Pittsboro Vacation Rentals

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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Pittsboro vacation rentals

A forested area with a seating arrangement of blue chairs, large rocks, and a small waterfall.

1. 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 SAR 688
SAR 1,448 total
includes taxes & fees
15 Nov - 16 Nov
Romantic Treehouse: Retreat w/Fire Pit & Balcony
A kitchen with wooden floors, a brick wall, and a window with a view.

2. Downtown Pittsboro Boho Loft

Downtown Pittsboro Boho Loft
Pittsboro
9.0 out of 10, Wonderful, (9 reviews)
"This was such a lovely place to stay in historic Pittsboro. The restaurants and shops are lovely within walking distance. Great night, thank you!"
United States
Heather
The price is SAR 439
SAR 722 total
includes taxes & fees
30 Nov - 1 Dec
Downtown Pittsboro Boho Loft
A wooden deck with a table and chairs, surrounded by a metal fence and trees.

3. Secluded Oasis-Themed Treehouse Retreat

Secluded Oasis-Themed Treehouse Retreat
Pittsboro
9.8 out of 10, Exceptional, (8 reviews)
"Really lovely treehouse! It is in a horseshoe with three other similar properties, all with different themes. The Oasis H20 obviously had a water theme that was shown in the decor and a cute water feature outside. The bathroom was huge! Main bedroom a little on the small size but perfectly comfortable. Loft bed really only for kids! Nice location and the property was clean. We enjoyed sitting out by the firepit."
United States
Georgina
The price is SAR 680
SAR 1,439 total
includes taxes & fees
15 Nov - 16 Nov
Secluded Oasis-Themed Treehouse Retreat
A wooden deck with a glass railing overlooking a forested area.

4. Two Tree Houses - Beehive & H20

Two Tree Houses - Beehive & H20
3.0 star property
Pittsboro
The price is SAR 1,081
SAR 2,339 total
includes taxes & fees
15 Nov - 16 Nov
Two Tree Houses - Beehive & H20
A cabin with a small waterfall, surrounded by rocks and trees.

5. Unique Treehouse Retreats in North Carolina

Unique Treehouse Retreats in North Carolina
Pittsboro
The price is SAR 770
SAR 2,181 total
includes taxes & fees
15 Nov - 16 Nov
Unique Treehouse Retreats in North Carolina
An outdoor patio area with a pergola covered in string lights, surrounded by chairs and tables.

6. 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 SAR 439
SAR 855 total
includes taxes & fees
13 Nov - 14 Nov
Charming Cozy Cottage Pittsboro
A wooden staircase leading up to a wooden deck with a bench, surrounded by a forested area with rocks and gravel paths.

7. Enchanting Galaxy Treehouse Getaway for Couples

Enchanting Galaxy Treehouse Getaway for Couples
Pittsboro
9.8 out of 10, Exceptional, (14 reviews)
"Very clean and loved the decor!"
United States
Michael
The price is SAR 680
SAR 1,447 total
includes taxes & fees
18 Nov - 19 Nov
Enchanting Galaxy Treehouse Getaway for Couples
A cabin with a small waterfall, surrounded by rocks and trees.

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 SAR 668
SAR 1,426 total
includes taxes & fees
15 Nov - 16 Nov
Secluded Beehive Treehouse Retreat w/Fire Pit
A covered porch with white rocking chairs, a blue table, and a green door.

9. 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 SAR 788
SAR 1,921 total
includes taxes & fees
15 Nov - 16 Nov
Tranquil Retreat w/ Piano, Firepit & Peloton
A covered porch with a wooden bench, a doormat, and a view of a garden.

10. Downtown Pittsboro Glamtastic

Downtown Pittsboro Glamtastic
Pittsboro
9.2 out of 10, Wonderful, (10 reviews)
"Nice location. "
United States
Marcela V.
The price is SAR 360
SAR 639 total
includes taxes & fees
29 Nov - 30 Nov
Downtown Pittsboro Glamtastic
A bedroom with a wooden headboard, a quilted bedspread, two bedside lamps, and a window on one side.

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

Curiously Cute B&B Private Woodshed- Pet friendly
Pittsboro
9.6 out of 10, Exceptional, (31 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 SAR 368
SAR 772 total
includes taxes & fees
19 Nov - 20 Nov
Curiously Cute B&B Private Woodshed- Pet friendly
A wooden deck with a staircase leading to a blue building, surrounded by trees and outdoor seating.

12. Two Unique Treehouses in Nature

Two Unique Treehouses in Nature
Pittsboro
The price is SAR 1,130
SAR 2,374 total
includes taxes & fees
18 Nov - 19 Nov
Two Unique Treehouses in Nature
A wooden deck with a glass railing, wooden chairs, and a mosaic wall.

