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, 276 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 calm lakeside view is presented from the porch, showcasing the serene water reflecting the vibrant sky. Lush trees line the opposite bank, complementing the peaceful atmosphere of the environment, with glimpses of nearby cottages adding to the charming scenery.
Home in Sanford
4.97 out of 5 average rating, 109 reviews

Cottage at Water's Edge - a cozy stay on the lake.

Immerse yourself in the serene beauty of the Carolina pines as you unwind in this cozy cottage on the water's edge. This hidden gem is ideally situated between major urban centers, yet offers a peaceful retreat from the hustle and bustle. The cottage on the lake has been fully renovated and enhanced with modern amenities and stylish touches. During your stay, you can explore the lake on a kayak or a canoe, enjoy some fishing, or simply savor the tranquil views from the porch swing or hammock.

Top Guest favourite
A bright interior showcases a spacious dining area with a wooden table and white chairs, complemented by floor-to-ceiling windows. The green accent wall offers a natural touch, while a wooden ladder leads to a loft space above. Light-colored wood flooring enhances the open feel.
Tiny home in Franklin-Rosemary
4.99 out of 5 average rating, 113 reviews

The Chapel Hill Forest House

Book this incredible tiny house for the perfect romantic getaway in the heart of Chapel Hill! It sits in a private forest full of wildlife but is only a 5-minute walk to Franklin Street and the UNC campus. Enjoy amazing views from the floor-to-ceiling windows of foxes and deer playing on the lawn. Lounge on the wall-to-wall hammock as you gaze at the trees through the skylights. Unwind with a movie in bed played on our massive projector. There's nothing like this anywhere in the Triangle!

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, 183 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

Guest favourite
A charming cabin features a front porch with two chairs and a small table. The exterior is painted in calming green tones, surrounded by lush trees. A door with a window provides access, while a lantern and potted plants add subtle details to the cozy environment.
Farm stay in Hillsborough
4.9 out of 5 average rating, 176 reviews

Cozy Cabin in the Countryside

Enjoy a cozy cabin with internet, ac/heat, kitchenette with fridge and microwave. Please note there is no water in the cabin and shower and toilet are located in the bathhouse just a few steps away. This comfortable Cabin has very easy quick access to all amenities including the showerhouse, picnic areas, lawn games, outdoor kitchen. Hottub is open. Property is within minutes of downtown Chapel Hill & Hillsborough, Raleigh, Durham are 20-30 minutes away. No Smoking or Vaping in Cabins

Top Guest favourite
A petite building constructed from weathered wood stands amidst lush greenery. Unique arched windows and a rustic roof contribute to its character. Soft lighting from within casts a warm glow, creating an inviting scene as the vibrant foliage frames the structure.
Cabin in Hillsborough
4.99 out of 5 average rating, 308 reviews

Artist's Studio

Originally the studio of a visual artist (long ago garden illustrator for The New York Times), this petite building is completely private. Firm queen bed. Mix of antiques and artisanal built-ins. Radiant heat. AC. Mini fridge and microwave, electric kettle, Chemex coffee maker and French Press, excellent wifi. Unique space in one of the best country neighborhoods around. 6.5 miles to Hillsborough healthy grocery store, 8 to Carrboro/Chapel Hill, 18 to Durham. Serene pond and grounds.

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, 178 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, 161 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, 238 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
The exterior of the studio apartment is shown, featuring a wooden deck with a railing. A stack of firewood is arranged nearby. The entrance is marked by glass doors, while greenery surrounds the space, creating a natural setting.
Guesthouse in Chapel Hill
4.96 out of 5 average rating, 395 reviews

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.

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, 107 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
4.91 out of 5 average rating, 126 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.

Popular amenities for Pittsboro holiday rentals

When is the best time to visit Pittsboro?

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Avg. price$211 NZD$211 NZD$211 NZD$209 NZD$211 NZD$211 NZD$211 NZD$211 NZD$211 NZD$229 NZD$229 NZD$294 NZD
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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 air conditioning?

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

  • 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.

  • 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.

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 $53 NZD 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!