Holiday rentals with outdoor seating in Pittsboro

Grandma’s House - Minutes from UNC with Firepit

Looking for something fancy? Then keep moving! Grandma’s House is comfy, clean, and without a lick of fance. Enjoy a quiet getaway at a peaceful cottage-- just 10-15 min from UNC-Chapel Hill and UNC Hospital! The location combined with the full kitchen, fast wifi, parking, memory foam mattresses, and hosts just a holler away make Grandma's House the best way to enjoy your visit to town. As a bonus, Grandma loves to leave snacks for her guests. Bring your furry friends, too! Gramma don't mind.

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!

Amelia Farms; Relaxing Retreat on 30+ Acres

This 2-bedroom, 1-bathroom cottage is nestled amidst a canopy of oak trees, offering peace and tranquility. **Please note:** The pasture is currently empty. We are pet-friendly (with a fee; some restrictions apply. Please see below for details). The property features a ¾-mile wooded trail winding past century-old barns and through a mature hardwood forest. Enjoy easy access to Greensboro, Burlington, Liberty, Asheboro, High Point, and the new Toyota plant.

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 Secluded Accessible West Wing

The West Wing is guest quarters to a residence on 15 acres 5 miles south of Chapel Hill. It's an easy 10 minutes (5 miles) to downtown Chapel Hill, UNC, UNC Hospitals and Carrboro. Comfortable, clean, attractive, and very secluded. It is a studio apartment with one double bed, perfect for one person, cozy for two.. Your friendly, well behaved dog is welcome, but don't ever let your dog on the furniture or leave your dog alone uncrated. Sorry, no cats.

Retreat to Historic Home in a Private Arboretum

Unwind and renew your spirit in our updated 5 bedroom (sleeps 9) historic house (circa 1830's) in the heart of the largest arboretum of its kind in the USA. Explore our exotic 206 acre property sheltering 4000 different North American and international tree species. Hike through old growth forest past historic outbuildings and watch the sun sparkle on our ponds. We are family and pet friendly, 25 minutes to Duke University, 17 minutes to UNC Chapel Hill.

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.