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.
The price is SAR 2,262
SAR 4,439 total
includes taxes & fees
8 Dec - 9 Dec
Unique Treehouse Retreats in NC Nature
A covered porch with white rocking chairs, a blue table, and a green door.

14. Quiet Retreat - Piano, Firepit, Peloton

Quiet Retreat - Piano, Firepit, Peloton
3.0 star property
Pittsboro
The price is SAR 728
SAR 2,210 total
includes taxes & fees
17 Nov - 18 Nov
Quiet Retreat - Piano, Firepit, Peloton
A wooden cabin with a hammock, two chairs, and a door with a window.

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

Tiny Tarheel: Cozy Retreat Near UNC-Tiny House
Chapel Hill
9.8 out of 10, Exceptional, (25 reviews)
"Excellent little place to stay. Great location. "
United States
Lonny P.
The price is SAR 338
SAR 1,066 total
includes taxes & fees
16 Nov - 17 Nov
Tiny Tarheel: Cozy Retreat Near UNC-Tiny House
A single-story house with a porch, a front door, and a mailbox.

16. Jordan Lake Bungalow with boat parking

Jordan Lake Bungalow with boat parking
New Hill
10.0 out of 10, Exceptional, (51 reviews)
"Very relaxing place to stay and host was excellent with responses. Would definitely stay again if in the area."
United States
Angela C.
The price is SAR 375
SAR 983 total
includes taxes & fees
17 Nov - 18 Nov
Jordan Lake Bungalow with boat parking
A house with a gravel patio, three Adirondack chairs, and a fire pit.

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

The Cozy Bungalow - Official Historic Home Near UNC!
Chapel Hill
9.4 out of 10, Exceptional, (37 reviews)
"Had a wonderful stay. The host was fantastic. Location worked great for football game weekend. Highly recommend."
United States
Kenny
The price is SAR 422
SAR 836 total
includes taxes & fees
15 Nov - 16 Nov
The Cozy Bungalow - Official Historic Home Near UNC!
A hallway with a wooden floor, a gray door, and white-framed windows.

18. 3 Bedroom House at Pine Forest Hideaway Near UNC

3 Bedroom House at Pine Forest Hideaway Near UNC
Chapel Hill
9.8 out of 10, Exceptional, (14 reviews)
"Location excellent, Pet friendly, provided everything needed for stay."
United States
JOSHUA E.
The price is SAR 1,028
SAR 1,225 total
includes taxes & fees
16 Nov - 17 Nov
3 Bedroom House at Pine Forest Hideaway Near UNC
A barn with hay bales stored on pallets, a sandy floor, and a metal roof structure.

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 SAR 559
SAR 822 total
includes taxes & fees
17 Nov - 18 Nov
Lovely Farm Cabin Experience
A wooden deck with a round table and four chairs, surrounded by a railing and a patterned rug.

20. Grandma’s House - Minutes from UNC, Firepit, Ninja Creami Available to Rent

Grandma’s House - Minutes from UNC, Firepit, Ninja Creami Available to Rent
Chapel Hill
9.8 out of 10, Exceptional, (34 reviews)
"Calm and peaceful but close to campus!"
United States
Jessica W.
The price is SAR 388
SAR 803 total
includes taxes & fees
22 Nov - 23 Nov
Grandma’s House - Minutes from UNC, Firepit, Ninja Creami Available to Rent
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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Find vacation rentals that suit your style

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Top Pittsboro Hotel Reviews

A modern hotel with a distinctive curved sculpture in front, a well-lit building, and a landscaped area.
Hampton Inn & Suites Pittsboro

Hampton Inn & Suites Pittsboro

Hampton Inn & Suites Pittsboro
Pittsboro

10/10 Excellent

Beautiful property in a quiet setting within walking distance of multiple restaurants.
United States
Ricky
Reviewed November 7, 2026
Hampton Inn & Suites Pittsboro

Frequently Asked Questions

Can I find a vacation rental in Pittsboro?

Yes, you can find vacation rentals in Pittsboro close to McIntyre's Fine Books and Bookends, or you can choose a more remote option if you want a relaxing stay. Pittsboro is known for its art.

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

Spacious Cary Home w/ Gym, Game Room, Huge Fenced Yard!: This vacation home rental near Pittsboro is located in the city center 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 you can cook with friends or family. You can relax into your vacation with a garden and an arcade game room.

How many vacation rentals are there in Pittsboro?

With 25 Expedia vacation rentals, you're sure 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 vacation rental in Pittsboro like?

A vacation rental is a private property you can stay in for a couple of days or more in Pittsboro. Vacation rentals offer extras like WiFi and washers and dryers so you'll have everything you want. If you're concerned about a sanitized environment, vacation rentals can offer a sense of seclusion away from public hotel elevators and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a hotel, which is another reason why a vacation rental is an attractive choice for family trips or small group gatherings.