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Pittsboro Holiday Rentals

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Our top choices for Pittsboro holiday rentals

1. Downtown Pittsboro Boho Loft

Downtown Pittsboro Boho Loft
Pittsboro
9.6 out of 10, Exceptional, (8 reviews)
"Great location. Walk to all the restaurants and bars!"
United States
Jeff S.
The price is NZ$302
includes taxes & fees
3 Nov - 4 Nov
Downtown Pittsboro Boho Loft

2. Downtown Pittsboro Glamtastic

Downtown Pittsboro Glamtastic
Pittsboro
9.2 out of 10, Wonderful, (10 reviews)
"Nice location. "
United States
Marcela V.
The price is NZ$300
includes taxes & fees
30 Nov - 1 Dec
Downtown Pittsboro Glamtastic

3. Curiously Cute B&B Private Woodshed- Pet friendly

Curiously Cute B&B Private Woodshed- Pet friendly
Pittsboro
9.6 out of 10, Exceptional, (30 reviews)
"Thank you so much for the wonderful and cute place to stay! The location was perfect for walking to downtown and every person we met was so welcoming. Breakfast was delicious too! "
United States
Krystal B.
The price is NZ$355
includes taxes & fees
10 Nov - 11 Nov
Curiously Cute B&B Private Woodshed- Pet friendly

4. Romantic Treehouse: Retreat w/Fire Pit & Balcony

Romantic Treehouse: Retreat w/Fire Pit & Balcony
Pittsboro
9.8 out of 10, Exceptional, (6 reviews)
"The host was great, I booked for the wrong day but she accommodated us. The place was so lovely. "
United States
Nicole H.
The price is NZ$691
includes taxes & fees
15 Nov - 16 Nov
Romantic Treehouse: Retreat w/Fire Pit & Balcony

5. Charming Cozy Cottage Pittsboro

Charming Cozy Cottage Pittsboro
Pittsboro
9.4 out of 10, Exceptional, (3 reviews)
"Cozy place!"
United States
Sarah U.
The price is NZ$400
includes taxes & fees
3 Nov - 4 Nov
Charming Cozy Cottage Pittsboro

6. Secluded Oasis-Themed Treehouse Retreat

Secluded Oasis-Themed Treehouse Retreat
Pittsboro
9.8 out of 10, Exceptional, (7 reviews)
"Such a fun place to stay! Every detail of the home tied into the theme, and the atmosphere of the property made it feel like a peaceful wooded retreat."
United States
Heidi B.
The price is NZ$629
includes taxes & fees
3 Nov - 4 Nov
Secluded Oasis-Themed Treehouse Retreat

7. Enchanting Galaxy Treehouse Getaway for Couples

Enchanting Galaxy Treehouse Getaway for Couples
Pittsboro
9.8 out of 10, Exceptional, (13 reviews)
"Clean and family friendly! We had a great time at the Galaxy treehouse!"
United States
Maureen W.
The price is NZ$629
includes taxes & fees
3 Nov - 4 Nov
Enchanting Galaxy Treehouse Getaway for Couples

8. Secluded Beehive Treehouse Retreat w/Fire Pit

Secluded Beehive Treehouse Retreat w/Fire Pit
Pittsboro
9.2 out of 10, Wonderful, (9 reviews)
"Great retreat and so close to Chapel Hill and many amenities, yet feels remote."
United States
Jason W.
The price is NZ$624
includes taxes & fees
3 Nov - 4 Nov
Secluded Beehive Treehouse Retreat w/Fire Pit

9. Unique Treehouse Retreats in North Carolina

Unique Treehouse Retreats in North Carolina
Pittsboro
The price is NZ$1,034
includes taxes & fees
3 Nov - 4 Nov
Unique Treehouse Retreats in North Carolina

10. Quiet Retreat - Piano, Firepit, Peloton

Quiet Retreat - Piano, Firepit, Peloton
3.0 star property
Pittsboro
The price is NZ$1,046
includes taxes & fees
5 Nov - 6 Nov
Quiet Retreat - Piano, Firepit, Peloton

11. Tranquil Retreat w/ Piano, Firepit & Peloton

Tranquil Retreat w/ Piano, Firepit & Peloton
Pittsboro
9.8 out of 10, Exceptional, (16 reviews)
"Great host! Perfect Stay!"
United States
James H.
The price is NZ$875
includes taxes & fees
3 Nov - 4 Nov
Tranquil Retreat w/ Piano, Firepit & Peloton

