and welcoming atmosphere as our larger rooms—just in a more intimate setting.brbrIf you’re looking for a stylish, no-fuss retreat in a prime location, the Petite Queen Room is a perfect fit.brbrWhy Guests Love This Roombr• Comfortable queen bed with soft, luxurious linensbr• Private ensuite bathroom with modern finishesbr• Smart, space-saving design that feels cozy—not crampedbr• Cottage-inspired touches that add warmth and characterbr• Perfect for shorter stays, solo trips, or minimalist getawaysbrbrMake sure to visit our 1901 Lounge or outdoor patio space for a craft cocktail during your stay!brbrThe Jefferson Inn is a digital entry property, allowing for easy check-in and check-out.

Downtown Southern Pines - The Jefferson Inn - Petite Queen Room

Southern Pines, North Carolina, United States

Bed

Bath

Sleeps

Exceptional(13)

$150.59