Holiday houses in Pittsboro

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Top-rated holiday rentals in Pittsboro

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Guest favourite

Shipping container in Pittsboro

4.93 out of 5 average rating, 134 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

12–19 Sep

$208 NZD per night

Guest favourite

Apartment in Pittsboro

4.97 out of 5 average rating, 228 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.

11–18 Dec

$229 NZD per night

Guest favourite

Home in Pittsboro

5.0 out of 5 average rating, 13 reviews

Sunny and clean, green certified, fenced yard

This adobe style green home is light-filled, spacious, regularly deep cleaned and offers a nicely equipped kitchen! One level entry/no steps. Fenced yard for well behaved kids and dogs! Easy walk to downtown, library, disc golf, trails, eateries and breweries. Tucked in an established neighborhood on the edge of the woods. Work station, printer and fast internet. Comfortable 1 BDR with queen bed plus full size bed setup in parlor on request. Relax and welcome to the West End of Pittsboro!

28 Apr – 5 May

$253 NZD per night

Guest favourite

Guesthouse in Saxapahaw

4.92 out of 5 average rating, 693 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.

14–21 Nov

$220 NZD per night

Guest favourite

Home in Pittsboro

4.95 out of 5 average rating, 129 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.

28 May – 4 Jun

$341 NZD per night

Guest favourite

Tiny home in Chapel Hill

4.93 out of 5 average rating, 600 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

3–10 Jun

$212 NZD per night

Guest favourite

Guest suite in Mebane

5.0 out of 5 average rating, 142 reviews

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.

8–15 Aug

$179 NZD per night

Guest favourite

Bungalow in Pittsboro

4.94 out of 5 average rating, 144 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!

4–11 Sep

$210 NZD per night

Guest favourite

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.

2–9 Jul

$155 NZD per night

Guest favourite

Bungalow in Pittsboro

4.9 out of 5 average rating, 109 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!

30 Nov – 7 Dec

$273 NZD per night

Guest favourite

Home in Pittsboro

4.99 out of 5 average rating, 276 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.

7–14 Aug

$207 NZD per night

Guest favourite

Home in Chapel Hill

4.95 out of 5 average rating, 175 reviews

Unique, bright and airy two bedroom

Remodeled space high up in the trees on a large wooded lot on a secluded street. Please note that access to this unit requires going up 3 flights of stairs. There are 2 queen beds, one in each of the 2 bedrooms. Private, but only about 7 miles directly outside Chapel Hill/Carrboro. Easy access to all Chapel Hill/Carrboro/UNC activities and Park and Ride for UNC sporting events.

16–23 Nov

$237 NZD per night

Holiday rentals for every style

Get the amount of space that is right for you

Popular amenities for Pittsboro holiday rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

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 holiday rentals in Pittsboro

Guest favourite

Home in Pittsboro

4.94 out of 5 average rating, 16 reviews

"Hawks Nest"

27 Jun – 4 Jul

$218 NZD per night

Guest favourite

Cabin in Pittsboro

4.96 out of 5 average rating, 23 reviews

Peaceful retreat in Fearrington Village

4–11 Oct

$249 NZD per night

Guest favourite

Bungalow in Pittsboro

4.92 out of 5 average rating, 48 reviews

Modern Cottage in the Pines, 15min to Chapel Hill

8–15 Sep

$310 NZD per night

Guest favourite

Home in Pittsboro

5.0 out of 5 average rating, 23 reviews

Relaxing Getaway Apartment

3–10 Mar

$239 NZD per night

Guest favourite

Tiny home in Pittsboro

5.0 out of 5 average rating, 24 reviews

Peacock Guest House at Red Pepper Farm

28 Jun – 5 Jul

$204 NZD per night

Guest favourite

Treehouse in Pittsboro

4.89 out of 5 average rating, 18 reviews

New H2O Oasis Tree House

27 Oct – 3 Nov

$351 NZD per night

Guest favourite

Tiny home in Chapel Hill

4.9 out of 5 average rating, 40 reviews

Cozy Tiny house near UNC

19–26 Nov

$175 NZD per night

Guest favourite

Loft in Chatham County

5.0 out of 5 average rating, 20 reviews

1 Bed 1 Bath Modern Loft Close to UNC/Duke

26 Oct – 2 Nov

$320 NZD per night

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Quick stats about holiday 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	$102 NZD before taxes and fees

Holiday houses in Pittsboro

Top-rated holiday rentals in Pittsboro

Shipping container in Pittsboro

Apartment in Pittsboro

Home in Pittsboro

Guesthouse in Saxapahaw

Home in Pittsboro

Tiny home in Chapel Hill

Guest suite in Mebane

Bungalow in Pittsboro

Guesthouse in Chapel Hill

Bungalow in Pittsboro

Home in Pittsboro

Home in Chapel Hill

Holiday rentals for every style

Hotels

Unique stays

Homes

Popular amenities for Pittsboro holiday rentals

Stay near Pittsboro's top sights

Other great holiday rentals in Pittsboro

Home in Pittsboro

Cabin in Pittsboro

Bungalow in Pittsboro

Home in Pittsboro

Tiny home in Pittsboro

Treehouse in Pittsboro

Tiny home in Chapel Hill

Loft in Chatham County

Quick stats about holiday rentals in Pittsboro

Total rentals

Rentals with dedicated workspaces

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Destinations to explore