Holiday Homes in Pittsboro

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Find holiday rentals that suit your style

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Check prices for these dates

Next weekend
20 Nov - 22 Nov
In two weeks
27 Nov - 29 Nov
In one month
11 Dec - 13 Dec
In two months
8 Jan - 10 Jan

Our top choices for Pittsboro holiday homes

A covered porch with a wooden bench, a doormat, and a view of a garden.

1. Downtown Pittsboro Glamtastic

Downtown Pittsboro Glamtastic
Pittsboro
9.2 out of 10, Wonderful, (10 reviews)
"Nice location. "
United States
Marcela V.
The price is AU$250
includes taxes & fees
29 Nov - 30 Nov
Downtown Pittsboro Glamtastic
A modern living room with a brown leather sofa, a ceiling fan, and a large window with curtains.

2. 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 AU$337
includes taxes & fees
10 Nov - 11 Nov
Charming Cozy Cottage Pittsboro
A small wooden structure with a blue door, a porch with a blue chair, and a wooden fence with flower decorations.

3. 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 AU$291
includes taxes & fees
18 Nov - 19 Nov
Curiously Cute B&B Private Woodshed- Pet friendly
A modern interior with a kitchen island, a hanging chair, and a large window.

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 AU$521
includes taxes & fees
10 Nov - 11 Nov
Romantic Treehouse: Retreat w/Fire Pit & Balcony
A modern kitchen with granite countertops, a large island, a built-in oven, and a black backsplash. There are large windows with a view of greenery outside.

5. 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 AU$518
includes taxes & fees
10 Nov - 11 Nov
Enchanting Galaxy Treehouse Getaway for Couples
A modern interior with a living area, kitchen, and a staircase leading to a balcony.

6. Secluded Oasis-Themed Treehouse Retreat

Secluded Oasis-Themed Treehouse Retreat
Pittsboro
9.8 out of 10, Exceptional, (8 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 AU$538
includes taxes & fees
15 Nov - 16 Nov
Secluded Oasis-Themed Treehouse Retreat
A modern living room with a loft bedroom, a wooden coffee table, and a large sliding glass door leading to an outdoor deck.

7. 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 AU$569
includes taxes & fees
17 Nov - 18 Nov
Secluded Beehive Treehouse Retreat w/Fire Pit
A modern living room with a brown leather sofa, a wooden coffee table, and a large sliding glass door leading to a deck.

8. Unique Treehouse Retreats in North Carolina

Unique Treehouse Retreats in North Carolina
Pittsboro
The price is AU$871
includes taxes & fees
15 Nov - 16 Nov
Unique Treehouse Retreats in North Carolina
A sunroom with a round table and chairs, large windows, and a ceiling fan.

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 AU$715
includes taxes & fees
15 Nov - 16 Nov
Tranquil Retreat w/ Piano, Firepit & Peloton
A modern interior with a kitchen, dining area, and a staircase leading to a balcony.

10. Two Unique Treehouses in Nature

Two Unique Treehouses in Nature
Pittsboro
The price is AU$888
includes taxes & fees
10 Nov - 11 Nov
Two Unique Treehouses in Nature
A modern living room with a loft, a sliding glass door to a deck, and a large window.

11. 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 AU$1,646
includes taxes & fees
18 Nov - 19 Nov
Unique Treehouse Retreats in NC Nature
A cozy room with a bed, a sofa, a bench, and a coffee table. There are large windows with a view of trees.

12. 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 AU$412
includes taxes & fees
10 Nov - 11 Nov
Tiny Tarheel: Cozy Retreat Near UNC-Tiny House
A house with a gravel patio, three Adirondack chairs, and a fire pit.

13. 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 AU$328
includes taxes & fees
15 Nov - 16 Nov
The Cozy Bungalow - Official Historic Home Near UNC!
A single-story house with a porch, a front door, and a mailbox.

14. 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 AU$380
includes taxes & fees
10 Nov - 11 Nov
Jordan Lake Bungalow with boat parking
Private kitchen

15. 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 AU$314
includes taxes & fees
15 Nov - 16 Nov
Grandma’s House - Minutes from UNC, Firepit, Ninja Creami Available to Rent
A modern kitchen with white cabinetry, stainless steel appliances, and a granite countertop.

16. 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 AU$369
includes taxes & fees
18 Nov - 19 Nov
Jo Mac Cottage- Quiet Home near UNC Chapel Hill
A compact, open-plan living space with a kitchenette, a dining area, and a seating area with a sofa and chairs.

17. Tiny House - Farm Charm

Tiny House - Farm Charm
Siler City
10.0 out of 10, Exceptional, (7 reviews)
"Amazing place to stay. The things offered such as the farm animals, fishing, etc a bang for your bucks. "
United States
Amanda B.
The price is AU$295
includes taxes & fees
1 Dec - 2 Dec
Tiny House - Farm Charm
A modern kitchen with white cabinetry, stainless steel appliances, a dining area with a wooden table and bench, and a view of greenery outside.

18. Historic Northside House w/Art, Walk to Downtown!

Historic Northside House w/Art, Walk to Downtown!
Chapel Hill
9.8 out of 10, Exceptional, (16 reviews)
"Great location for visiting Chapel Hill"
United States
Dan S.
The price is AU$897
includes taxes & fees
16 Nov - 17 Nov
Historic Northside House w/Art, Walk to Downtown!
A backyard patio with outdoor furniture, a fire pit, and string lights.

19. 3 Bedroom Homestead Getaway - Walkable Carrboro, Minutes to UNC

3 Bedroom Homestead Getaway - Walkable Carrboro, Minutes to UNC
Carrboro
10.0 out of 10, Exceptional, (11 reviews)
"Property was very clean and appealing. Close to everything we needed.very well stocked. Great place looking forward to future visits"
United States
bernie v.
The price is AU$695
includes taxes & fees
23 Nov - 24 Nov
3 Bedroom Homestead Getaway - Walkable Carrboro, Minutes to UNC
A dining area with a round wooden table, blue upholstered chairs, a wicker hanging light fixture, and a rattan chair.

20. Stylish Downtown Bungalow with Fire Pit

Stylish Downtown Bungalow with Fire Pit
Carrboro
10.0 out of 10, Exceptional, (11 reviews)
"We loved this place... spacious, super clean, fenced yard, two full baths with a good laundry setup, kitchen has everything you need (and not a bunch of stuff you don't)... great location near downtown Carrboro. The host was super responsive. A-plus!"
United States
scott s.
The price is AU$764
includes taxes & fees
16 Nov - 17 Nov
Stylish Downtown Bungalow with Fire Pit
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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Learn more about Pittsboro

This small town charms visitors with its historic courthouse circle and quirky shops selling local pottery and folk art. Spend afternoons exploring nearby Jordan Lake's hiking trails or sampling craft spirits at the family-owned distillery that welcomes curious tasters.

See all hotels in Pittsboro
A historic courthouse with a clock tower, brick facade, and American flag.

Top reviews in Pittsboro

An outdoor dining area with tables set for four, surrounded by a brick pathway and lush greenery.
Rizzo Center, a Destination by Hyatt Hotel

Rizzo Center, a Destination by Hyatt Hotel

Rizzo Center, a Destination by Hyatt Hotel
Chapel Hill

10/10 Excellent

Fabulous place to stay. Well priced and well set up for executive business stays.
Australia
Martin
Reviewed September 16, 2024
Rizzo Center, a Destination by Hyatt Hotel