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.

Guest favorite

Shipping container in Pittsboro

4.92 out of 5 average rating, 131 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

Sep 23 – 30

$88 per night
Guest favorite

Apartment in Pittsboro

4.97 out of 5 average rating, 226 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.

Jun 10 – 17

$108 per night
Superhost

Guest suite in Chapel Hill

4.85 out of 5 average rating, 342 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.

Dec 18 – 25

$134 per night

Popular amenities for Pittsboro places to stay

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

Guesthouse in Cedar Grove

4.95 out of 5 average rating, 238 reviews

Private Lake Retreat

Dec 3 – 10

$108 per night
Guest favorite

Home in Chapel Hill

4.95 out of 5 average rating, 173 reviews

Unique, bright and airy two bedroom

Feb 9 – 16

$104 per night
Guest favorite

Cottage in Chapel Hill

4.9 out of 5 average rating, 293 reviews

Country Retreat. Close to Town!

Jan 13 – 20

$118 per night
Guest favorite

Apartment in Chapel Hill

4.84 out of 5 average rating, 232 reviews

The Cozy Bungalow - Noted Historic Home near UNC!

Jun 19 – 26

$106 per night
Guest favorite

Tiny home in Chapel Hill

4.94 out of 5 average rating, 142 reviews

Cozy Art Cabin among organic gardens near UNC/Duke

Nov 16 – 23

$76 per night
Guest favorite

Guest suite in Mebane

5.0 out of 5 average rating, 140 reviews

Gorgeous Retreat - Close to CH/Carrboro/Saxapahaw

Jun 28 – Jul 5

$88 per night
Guest favorite

Farm stay in Chapel Hill

4.98 out of 5 average rating, 476 reviews

Carriage House-32 Acre Wooded Lot & Trails & Pond

Jun 15 – 22

$115 per night
Guest favorite

Home in Chapel Hill

4.92 out of 5 average rating, 262 reviews

Grandma’s House

Aug 28 – Sep 4

$99 per night
Guest favorite

Guesthouse in Apex

4.92 out of 5 average rating, 337 reviews

Country place close to all Triangle locations

May 26 – Jun 2

$81 per night
Guest favorite

Farm stay in Mebane

4.94 out of 5 average rating, 146 reviews

Little Blue Farm House

Jan 23 – 30

$84 per night
Guest favorite

Guest suite in Chapel Hill

4.93 out of 5 average rating, 200 reviews

Private retreat close to Chapel Hill!

Sep 8 – 15

$80 per night
Guest favorite

Guest suite in Chapel Hill

4.89 out of 5 average rating, 552 reviews

Modern 1 Bedroom Suite - Close to UNC/Downtown

Dec 16 – 23

$84 per night

Other great vacation rentals in Pittsboro

Guest favorite

Apartment in Pittsboro

5.0 out of 5 average rating, 24 reviews

Forest Refuge Retreat Apartment

May 27 – Jun 3

$77 per night
Guest favorite

Home in Pittsboro

5.0 out of 5 average rating, 13 reviews

Spacious, sunny and clean - green certified

Apr 14 – 21

$105 per night
Guest favorite

Home in Pittsboro

5.0 out of 5 average rating, 21 reviews

Relaxing Getaway Apartment

Jul 7 – 14

$100 per night
Guest favorite

Cabin in Pittsboro

4.96 out of 5 average rating, 23 reviews

Peaceful retreat in Fearrington Village

Jul 17 – 24

$106 per night
Guest favorite

Bungalow in Pittsboro

4.91 out of 5 average rating, 46 reviews

Modern Cottage in the Pines, 15min to Chapel Hill

Nov 18 – 25

$135 per night
Guest favorite

Home in Pittsboro

4.94 out of 5 average rating, 16 reviews

"Hawks Nest"

Apr 21 – 28

$94 per night
Guest favorite

Cottage in Pittsboro

5.0 out of 5 average rating, 65 reviews

Newly renovated cabin on rural heritage farm.

Nov 8 – 15

$105 per night
Guest favorite

Treehouse in Pittsboro

4.88 out of 5 average rating, 17 reviews

New H2O Oasis Tree House

Dec 12 – 19

$138 per night
Guest favorite

Loft in Chatham County

5.0 out of 5 average rating, 20 reviews

1 Bed 1 Bath Modern Loft Close to UNC/Duke

Jun 29 – Jul 6

$108 per night
Guest favorite

Apartment in Fearrington

4.94 out of 5 average rating, 96 reviews

Awesome Fearrington Place - a family tradition.

Mar 22 – 29

$113 per night
Guest favorite

Farm stay in Siler City

5.0 out of 5 average rating, 69 reviews

Lovely farm cabin experience

Jun 25 – Jul 2

$115 per night
Superhost

Home in New Hill

4.86 out of 5 average rating, 36 reviews

Jordan Lake Bungalow

Apr 14 – 19

$98 per night

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

1.2K reviews

Nightly prices starting at

$60 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.

Destinations to explore