Holiday rentals with outdoor seating in Pittsboro

Shabby Chic Studio near UNC!

Charming 1-bedroom snuggled away 3 miles from UNC. Lots of character + natural light. Free bus stop across the street. It's on the highway, behind a privacy fence and trees so the traffic noise is muted. Great for UNC games, the hospital, and visiting students. Also perfect for larger groups when booked with our sister space on the property, "The Cozy Bungalow - Noted 'Historic Home' near UNC." Check out the space description to read about all the features and how the house is laid out!

White Oak Hill, minutes to UNC & Duke

Have everything you need for a hassle-free Chapel Hill/Carrboro retreat at this perfectly appointed home just 6 miles west of the city. Newly remodeled to please with luxury finishes inside and out, this vacation rental is highlighted by serene and beautiful country views from every window. This spacious layout sleeps 10 with 4 bedrooms, 2 full bathrooms, 1 half bath, 2 living rooms, bar seating and separate dining room. Foodies will love cooking in the fully equipped gourmet kitchen!

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.

Anna Belle's Retreat - Belle (Side B)

This renovated duplex offers tranquility, style and comfort. Situated in the North Chatham area, we are just a short drive to Chapel Hill and Pittsboro. Jordan Lake and Haw River are also close by. Nestled in the pines yet within walking distance to nearby shopping, you'll experience the peacefulness of being in the country with the conveniences of being in the city. Enjoy the private screened porch with adjoining patio and grilling area. Need more space? Unit A is also available.

Lovely farm cabin experience

Connect with nature in this unforgettable farm setting. Take in serene views from the deck or walk around to enjoy a variety of sweet animals including sheep, horses, goats, alpacas, emus, cows, ponies and more. The space is a fully furnished apartment in an adorable stone cabin with one queen bedroom, kitchen, full bath, laundry, high speed Wi-Fi, and outdoor hot tub. Upper cabin is also available as a separate rental (sleeps 5) listed as Log Cabin at the Farm on Airbnb.

Modern Tiny House Near Duke & Downtown

You’ll feel like you’re getting away from it all in this modern, private tiny house in the trees, even though you’re just minutes from Duke, downtown Durham, shopping, and restaurants. It’s the perfect balance of peaceful retreat and city convenience. The home includes all the essentials — full kitchen, laundry, A/C, and high-speed internet — but many guests find themselves spending most of their time relaxing on the screened-in porch, listening to birds, and recharging.

Downtown Pittsboro Boho Loft

Industrial loft in downtown Pittsboro - walk to everything or just relax on the spacious deck and enjoy music from the City Tap or Havoc! You will be in the heart of everything with easy access to the shops, bakeries, wine store, restaurants, breweries and other Pittsboro attractions. Loft is furnished comfortably with a king Murphy bed, pull out sofa bed, and wet shower with heated floors, heated towel rack and a stocked kitchen. Come enjoy industrial chic in comfort!

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

Secluded Treehouse - 27 acres on Terrells Creek

Private “Treehouse” Home on 27 acres in the woods. Enjoy Walking trails, creek, fire pit, outdoor games, hammocks, swings . 20 mins to downtown Pittsboro, Carrboro, Chapel Hill, Jordan Lake -40 mins to Raleigh, Cary and Durham but worlds away from it all. Come relax and remember what it’s like to be away from noise and light pollution and hear only crickets at night. 1 King bedroom + private loft with king and queen beds. (loft accessed by stair ladder).

Cozy Tiny house near UNC

Explore this cozy 400 square feet retreat around a 15 minute drive from UNC. The tiny house behind the main house in the gated yard. Enjoy the open floor plan with a full bathroom with a walk-in shower, kitchenette, and a charming patio. It is the perfect for sports fans and travelers seeking a Chapel Hill getaway with all the comforts of home! Hosts are close by to help with request during your stay. Pets are welcomed!

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). See house/pet rules before booking.

Guest House @ Mission Farm, quiet, farm setting

18 minutes to down town Chapel Hill/Franklin Street or historic & quaint downtown Pittsboro. Relax in a beautiful farm house on 10 acres near the Haw River with rolling pastures, woods, chickens, ducks, cows and and pond views. GREAT couple weekend getaway, those traveling to UNC/Duke sporting events, families with kids. Can interact with animals and relax in serene setting