Holiday houses in Pittsboro

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Top-rated holiday rentals in Pittsboro

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

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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 Pittsboro
4.97 out of 5 average rating, 279 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.

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, 171 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 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, 437 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.

Superhost
A well-appointed sleeping area features a spacious bed covered with a soft blanket, complemented by two nightstands. A cozy brown loveseat and a desk are positioned nearby, with a round mirror reflecting the warm light from a lamp. Natural light enters through a window, adorned with blue curtains.
Guest suite in Chapel Hill
4.94 out of 5 average rating, 110 reviews

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!

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
4.92 out of 5 average rating, 189 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, 184 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.

Top Guest favourite
A spacious gray craftsman-style home is surrounded by tall trees and landscaped gardens. The front yard features a mix of grass and shrubs, creating an inviting entrance. Sunlight casts long shadows, enhancing the serenity of the peaceful outdoor setting.
Guest suite in Mebane
5 out of 5 average rating, 165 reviews

Gorgeous Retreat - Close to CH/Carrboro/Saxapahaw

Welcome to our cozy craftsman guest suite! Private and peaceful - we're situated on 5 acres close to Carrboro/Chapel Hill (13 mi), UNC Hospitals (15 mi), Elon (20 mi), and the charming Village of Saxapahaw (5 mi). The guest suite is a spacious 500 sq ft with private entrance, full kitchen and bath, bedroom, and living area. With views into the woods and garden, it's a beautiful spot to get away, relax, and enjoy nature. Great for couples and solo travelers alike.

Top Guest favourite
A charming bungalow is illuminated softly in the evening, showcasing a welcoming red door and large front porch. Surrounding greenery enhances the home's rustic appeal, while a small detached structure is visible in the yard, creating a cozy, inviting atmosphere.
Bungalow in Pittsboro
4.95 out of 5 average rating, 247 reviews

Whimsy Cottage Close to Everything in Pittsboro

Charming 2-bedroom, 1-bathroom, Boho Elegant 1927 Bungalow in the heart of Pittsboro West. Step off the large front porch and head across the street to a local craft brewery, shopping, a delicious bakery serving breakfast and lunch and Chatham County Community College with a public library and paved walking trail. Walking distance to great bars, shops and restaurants in downtown Pittsboro. Whimsy on West is the perfect home away from home for any reason!

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, 110 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 bedroom + private loft with 2 beds. (loft accessed by stair ladder).

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, 130 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, 200 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, 115 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.

Popular amenities for Pittsboro holiday rentals

When is the best time to visit Pittsboro?

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Frequently Asked Questions

  • 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.

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

    Experience the best of Pittsboro with our house rentals, starting at about $30 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • 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.

  • 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.

  • What are the most popular amenities for House Rentals in Pittsboro?

    Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with wifi, over 10 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • 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.

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 $45 AUD per night before taxes and fees

  • Verified guest reviews

    Over 1,960 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!