12. Two Unique Treehouses in Nature

Two Unique Treehouses in Nature
Pittsboro
The price is NZ$1,046
includes taxes & fees
3 Nov - 4 Nov
Two Unique Treehouses in Nature

13. Unique Treehouse Retreats in NC Nature

Unique Treehouse Retreats in NC Nature
Pittsboro
10.0 out of 10, Exceptional, (2 reviews)
"Really great accommodations. We hope to come back."
United States
sarah B.
Unique Treehouse Retreats in NC Nature

14. Two Tree Houses - Beehive & H20

Two Tree Houses - Beehive & H20
3.0 star property
Pittsboro
The price is NZ$1,107
includes taxes & fees
8 Nov - 9 Nov
Two Tree Houses - Beehive & H20

15. The Cozy Bungalow - Official Historic Home Near UNC!

The Cozy Bungalow - Official Historic Home Near UNC!
Chapel Hill
9.6 out of 10, Exceptional, (36 reviews)
"Had a wonderful stay. The host was fantastic. Location worked great for football game weekend. Highly recommend."
United States
Kenny
The price is NZ$392
includes taxes & fees
9 Nov - 10 Nov
The Cozy Bungalow - Official Historic Home Near UNC!

16. Tiny Tarheel: Cozy Retreat Near UNC-Tiny House

Tiny Tarheel: Cozy Retreat Near UNC-Tiny House
Chapel Hill
9.8 out of 10, Exceptional, (24 reviews)
"Excellent little place to stay. Great location. "
United States
Lonny P.
The price is NZ$499
includes taxes & fees
3 Nov - 4 Nov
Tiny Tarheel: Cozy Retreat Near UNC-Tiny House

17. Jordan Lake Bungalow with boat parking

Jordan Lake Bungalow with boat parking
New Hill
10.0 out of 10, Exceptional, (51 reviews)
"Amazing stay! "
United States
Shelby L.
The price is NZ$475
includes taxes & fees
15 Nov - 16 Nov
Jordan Lake Bungalow with boat parking

18. Guest Suite near UNC!

Guest Suite near UNC!
Chapel Hill
9.6 out of 10, Exceptional, (84 reviews)
"Would definitely stay there again!"
United States
Scott P.
The price is NZ$304
includes taxes & fees
3 Nov - 4 Nov
Guest Suite near UNC!

19. Lovely Farm Cabin Experience

Lovely Farm Cabin Experience
Siler City
10.0 out of 10, Exceptional, (8 reviews)
"Cabin was amazing! So clean and cozy. We reslly enjoyed the hot tub and animals on the farm."
United States
Britt
The price is NZ$395
includes taxes & fees
3 Nov - 4 Nov
Lovely Farm Cabin Experience

20. Jo Mac Cottage- Quiet Home near UNC Chapel Hill

Jo Mac Cottage- Quiet Home near UNC Chapel Hill
Chapel Hill
9.0 out of 10, Wonderful, (15 reviews)
"Great beds."
United States
Joan H.
The price is NZ$440
includes taxes & fees
3 Nov - 4 Nov
Jo Mac Cottage- Quiet Home near UNC Chapel Hill
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Pittsboro Hotel Reviews

Find out more about Pittsboro

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Pittsboro holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Pittsboro. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Pittsboro. Seeing all the best attractions is bound to make you fall in love with Pittsboro. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Pittsboro short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find a holiday rental in Pittsboro?

Yes, there are holiday rentals in Pittsboro close to McIntyre's Fine Books and Bookends, or you can select a more secluded option if you're looking for a relaxing stay. Pittsboro is known for its art.

What are some of the best holiday rentals that Pittsboro has to offer?

Spacious Cary Home w/ Gym, Game Room, Huge Fenced Yard!: This holiday home rental outside of Pittsboro is located in the city centre, and has a fireplace, a patio and air conditioning to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and an arcade/games room.

How many holiday rentals are there in Pittsboro?

With 25 Expedia holiday rentals, you're guaranteed to find just the right place for your Pittsboro stay.

What’s there to see and do in Pittsboro?

Enjoy the outdoors at Pittsboro Town Park and Seaforth Beach, or simply take in cultural attractions like Chatham Historical Museum and The Joyful Jewel. Small Museum of Folk Art and Starrlight Mead are other places to visit while you're in town.

What’s a holiday rental in Pittsboro like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Pittsboro. Holiday rentals feature extras such as hot tubs, fire pits and patios so you'll have all the comforts of home. If you're concerned about a clean environment, a holiday rental can offer a sense of security away from public hotel lifts and busy concierge desks while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular option for family gatherings.