
Guesthouse vacation rentals in Southern Pines
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Top-rated guesthouses in Southern Pines
Guests agree: these guesthouses are highly rated for location, cleanliness, and more.

Quiet and Safe neighborhood Studio for 2
Enjoy a peaceful stay in this fully furnished studio for two, located in a quiet Southern Pines neighborhood. Atch. to the main house but fully soundproofed w/ a double wall, it offers a private key code entrance, queen bed, and a kitchenette w/ a hot plate and griddle. Step outside to your own private area with a fire pit. Just minutes from shopping, restaurants, breweries, golf courses, and movies. Only 15mins to the hospital, 20mins to Rockingham Racetrack, and 9mins to the Walthour Moss Fdtn

Storybook Tree House- 2 Mins to Local Breweries!
This space is perfect for the romantic couple getaway or a small group exploring Southern Pines! While rustic, we are located right near downtown, just a short distance (< 1mi) from restaurants, breweries, and cafes. We offer 𝙵̲𝚁̲𝙴̲𝙴̲ ✓Coffee and tea ✓Water and soda ✓Wifi ✓Mini fridge ✓Smart TV ✓Doggy bowls ✓Firewood ✓Fire pit ✓Extra blankets and towels ✓Self check in The property is shared with a single family home that is also available for rent here: https://airbnbcom/h/staypinehurst

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, friendly dogs greet you upon arrival and share the same fenced area as the guesthouse. Our barn conversion has a full kitchen, a queen bed and small sofa bed. 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 for dogs. sorry, no cats.

Peaceful retreat in the pines
Enjoy relaxing on the back deck in the trees after a long day of horse showing or several rounds of golf. 3 minutes to downtown Southern Pines eat dessert 1st at Ashtons or travel down the way to Pinehurst. This private charming apartment is lovely for enjoying all that the area has to offer. Soaking tub, kitchenette, office space and a big comfy bed. 18 minutes to the Carolina Horse Park, 3 minutes to downtown Southern Pines and 15 minutes to downtown Pinehurst, 6 minutesto downtown Aberdeen

The Kensington Cottage
Relax and unwind in our newly-renovated cottage, just a short walk from downtown Southern Pines! Spend the day admiring the beauty of the local trails and Sandhill Horticultural Gardens, or explore the quaint "SoPi" shops and Sunrise Theater. Only a ten minute drive to Pinehurst, the area boasts some of the nation's best golfing and a fabulous restaurant scene. The cottage features a new Nectar queen mattress, fast WiFi, an oversized shower, a modern kitchen, and a private yard with fire pit.

Charming Getaway Carriage House with pool
Welcome to our peaceful guesthouse in Southern Pines, NC! This contemporary retreat offers a serene escape with a pool, charming gazebo, and stunning views of the championship golf course, Pine Needles. The spacious unit is decorated in a modern style, providing a comfortable and inviting ambiance. Relax poolside or take a stroll through the well-manicured grounds. Golf enthusiasts will delight in the proximity to the renowned course. Discover tranquility and luxury in this hidden gem.

Bungalow at the Lake
Private guesthouse bungalow with lake access, on the property. 7 minutes from downtown Southern Pines. 15 minutes from Pinehurst Country Club. Apartment over garage with separate, private entrance and lots of parking space! Kitchenette with fridge and Keurig coffee maker, King size adjustable bed, large TV, private bathroom, and WiFi! Back yard amenities include fire pit, private dock, deck space, and lake access + kayak! Hosts on site and available for any issues during your stay.

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.

Carthage Country Guesthouse
This is a peaceful area with time to just slow down a little. Looking for a little peace & quiet? I have the place for you. Very cute Guesthouse nestled deep in the country area of Carthage. It's like taking a few steps back in time when life was simple. We are located within minutes to Pinehurst, Seven Lakes, Cameron, Pottery Highway and downtown Carthage. A very quiet area with nothing but the sounds of Mother Nature.

The Pinecone Carriage House
Nestled just minutes from Pinehurst and a mere block from downtown Southern Pines, the Pinecone Carriage House offers a perfect blend of convenience and comfort. The house itself, though unassuming, surprises with its cozy simplicity. Every detail has been thoughtfully curated to ensure a fantastic stay. Whether you’re here for golf, exploring the town, or simply unwinding, this house promises a memorable retreat.

The Cottage at Knollwood Manor
Relax at The Cottage, a private getaway situated on the Knollwood Manor estate next to the 15th Fairway of Mid Pines Golf Course. This quaint and cozy cottage is stocked with all of the necessities and conveniences to relax in The Pines and is situated at the ideal location for easy access to all local attractions.

Sunny Pines Hideaway
Escape to our stunning open-plan loft, nestled right outside of Pinehurst and everything it has to offer! You'll find yourself only minutes away from historic downtown Aberdeen, Southern Pines, and Pinehurst, allowing you to easily access a variety of shops, restaurants, and entertainment.
Popular amenities for Southern Pines guesthouses
Family-friendly guesthouses

Sunny Pines Hideaway

Quiet and Safe neighborhood Studio for 2

The Kensington Cottage

Horseshoe Pad Near Pinehurst Golf

Storybook Tree House- 2 Mins to Local Breweries!

Quaint Cottage Refuge in Historic Downtown

The Pinecone Carriage House

Solitude at The Shire 255 - Unit D - Downtown!
Guesthouses with a patio

Midland Cottage - King beds, Private entrance!

Steel Magnolia of Cameron Guest Cottage

Tannen Guest Suite w/ Hot Tub

The Carriage House on Connecticut.

Little Red Carriage House - Studio Apt.

Mighty Mesa (ADA compliant)

The Hen House on Broadway
Guesthouse rentals with a washer and dryer

Unique 2 Acres Creekside Retreat in Hope Mills, NC

Mystical Cottage

Adorable 1 bedroom guest house in Southern Pines

1 room for one person military discount
When is the best time to visit Southern Pines?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec | 
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $124 CAD | $126 CAD | $125 CAD | $125 CAD | $131 CAD | $122 CAD | $135 CAD | $132 CAD | $119 CAD | $124 CAD | $139 CAD | $125 CAD | 
| Avg. temp | 5 °C | 6 °C | 10 °C | 15 °C | 19 °C | 23 °C | 25 °C | 25 °C | 21 °C | 15 °C | 10 °C | 6 °C | 
Quick stats about guesthouse rentals in Southern Pines

Total vacation rentals
Explore 10 vacation rentals in Southern Pines

Nightly prices starting at
Southern Pines vacation rentals start at $84 CAD per night before taxes and fees

Verified guest reviews
Over 1,780 verified reviews to help you choose

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
10 of Southern Pines vacation rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Southern Pines rentals

5 Average rating
Southern Pines stays are highly rated by guests—averaging 5 out of 5!
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- Rentals with pools Southern Pines
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 - Rentals with a fireplace Southern Pines
 - Family-friendly rentals Southern Pines
 - Rentals with a patio Southern Pines
 - Rentals with a firepit Southern Pines
 - House rentals Southern Pines
 - Rentals with a washer and dryer Southern Pines
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