Holiday houses in Pittsboro

Juniper Cottage in the Grove

Art-filled with a boho feel, this home sits in a grove of cedars, feeling secluded and restful, but Main Street, filled with shops and restaurants and breweries, is just two short blocks away. Vintage touches and charm for days! Fully appointed Chef’s kitchen, and the sunlit den invite lounging and conversation, have coffee on the front porch, over looking the cedar grove, or enjoy the secluded back deck. Elegant luxury and quiet with town attractions just steps away! No third-party bookings.

Gem of a House by River near Chapel Hill

Escape to tranquility at this charming half-acre oasis next to a wondrous State Park and minutes from local hotspots. Sip tea on the porches overlooking lush gardens. Relax under the oak's dappled shade. Step inside to original wood floors, a modern kitchen, cozy beds, and artistic touches throughout. Whether solo or gathering with loved ones, this unique Bynum village retreat envelops you in calm. Stroll to the riverbank or through the funky town and let the rolling currents soothe your soul.

Loblolly House. Retreat.Pond&Pine. Cabin15minUNC.

Nestled amongst the loblolly pines, our renovated 1975 cabin is a 2 bedroom, 1 bathroom cozy, clean house in the woods, overlooking a 4 acre pond, with residential ducks. Escape from day-to-day life, with a feeling of being a million miles away, yet conveniently close to Chapel Hill & Pittsboro, 15 min S. of UNC & minutes from groceries & restaurants. Lux mattress & linens, dinghy, wifi, fire circle, fairy forest, spacious deck with pond view & a fire table, BBQ with lovely cafe lights awaits!

The Artist's Garret at Fearrington

Work remotely surrounded by art and nature. Enjoy art galleries, sculpture garden and nature trails. The Artist's Garret is a 1BR furnished apartment just 8 miles south of Chapel Hill. Artist Forrest Greenslade’s studio is just below. The Greenslade home is behind the studio and Garret. They are always around to see to guests needs and comfort. The apartment is meticulously cleaned and sanitized according to the AirBNB protocol. The air conditioning system is equipped with sanitizing UV light.

"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. For a reservation, there is a $30 per trip pet fee for each dog (Sorry, no cats). WiFi: See "Other details to note" below.

Curiously Cute B&B: Woodshed Unit

This refurbished container building built by an architect professor @ UNC Charlotte for a traveling art exhibit. This fabulous space has a queen bed, single futon, private bath & deck overlooking gardens w/ outsider folk art scattered about property. Mini fridge (holds 15x 12oz cans), coffee station w Starbucks Kcups & smart TV for streaming. Pass for FREE tasting @ Fair Game Distillery Included! Rates SINGLE OCCUPANCY add’l $20/person/night. Hammock, picnic tables, playground & firepit

Sunny, private, clean, accessible!

This cozy 2 bedroom adobe style solar home is light-filled, spacious, and is deep-cleaned with a fully equipped kitchen! One level entry/no steps. Walk in shower with grab bars. Private fenced yard for kids and dogs! Easy walk to town, library, trails, eateries and breweries. Tucked in an established neighborhood on the edge of the woods yet very private. Fast internet. Comfortable 2 BDR with queen / full sized beds. You will feel RELAXED! Welcome to the West End of Pittsboro!

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!

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).

Antique Farmhouse Near Pittsboro and Chapel Hill

Find peaceful privacy and casual charm at The Hotsy-Totsy, a Civil War-era farmhouse on seven secluded acres near the Haw River. You'll feel worlds away at this historical woodland farmstead, while being a quick country drive to the towns of Carrboro, Saxapahaw, and Pittsboro. This is an ideal setting for girls’ weekends, romantic getaways, small family gatherings, or just a sweet place to hang your hat if you're visiting the area.

Southern Front Porch, Newly Renovated, Comfortable

Set amid two acres this recently renovated house in the country is an easy 7 miles from UNC one direction and Pittsboro the other. This well appointed tranquil home features a great front porch and large lawn, a modern kitchen, games, and TVs in each bedroom. It has high speed internet and plenty of space to work or relax. With a couple or a crowd you may feel our most common feedback, "it feels comfortable and spacious."

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.