Cottage holiday rentals in Four Oaks

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!

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.

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 15 min to the famous Pinehurst Resort and Carolina Horse Park. Features a King size Nectar bed, Roku TV, WiFi, shower with tankless water heater, a bistro set, and a Kitchenette (sink, dishes, Keurig, microwave, mini fridge, 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!

Eclectic & Spacious Guest Cottage

Eccentric décor & art adorn the Guest Cottage walls and outsider art is scattered about the gardens. This handicap accessible unit has a king sized bed and a queen size Murphy bed, living room, kitchenette with coffeemaker, 2 burner cooktop, microwave, toaster oven & minifridge w/ freezer compartment. By the front door, is a small patio with vintage lawn furniture (seats 4) and a coffee table. Rates are TRIPLE OCCUPANCY An additional $20/ person/night applies. Pet friendly w/ pet fee.

Stepping Stone Cottage

Experience timeless moments at my 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 Bragg Army Base, my cherished cottage offers convenience and comfort in one. Make lasting memories in this perfect blend of history, nature, and modernity.

Close to Pinehurst Golf & Horse Park

The Happy Hangout has it all: Quiet setting with a fully fenced-in back yard, close to Pinehurst golf courses & the historic downtowns of Southern Pines, Pinehurst and Aberdeen. The Happy Hangout is close to Pinehurst (10 min), Southern Pines (10 min), Camp McKall (15 min), the Carolina Horse Park (20 min) and Fort Liberty (Bragg) (45 min). Our house is pet-friendly. The pet fee is $25 per stay and is included if you indicate during booking that you will be bringing a pet.

Cedar Serenity – Private Romantic Retreat

This peaceful haven gives couples and business travelers a retreat of comfort and calm for both leisure and remote work. Sink into a plush king bed, refresh in the oversized shower with three invigorating heads, and share coffee on the screened porch before an evening soak in the hot tub on your private patio. With high‑speed internet and a secluded 10.5‑acre setting, it’s an easy escape that feels a world away in Chatham County. And only 15 min from Pittsboro

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! 🩷

Friendship Cottage

Minutes from restaurants/shopping, this cozy cottage sits in front of a working goat farm while maintaining a private entrance/yard. Handicapped friendly, incl. paved drive, wide doorways, zero entry shower, no stairs. Modern amenities. 16x80 Dog Run. Rock on the porch, play in the yard, see the horses on a walk to the pond (not seen from cottage). Wooded trail accessible from pond is .7 mile. See house/pet rules before booking.

Restored Cabin on Heritage Farm.

Built in the 1930's from a Rehoboth Beach cabin design; the "Clubhouse" was built for out-of-town city guests to get a little peace and quiet in rural NC. Newly refurbished, family friendly, with plenty of forested land for exploring, camper/trailer parking and fenced pasture with water. Free wi-fi. Pets welcome - two pet limit. Pasture may be suitable to horses who won't jump the fence and can get along with 3-4 heifers.