Cottage vacation rentals in Four Oaks

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!

Charming Vintage Cottage Circa 1906

My 1906 little house is completely restored farmhouse that my great grandparents brought to our property during the depression. Our guest cottage is tucked away behind the main house where we live. It has original shiplap boards in the open living room and kitchenette with beautiful pine floors throughout the 700 square-foot house. There is a separate bedroom with 12 foot lofted ceilings and plenty of natural sunlight throughout. We know you will feel good the moment you walk through the door.

Historic Downtown Cottage Across Community Garden

Cottage is centrally-located in historic downtown Smithfield. Close to I-95, Carolina Premium Outlets, 30 minute drive to Raleigh, North Carolina. During your stay relax in front of the fireplace, enjoy the front porch with a nice view of the community garden, or play with pets in the fenced back yard, which includes patio chairs around a fire pit and grill for a BBQ. Pet friendly cottage! Great for families, couples, friends, or business professionals looking for a comfortable place to stay!

😍 Downtown Cozy Cottage with Indoor Fireplace

Lovely cottage is conveniently located in downtown Smithfield with walking distance to shops and restaurants. Close to I-95, Carolina Premium Outlets, and 30 minute drive to Raleigh, North Carolina. Offers Keyless smart door check-in. During your stay relax in the rocking chairs of our front patio or enjoy the back yard with patio chairs around the fire pit and grill for a BBQ. Great for families, couples, friends, or business professionals looking for a cozy and comfortable place to stay!

Woodleaf Wayside

An 1850s cottage listed on the National Register of Historic Places was the Plantation Office for the Massenburg Plantation (Woodleaf). It was restored in 1990 and afterwards, became rental property. This two-story, cozy hideaway has a private drive and patio. Native stone and hand hewn beams in basement bedroom provide an unique stay. Full kitchen, modern bathroom, and washer/dryer. Come and go at your leisure. You will receive a keypad combination a day before your scheduled check-in.

Charming Cottage@Downtown Cary Park/ Private

Forget your worries in this spacious and serene location. Outside is the hustle and bustle of activity, but inside this private cottage, you'll have your own little haven! There is space to rest and relax, and you’re a short distance from anything and everything (only 10 minutes from RDU airport). We have a mix of vintage and modern furnishings to keep you comfortable, so come and enjoy your stay at Park Street Cottage! PS- I have a nice, twin air mattress for a 3rd guest, if interested.

Stepping Stone Cottage

Experience timeless moments at our unique family retreat, a historic cottage dating back to 1917. Combining historic charm with modern amenities, this tranquil haven is located near shops and restaurants. Enjoy a beautiful lake just steps away adding a natural touch to your stay. A quick 5-minute drive from I-95 and close to Fort Liberty Army Base, our cherished cottage offers convenience and comfort in one. Make lasting memories in this perfect blend of history, nature, and modernity.

Embassy of Oaks - Eclectic Peaceful Walkable Home

Small, eclectic, historic home tucked away in a peaceful neighborhood, in one of Raleigh's most convenient locations: right across the street from the Raleigh Little Theater and Rose Garden. Walking distance from the up-and-coming Village District, Hillsborough St., and NCSU. Cameron Village with its grocery stores, shops, and restaurants, is an easy 5-10 minute walk. A 10-minute drive from downtown Raleigh, the NC Art Museum, PNC Arena, and the Raleigh Flea Market/Dorton Arena.

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.

Old Blue's Retreat: Lakeview Cozy Cottage

Old Blue’s Retreat is minutes from Pinehurst & Southern Pines, NC. While the lake has been temporarily drained due to damage from tropical storm, Chantal, the property remains peaceful and inviting with wide-open views, abundant wildlife, and sunsets to remember. The cottage is furnished with charm to spare and offers 3 bedrooms, 2 baths, a full kitchen, spacious living area, and sunroom. Enjoy the sauna, fire pit, private dock, and easy access to golf, dining, and shopping.

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.

The Glam Cottage, Glamorous Southern Charm & cows.

Welcome to The Glam Cottage… a cozy, COW-tastic retreat in Wake Forest! Enjoy queen beds, a fully stocked kitchen, smart TVs, a pool table, board games, and lush, inviting décor. Outside, relax in the private fenced yard with a hot tub, fire pit, and boho gazebo. Minutes from Falls lake and walking trails with chances to spot local wildlife. Guests rave about how homey, peaceful, and well-equipped it feels, your perfect escape awaits! 🩷