Holiday houses in Pittsboro

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Top-rated holiday rentals in Pittsboro

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Guest favourite

Home in Pittsboro

4.94 out of 5 average rating, 160 reviews

A Gem of a House by the River near Chapel Hill

Escape to tranquility at this charming half-acre oasis, minutes from local gems yet a world away. Sip tea on the porches overlooking lush gardens. Relax under the grand oak's dappled shade. Step inside to original wood floors, a modern kitchen, cozy beds, and artistic touches throughout. Whether resetting solo or gathering loved ones, this unique Bynum village retreat envelops you in calm. Stroll to the riverbank or through the charming neighborhood and let the gentle currents soothe your soul.

Top Guest favourite

Apartment in Pittsboro

4.97 out of 5 average rating, 261 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.

Superhost

Guest suite in Chapel Hill

4.87 out of 5 average rating, 418 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

Shipping container in Pittsboro

4.92 out of 5 average rating, 170 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

Home in Chapel Hill

5 out of 5 average rating, 142 reviews

White Oak Hill, minutes to UNC & Duke

Have everything you need for a hassle-free Chapel Hill/Carrboro retreat at this perfectly appointed home just 6 miles west of the city. Newly remodeled to please with luxury finishes inside and out, this vacation rental is highlighted by serene and beautiful country views from every window. This spacious layout sleeps 10 with 4 bedrooms, 2 full bathrooms, 1 half bath, 2 living rooms, bar seating and separate dining room. Foodies will love cooking in the fully equipped gourmet kitchen!

Top Guest favourite

Townhouse in Chapel Hill

5 out of 5 average rating, 114 reviews

Anna Belle's Retreat - Belle (Side B)

This renovated duplex offers tranquility, style and comfort. Situated in the North Chatham area, we are just a short drive to Chapel Hill and Pittsboro. Jordan Lake and Haw River are also close by. Nestled in the pines yet within walking distance to nearby shopping, you'll experience the peacefulness of being in the country with the conveniences of being in the city. Enjoy the private screened porch with adjoining patio and grilling area. Need more space? Unit A is also available.

Top Guest favourite

Tiny home in Efland

5 out of 5 average rating, 250 reviews

Timberwood Tiny Home

Timberwood Tiny Home is a place to rest your head & heart in Efland, North Carolina. The peaceful retreat, designed for adults only, is down a country road approximately 10-minutes from downtown Hillsborough. The 200 square foot tiny home is on a private corner of 8-acres shared with our main house. It features Scandinavian-style details, two beds, a spacious porch, abundant natural light, a wood-fired hot tub, barrel sauna, cold plunge, and much more. @timberwoodtinyhome

Top Guest favourite

Bungalow in Pittsboro

4.95 out of 5 average rating, 210 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!

Superhost

Home in Chapel Hill

4.9 out of 5 average rating, 113 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

Tiny home in Chapel Hill

4.93 out of 5 average rating, 161 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

Cottage in Pittsboro

5 out of 5 average rating, 99 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

Bungalow in Pittsboro

4.89 out of 5 average rating, 170 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!