Holiday houses in Pittsboro

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Pittsboro

Guests agree: these stays are highly rated for location, cleanliness and more.

%{current} / %{total}1 / 1
Top Guest favourite
The exterior view of a charming two-story home is presented, featuring a green wooden facade and a well-maintained landscape. A pathway leads to the entrance, with a porch area visible and surrounded by lush greenery, creating a serene outdoor space.
Apartment in Fearrington Village
4.98 out of 5 average rating, 287 reviews

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.

Top Guest favourite
A cozy living area features a soft gray sofa adorned with bright throw pillows, accompanied by a tactile red blanket. A light wooden shelf displays framed art and plants above. A mustard yellow chair and traditional rug add warmth, while natural light filters through sheer curtains.
Home in Pittsboro
4.95 out of 5 average rating, 177 reviews

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.

Guest favourite
A serene garden space is presented, featuring a small pond surrounded by natural stone and ornamental plants. A decorative bell hangs prominently in the foreground. In the background, a vintage bus serves as a unique building amidst lush greenery.
Tiny home in Chapel Hill
4.94 out of 5 average rating, 183 reviews

Cozy Art Cabin among organic gardens near UNC/Duke

This is a shabby-chic art-studio cabin. It has a stunning walk-in shower w/ an under-water mural mosaic. There are mosaic doors & windows throughout the space. This space shares a common wall with my mosaic art studio. There are 2- sweet Aussie shepherds and 2- domestic cats on the property. Guests are welcome to eat meals on the back deck or beautiful gardens. There is a private shower, sink & composting toilet in cabin. New kitchenette recently added. Would like a long-term day-shift renter.

Superhost
A bright guest suite features a comfortable king bed adorned with a colorful quilt. Natural wood walls and ceiling create a warm ambiance, while large windows provide views of the surrounding trees. A private entrance is visible beside the staircase leading into the suite.
Guest suite in Chapel Hill
4.87 out of 5 average rating, 448 reviews

Art, Beauty, Nature: A Woodland Retreat

Relax in our bright and artistic guest suite — all hand-built with unique touches throughout. -Private entrance & terrace -Comfortable king-sized bed -Smart TV -Kitchenette with small refrigerator, microwave, toaster oven -Private patio w/ patio lights & seating for 2 -Unique art -Complimentary coffee & tea Great for getaways, rest, retreats, time in nature! 15 mins from restaurants, cafes and the charming towns of Carrboro, Pittsboro, and Saxapahaw. 10-15 mins to Chapel Hill, 20 to UNC.

Guest favourite
The exterior of the container building is shown, featuring a metallic façade and a striped awning over the entrance. A numbered sign is mounted beside the door, while two wooden chairs are placed nearby, surrounded by greenery.
Shipping container in Pittsboro
4.91 out of 5 average rating, 192 reviews

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

Top Guest favourite
A cottage retreat is nestled among tall trees, surrounded by lush greenery. Soft lighting glows from large windows, reflecting off a small pond with gentle water movement. Stone pathways and a rustic bench invite exploration of the serene outdoor space.
Tiny home in Pittsboro
4.97 out of 5 average rating, 192 reviews

"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.

Guest favourite
A cozy living area showcases a light-colored sofa adorned with patterned pillows, positioned beside a wooden table. Exposed brick walls and a rustic wooden ceiling enhance the industrial aesthetic. The kitchen area is visible in the background, featuring dark cabinetry and modern appliances.
Apartment in Pittsboro
4.93 out of 5 average rating, 121 reviews

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!

Top Guest favourite
A serene creek meanders through a lush forest, with smooth stones lining its banks. Sunlight filters through the canopy of green leaves, creating dappled shadows on the water's surface. The tranquil scene invites exploration and connection with nature.
Farm stay in Pittsboro
4.96 out of 5 average rating, 111 reviews

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).

Top Guest favourite
A wooden cabin is nestled among lush green trees, surrounded by a natural landscape. A winding path leads to the entrance, lined with simple outdoor lighting. The tranquil setting is embraced by the vibrant foliage, creating a peaceful retreat atmosphere.
Home in Chapel Hill
4.92 out of 5 average rating, 140 reviews

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.

Top Guest favourite
A cozy tiny house is nestled in a lush, green yard, surrounded by trees and foliage. The exterior features light blue siding with multiple windows and a door that opens to the inviting outdoor space. Stone walkways lead through the landscape.
Tiny home in Chapel Hill
4.95 out of 5 average rating, 214 reviews

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!

Top Guest favourite
A charming red cabin is framed by lush green trees, with soft golden sunlight illuminating the grassy lawn. A gravel driveway leads toward the welcoming porch, set amidst a serene rural landscape that features a fenced pasture in the background.
Cottage in Pittsboro
5 out of 5 average rating, 124 reviews

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.

Top Guest favourite
Home in Pittsboro
4.99 out of 5 average rating, 364 reviews

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.

Popular amenities for Pittsboro holiday rentals

When is the best time to visit Pittsboro?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price$168 AUD$168 AUD$168 AUD$167 AUD$168 AUD$168 AUD$168 AUD$168 AUD$168 AUD$182 AUD$182 AUD$182 AUD
Avg. temp5°C6°C10°C15°C19°C23°C25°C25°C21°C15°C10°C6°C

Frequently Asked Questions

  • How much does it cost to stay in house rentals in Pittsboro?

    Experience the best of Pittsboro with our house rentals, starting at about $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there vacation rentals with a dedicated workspace in Pittsboro?

    Yes! Work meets play with ease at over 20 vacation rentals in Pittsboro featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there family-friendly vacation rentals in Pittsboro?

    Pittsboro has more than 10 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Are there pet-friendly vacation rentals in Pittsboro?

    Four-legged friends are welcome in Pittsboro. Choose from more than 10 vacation rentals for guests traveling with pets.

  • Do house rentals in Pittsboro have air conditioning?

    Absolutely! We offer over 10 house rentals with air conditioning in Pittsboro. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Pittsboro have wifi?

    Absolutely! We offer over 10 house rentals with wifi in Pittsboro. Enjoy a tailored experience with all the comforts you desire.

Quick stats about holiday rentals in Pittsboro

  • Total holiday rentals

    Explore 30 holiday rentals in Pittsboro

  • Nightly prices starting at

    Pittsboro holiday rentals start at $56 AUD per night before taxes and fees

  • Verified guest reviews

    Over 2,140 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    30 of Pittsboro holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Gym, BBQ grill and Laptop-friendly workspace across Pittsboro rentals

  • 4.9 Average rating

    Pittsboro stays are highly rated by guests—averaging 4.9 out of 5!