Pittsboro places to stay

Book unique places to stay, houses, and more on Airbnb

Top-rated places to stay in Pittsboro

Guests agree: these places to stay are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

Guest favorite

Shipping container in Pittsboro

4.93 out of 5 average rating, 136 reviews

Quirky Fun B&B: Tree House Unit

This unit is a refurbished container building built by an architect professor at UNC-C for a traveling art exhibit A space efficient room (8ftx8ft) with a tall, airy, ceiling, full size bed, private bath, micromini fridge (holds the equivalent of six 12oz cans), pod coffee maker, and smart TV for streaming Pets under 20 lbs. allowed due to size The deck seats 2 overlooking the art-filled gardens Rates are SINGLE OCCUPANCY ONLY An additional $25 per person per night per additional guest applies

Jul 9 – 16

G$21,021 GYD per night

Guest favorite

Home in Pittsboro

4.96 out of 5 average rating, 134 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.

Jul 30 – Aug 6

G$35,081 GYD per night

Guest favorite

Apartment in Pittsboro

4.97 out of 5 average rating, 231 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.

Aug 18 – 25

G$25,595 GYD per night

Guest favorite

Guesthouse in Saxapahaw

4.92 out of 5 average rating, 699 reviews

The Yurt at Frog Pond Farm

Our yurt (30' dia.) is rustic, beautiful, quiet, in deep woods with deck overlooking pond. Great for couples, small families (not childproof). Includes hot tub & Poetry Walk. Beds are futons. It's warm June-Aug. (no A/C, plenty fans), but way cooler than the city. It's cold Nov.-March (wood stove heat). Mini-fridge & microwave (no kitchen/plumbing). Bath-house is 2-min. walk (toilet, sink, shower). Two minutes to Saxapahaw. Read description for more info. SERIOUSLY NO PARTIES. And no dogs.

Aug 21 – 28

G$25,714 GYD per night

Guest favorite

Cabin in Hillsborough

4.99 out of 5 average rating, 256 reviews

Artist's Studio

Until recently 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, homemade granola, 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.

Jun 16 – 23

G$29,930 GYD per night

Guest favorite

Tiny home in Chapel Hill

4.93 out of 5 average rating, 610 reviews

Chic Modern Tiny House Nestled in the Trees

This 240 sq ft tiny house is situated on a serene 5 acre wooded property. Its a short drive to Hillsborough (10 min), Chapel Hill (15) and Durham (15). I wanted to create a space where guests can take time to rest and reset. Stylish decor, art-filled walls, and a full list of amenities make for a unique and cozy experience of home away from home. Take a step outside and you'll be surrounded by old hardwood trees and the soothing sounds of nature that make life here so peaceful

Jun 14 – 21

G$23,439 GYD per night

Guest favorite

Farm stay in Chapel Hill

4.98 out of 5 average rating, 482 reviews

Carriage House-32 Acre Wooded Lot & Trails & Pond

-private 2015 carriage house in Chapel Hill; less than 2 miles from I-40 -less than 8 miles from UNC; less than 20 minutes from Duke -2 bedrooms with queen, 2 twins & a trundle bed -32 acre private wooded lot with 2 mi. of trails with stocked pond -open floor plan of 1000 sq.ft. -fully stocked kitchen -high speed wireless internet with YouTube TV; ESPN -on-site washer and dryer (free) -stairs from ground to apartment -4 vehicles parking; small moving truck too -outdoor grill

Jul 22 – 29

G$28,566 GYD per night

Guest favorite

Bungalow in Pittsboro

4.95 out of 5 average rating, 148 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!

Aug 9 – 16

G$22,102 GYD per night

Guest favorite

Guesthouse in Chapel Hill

4.96 out of 5 average rating, 340 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.

Jul 27 – Aug 3

G$17,347 GYD per night

Guest favorite

Farm stay in Chapel Hill

4.97 out of 5 average rating, 136 reviews

The Homestead, a 1927 Renovated Farmhouse

This newly renovated farmhouse sits nestled between a working dairy farm and 5 acres of woods. The front porch view includes pastures, fields and Collins Mountain. This well kept rental is perfect for those looking for a quiet getaway or a unique stay near the towns of Saxapahaw (9 miles away) and Chapel Hill/Carrboro (12 miles away). Also convenient to Pittsboro and Mebane. The beautiful Haw River is nearby with fishing, kayaking and hiking trails.

Aug 17 – 24

G$32,142 GYD per night

Guest favorite

Farm stay in Snow Camp

4.91 out of 5 average rating, 152 reviews

Guest House at Dinner Bell Farm Stay

Enjoy a comfy retreat on our beautiful organic farm – yet you will be only a short drive from the village of Saxapahaw and a wide variety of sites to see and activities to do all around us. Relax and enjoy our 40 acres of pastures, forest, and gardens. Sit under the huge oak tree outside your porch, nap or daydream in the hammock, watch the sunset over the fields and the stars come out, tell stories around the fire pit.

Jun 18 – 25

G$19,469 GYD per night

Guest favorite

Bungalow in Pittsboro

4.9 out of 5 average rating, 115 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!

Mar 24 – 31

G$30,448 GYD per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Pittsboro places to stay

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Stay near Pittsboro's top sights

S & T's Soda Shoppe9 locals recommend

Virlie's Grill9 locals recommend

Al's Diner4 locals recommend

Elizabeth's Pizza & Italian Restaurant4 locals recommend

Carolina Brewery & Grill6 locals recommend

Pittsboro Roadhouse5 locals recommend

Other great vacation rentals in Pittsboro

Guest favorite

Cottage in Chapel Hill

4.9 out of 5 average rating, 296 reviews

Country Retreat. Close to Town!

Aug 20 – 27

G$30,057 GYD per night

Guest favorite

Apartment in Chapel Hill

4.96 out of 5 average rating, 107 reviews

Treehouse in the Woods

Aug 26 – Sep 2

G$22,758 GYD per night

Guest favorite

Guest suite in Chapel Hill

4.93 out of 5 average rating, 215 reviews

Private retreat close to Chapel Hill!

Oct 9 – 16

G$19,197 GYD per night

Guest favorite

Guesthouse in Hillsborough

4.97 out of 5 average rating, 194 reviews

CFCB cabin retreat minutes from Duke, NCCU, & UNC

Apr 29 – May 6

G$24,966 GYD per night

Guest favorite

Cabin in Pittsboro

4.96 out of 5 average rating, 26 reviews

Peaceful retreat in Fearrington Village

Sep 21 – 28

G$25,601 GYD per night

Guest favorite