Family-friendly vacation rentals in Chatham County

Quirky Fun B&B: Tree House Unit

Refurbished container building by an architect professor at UNC-C for a traveling art exhibit A space efficient room (8’x8’) w/ a tall, airy ceiling, full size bed, private bath, Mini fridge (holds 10x 12oz cans), coffee station w Keurig etc, smart TV for streaming & deck overlooking gardens w/ outsider folk art scattered about property. Pass for FREE tasting @ Fair Game Distillery Included! Rates SINGLE OCCUPANCY add’l $20/person/night applies. Hammock, picnic tables, playground & firepit

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.

"Enchanted Forest Garden" A One Bedroom Retreat

A 600 s.f. cottage retreat designed by Robert Phillips. One bedroom, full bath and kitchen, and spacious living room. Ten ft. ceilings and fine architectural details; terraced; fountains nestled in a tree grove on 10 acres with foot paths. 15-20 minutes to Chapel Hill/Carrboro, University of North Carolina; Pittsboro and the Saxapahaw arts community on the Haw River. When making a reservation there is a $30 per trip pet fee for each pet. WiFi: See "Other details to note" below.

Piece of Heaven Airbnb, Wedding, and Event Center

Our Home is Set on 100 acres of Pines , a Mile From Stress, and The Rocky River as a back drop, This Piece of Heaven is waiting for you. ( please note we allow for wedding and other events but those charges are not included with an Airbnb rental) Our 150+ yr old home is modernized uniquely to bring nature closer with 1700 sq ft of deck space, and a River View deck that is so peaceful. If you are thinking Event/ Wedding, we would love the opportunity to earn your business.

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.

Country place close to all Triangle locations

Beautiful setting on 8 acres near Jordan Lake and the American Tobacco Trail - 30 minutes or less to RDU, RTP, Raleigh, Durham and Chapel Hill. Full use of a private 2 bdr guesthouse with a spiral staircase leading to a loft bedroom. Downstairs, soaring 20 foot ceilings and huge windows look out on our horse pastures. Ideal for fishing stays - less than 10 minutes from Jordan Lake, and plenty of parking. Level 2 EV charging available.

Calming Woodland Octagon

Take a much needed break from the stresses of the city at this unique property nestled in old growth woodland. Indulge in the sound of the wind and a sea of stars. Make friends with your neighbors: deer, squirrels, hawks and fireflies. A haven for writers, artists, dancers, remote workers and nature lovers only 15 minutes from Chapel Hill and 8 minutes from Jordan lake. You'll find Zen, fiber internet, and more than a little magic here.

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.

Downtown Pittsboro Glamtastic

Pittsboro's only selfie wall! Enjoy this unique bungalow furnished in Hollywood Regency glam style with easily walkable access to all downtown amenities. Relax on the spacious front porch or enjoy the back yard fire pit. Walk to downtown merchants and spend the day antique shopping or enjoy food and beverages from a variety of local eateries. New kids park with splash pad is just around the corner at Chatham Park!

Second Home in Pittsboro, NC

This newly remodeled home is on 4 wooded acres in Pittsboro. It is one mile from Chatham Park, and close to the downtown shops and restaurants. It is convenient to drive to Jordan Lake, Fearrington Village, Chaple Hill, Apex, and Cary. Chatham County is one of the fastest growing in the state, but Pittsboro retains it's historic and eclectic roots. We are pet-friendly, with a fenced in backyard.