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Pittsboro places to stay

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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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Shipping container in Pittsboro

4.92 out of 5 average rating, 156 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

Home in Pittsboro

4.95 out of 5 average rating, 151 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.

Rental unit in Pittsboro

4.98 out of 5 average rating, 245 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.

Guesthouse in Saxapahaw

4.92 out of 5 average rating, 737 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). Parking and the bath-house are 2-min. walks (toilet, sink, shower). Two minutes to Saxapahaw. Read description for more info. NO PARTIES. No dogs.

Guest suite in Chapel Hill

4.86 out of 5 average rating, 381 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.

Farm stay in Pittsboro

4.98 out of 5 average rating, 179 reviews

Guest House @ Mission Farm, quiet, farm setting

18 minutes to down town Chapel Hill/Franklin Street or historic & quaint downtown Pittsboro. Relax in a beautiful farm house on 10 acres near the Haw River with rolling pastures, woods, chickens, ducks, cows and and pond views. GREAT couple weekend getaway, those traveling to UNC/Duke sporting events, families with kids. Will consider single night weekend stays within 4 weeks requested night. The Cottage at Mission Farm is now also available for rent for additional 4 people

Rental unit in Fearrington

4.94 out of 5 average rating, 112 reviews

Awesome Fearrington Place - a family tradition.

Tradition continues. When my parents, Audrey and Elmo Jones, moved to Fearrington in 1984, they added a guest apartment over the garage where many people discovering the Village stayed, most new to my parents. In 1993, my boys and I moved into the apartment after their father died. I now live in the main house and continue the tradition of sharing this unique space with friends, family and travelers. I look forward to welcoming you as you help us honor my Grandmama and Poppa.

Tiny home in Chapel Hill

4.93 out of 5 average rating, 106 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 but additional fee required, message for details.

Bungalow in Pittsboro

4.96 out of 5 average rating, 181 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!

Guesthouse in Chapel Hill

4.96 out of 5 average rating, 362 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.

Bungalow in Pittsboro

4.88 out of 5 average rating, 148 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!

Home in Pittsboro

4.99 out of 5 average rating, 317 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.

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Popular amenities for Pittsboro places to stay

Laptop-friendly workspace

Air conditioning

Stay near Pittsboro's top sights

The City Tap18 locals recommend

Chatham Marketplace15 locals recommend

French Connections12 locals recommend

Small B&B Cafe10 locals recommend

Postal Fish Company9 locals recommend

S & T's Soda Shoppe9 locals recommend

Other great vacation rentals in Pittsboro

Loft in Chatham County

5 out of 5 average rating, 27 reviews

1 Bed 1 Bath Modern Loft Close to UNC/Duke

Cottage in Pittsboro

4.93 out of 5 average rating, 54 reviews

Cozy Wooded barndominium near Chapel Hill

Home in Pittsboro

5 out of 5 average rating, 25 reviews

On 24 acres, a private, comfy home, DeerField.

Bungalow in Pittsboro

4.94 out of 5 average rating, 66 reviews

Modern Cottage in the Pines

Cottage in Siler City

5 out of 5 average rating, 52 reviews

Cedar Serenity Guest House

Rental unit in Chapel Hill

4.97 out of 5 average rating, 34 reviews

Park @ the Hill-5 miles to UNC

Home in Pittsboro

4.98 out of 5 average rating, 53 reviews

Home in Pittsboro

Home in Pittsboro

5 out of 5 average rating, 25 reviews

Juniper Cottage in the Grove

Quick stats about vacation rentals in Pittsboro

Total rentals
20 properties
Nightly prices starting at
$60 before taxes and fees
Total number of reviews
1.6K reviews
Family-friendly rentals
10 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace

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 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.

Destinations to explore