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.

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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

Jan 3 – 10

G$22,190 GYD per night

Guest favorite

Apartment in Pittsboro

4.97 out of 5 average rating, 230 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.

Jan 3 – 10

G$25,576 GYD per night

Guest favorite

Cabin in Hillsborough

4.99 out of 5 average rating, 254 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 22 – 29

G$29,908 GYD per night

Guest favorite

Guesthouse in Saxapahaw

4.92 out of 5 average rating, 698 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.

Mar 12 – 19

G$24,625 GYD per night

Guest favorite

Home in Pittsboro

4.95 out of 5 average rating, 131 reviews

A Gem of a House by the River near Chapel Hill

This serene home on a half-acre is only minutes away from local landmarks and yet offers a haven for those needing a place to reset or spend time with family and friends. Sip tea on the porches, sit under the grand oak tree, and enjoy the original wood floors, modern kitchen, beautiful furnishings and art work, comfy beds, and all the conveniences for an easeful stay. Located in the charming village of Bynum, this unique home offers the chance to roll with the river for a while.

Jul 10 – 17

G$35,055 GYD per night

Guest favorite

Tiny home in Chapel Hill

4.93 out of 5 average rating, 605 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 18 – 25

G$23,422 GYD per night

Guest favorite

Farm stay in Chapel Hill

4.98 out of 5 average rating, 479 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

Jun 16 – 23

G$27,506 GYD per night

Guest favorite

Bungalow in Pittsboro

4.94 out of 5 average rating, 145 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!

Oct 3 – 10

G$21,787 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.

Jun 28 – Jul 5

G$17,334 GYD per night

Guest favorite

Farm stay in Chapel Hill

4.97 out of 5 average rating, 135 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$32,119 GYD per night

Guest favorite

Bungalow in Pittsboro

4.9 out of 5 average rating, 112 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!

Sep 15 – 22

G$27,197 GYD per night

Guest favorite

Home in Pittsboro

4.99 out of 5 average rating, 277 reviews

Second Home in Pittsboro, NC

This newly remodeled home is on 4 wooded acres in Pittsboro. It is one mile from Chatham Park, and close to the downtown shops and restaurants. It is convenient to drive to Jordan Lake, Fearrington Village, Chaple Hill, Apex, and Cary. Chatham County is one of the fastest growing in the state, but Pittsboro retains it's historic and eclectic roots. We are pet-friendly, with a fenced in backyard.

Nov 15 – 22

G$23,197 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, 294 reviews

Country Retreat. Close to Town!

Feb 22 – Mar 1

G$28,378 GYD per night

Guest favorite

Guest suite in Mebane

5.0 out of 5 average rating, 142 reviews

Gorgeous Retreat - Close to CH/Carrboro/Saxapahaw

Jul 16 – 23

G$19,908 GYD per night

Guest favorite

Farm stay in Snow Camp

4.91 out of 5 average rating, 151 reviews

Guest House at Dinner Bell Farm Stay

Oct 2 – 9

G$19,455 GYD per night

Guest favorite

Guesthouse in Cedar Grove

4.95 out of 5 average rating, 244 reviews

Private Lake Retreat

Nov 6 – 13

G$27,342 GYD per night

Guest favorite

Guesthouse in Apex

4.92 out of 5 average rating, 345 reviews

Country place close to all Triangle locations

Jun 14 – 21

G$19,414 GYD per night

Superhost

Guest suite in Chapel Hill

4.85 out of 5 average rating, 346 reviews

Art, Beauty, Nature: A Woodland Retreat

Jan 27 – Feb 3

G$25,875 GYD per night

Guest favorite

Guest suite in Chapel Hill

4.89 out of 5 average rating, 561 reviews

Modern 1 Bedroom Suite - Close to UNC/Downtown

Mar 18 – 25

G$20,941 GYD per night

Guest favorite

Tiny home in Chapel Hill

4.94 out of 5 average rating, 143 reviews

Cozy Art Cabin among organic gardens near UNC/Duke

Jul 25 – Aug 1

G$21,166 GYD per night

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Other great vacation rentals in Pittsboro

Guest favorite

Home in Pittsboro

5.0 out of 5 average rating, 13 reviews

Sunny and clean, green certified, fenced yard

May 6 – 13

G$26,849 GYD per night

Guest favorite

Treehouse in Pittsboro

5.0 out of 5 average rating, 5 reviews

NEW Beehive Tree House Retreat

Jun 4 – 11

G$32,706 GYD per night

Guest favorite

Guesthouse in Pittsboro

4.95 out of 5 average rating, 21 reviews

The Sacred Cedar

Jul 30 – Aug 6

G$29,804 GYD per night

Guest favorite

Bungalow in Pittsboro

4.92 out of 5 average rating, 49 reviews

Modern Cottage in the Pines, 15min to Chapel Hill

Oct 23 – 30

G$35,034 GYD per night

Guest favorite

Home in Pittsboro

5.0 out of 5 average rating, 24 reviews

Relaxing Getaway Apartment

Jul 10 – 17

G$24,002 GYD per night

Guest favorite

Apartment in Fearrington

4.94 out of 5 average rating, 97 reviews

Awesome Fearrington Place - a family tradition.

Feb 9 – 16

G$26,997 GYD per night

Guest favorite

Loft in Chatham County

5.0 out of 5 average rating, 21 reviews

1 Bed 1 Bath Modern Loft Close to UNC/Duke

Aug 20 – 27

G$26,826 GYD per night

Guest favorite

Tiny home in Chapel Hill

4.88 out of 5 average rating, 41 reviews

Cozy Tiny house near UNC

Jun 6 – 13

G$19,097 GYD per night

Show all

Quick stats about vacation rentals in Pittsboro

Total rentals
20 properties
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Pet-friendly rentals
10 properties allow pets
Family-friendly rentals
10 properties are a good fit for families
Total number of reviews
1.3K reviews
Nightly prices starting at
G$12,509 GYD before taxes and fees

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Pittsboro?
Yes! Work meets play with ease at over 10 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 $60 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 wifi, over 10 homes with air conditioning, 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.

Pittsboro places to stay

Top-rated places to stay in Pittsboro

Vacation rentals for every style

Hotels

Unique stays

Homes

Popular amenities for Pittsboro places to stay

Stay near Pittsboro's top sights

Other great vacation rentals in Pittsboro

Cottage in Chapel Hill

Guest suite in Mebane

Farm stay in Snow Camp

Guesthouse in Cedar Grove

Guesthouse in Apex

Guest suite in Chapel Hill

Guest suite in Chapel Hill

Tiny home in Chapel Hill

Other great vacation rentals in Pittsboro

Home in Pittsboro

Treehouse in Pittsboro

Guesthouse in Pittsboro

Bungalow in Pittsboro

Home in Pittsboro

Apartment in Fearrington

Loft in Chatham County

Tiny home in Chapel Hill

Quick stats about vacation rentals in Pittsboro

Total rentals

Rentals with dedicated workspaces

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Pittsboro?

How much does it cost to stay in house rentals in Pittsboro?

Do house rentals in Pittsboro have wifi?

Are there pet-friendly vacation rentals in Pittsboro?

What are the most popular amenities for House Rentals in Pittsboro?

Are there family-friendly vacation rentals in Pittsboro?

Destinations to explore