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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Guest favourite
A modern studio features a comfortable gray couch adorned with decorative pillows. A wooden counter is accompanied by three metal stools. The kitchen, equipped with essential appliances, is visible in the background, with ample natural light flowing in from the adjacent area.
Guest suite in Carrboro
4.88 out of 5 average rating, 186 reviews

Carrboro/Chapel Hill/UNC Studio

This stylish studio is a 5 min drive to downtown Carrboro and Chapel Hill. Weatherhill Townhomes are secluded and have easy parking. There is a king-sized bed for maximum comfort, and the couch can sleep one additional guest if needed. Enjoy the kitchen and having a bathroom all to yourself! This private basement unit overlooks the forest, which provides a lovely view any time of year. To that end, remember to bring a laptop if you want screen time (no tv here, but there is private internet!).

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
4.98 out of 5 average rating, 282 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 warm dining area features a wooden table surrounded by four chairs, with a decorative rug beneath. A modern kitchen is visible in the background, showcasing stainless steel appliances and a cozy fireplace nestled in a green accent wall.
Home in Pittsboro
4.95 out of 5 average rating, 173 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 private, covered deck features two simple chairs positioned around a wooden table. Natural light filters through the overhead structure, enhancing the view of the surrounding wooded area. A pathway leads away from the deck, inviting exploration of the tranquil outdoors.
Guest suite in Chapel Hill
4.87 out of 5 average rating, 442 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
Guest suite in Chapel Hill
4.94 out of 5 average rating, 111 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
4.91 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, 189 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
The charming bungalow features a red metal roof and a welcoming front porch with two rocking chairs and yellow accents. Flower pots and decorative elements adorn the porch, while large windows provide natural light to the interior. A brick walkway leads to the entrance.
Bungalow in Pittsboro
4.95 out of 5 average rating, 253 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
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).

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, 208 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, 117 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.

Guest favourite
A vibrant neon sign displaying the words 'good vibes' is mounted against a textured green wall, creating a lively focal point. The wall features a lush appearance, enhancing the playful atmosphere of the space.
Bungalow in Pittsboro
4.89 out of 5 average rating, 198 reviews

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!

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 air conditioning, over 10 homes with wifi, 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 $84 AUD per night before taxes and fees

  • Verified guest reviews

    Over 2,060 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!