
Holiday houses in Pittsboro
Find and book unique accommodation on Airbnb
Top-rated holiday rentals in Pittsboro
Guests agree: these stays are highly rated for location, cleanliness and more.

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.

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.

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.

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!

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

"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.

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.

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!

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.

Best location! Clean, beautiful, walkable cottage.
Newly updated, bright, clean studio guest house Located in a highly desirable neighborhood, near several parks and walking trails, restaurants, coffee shops, Weaver Street Co-op Market, village green with outdoor movie screen, a gym, and just about anything you could need. Bus stops nearby take you just about anywhere you need to go, run frequently, and are free! Very close to UNC, and hospitals, downtown Carrboro and downtown Chapel Hill.

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.

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!
Popular amenities for Pittsboro holiday rentals
Other great holiday rentals in Pittsboro

Duke Forest Hideaway

Tiny home on private 35 acre farm.

The Sacred Cedar, near Chapel Hill & UNC

Yurt at Kinfolk Gardens

Country Oasis on 24 Acres - Walk to River & Lake

Historic & Charming Pittsboro Home w/ Fireplaces

Sunny, private, clean and green!

Cozy Beehive Treehouse
When is the best time to visit Pittsboro?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $179 AUD | $179 AUD | $179 AUD | $177 AUD | $179 AUD | $179 AUD | $179 AUD | $179 AUD | $179 AUD | $194 AUD | $194 AUD | $249 AUD |
| Avg. temp | 5°C | 6°C | 10°C | 15°C | 19°C | 23°C | 25°C | 25°C | 21°C | 15°C | 10°C | 6°C |
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 $89 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!
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- Duke University
- PNC Arena
- North Carolina Zoo
- Wet'n Wild Emerald Pointe Water Park
- Pinehurst Resort
- Raven Rock State Park
- Durham Bulls Athletic Park
- Pine Needles Lodge and Golf Club
- World Golf Village
- Frankie's Fun Park
- Greensboro Science Center
- Carolina Theatre
- American Tobacco Campus
- North Carolina Museum of Art
- Lake Johnson Park
- North Carolina Museum of Natural Sciences
- Eno River State Park
- William B. Umstead State Park
- North Carolina Museum of History
- Sarah P. Duke Gardens
- Durham Farmers' Market
- Dorothea Dix Park
- North Carolina Central University
- International Civil Rights Center & Museum




