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Pittsboro Vacation Rentals

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Check prices for these dates

In two weeks
Jan 9 - Jan 11
In two months
Feb 20 - Feb 22
In three months
Mar 20 - Mar 22
In four months
Apr 17 - Apr 19

Our top choices for Pittsboro vacation rentals

TV
Cozy Downtown Pittsboro Home

Vacation Home in Pittsboro

Cozy Downtown Pittsboro Home
2.0 star property
10.0 out of 10, Exceptional, (5)
"Had a great time in Pittsboro, the place was cozy and exactly what we needed"
United States
peter n.
The price is ￥11,228
￥24,015 total
includes taxes & fees
Jan 12 - Jan 13, 2026
Cozy Downtown Pittsboro Home
Property grounds
Natural Splendor; Ultimate Off Grid Experience!

Cabin in Pittsboro

Natural Splendor; Ultimate Off Grid Experience!
10.0 out of 10, Exceptional, (6)
"Great host, if you want to know what off grid living is all about, this is the perfect place to stay."
United States
Sandy
The price is ￥13,912
￥35,912 total
includes taxes & fees
Dec 27 - Dec 28
Natural Splendor; Ultimate Off Grid Experience!
Exterior
Log Cabin with loft

Cabin in Pittsboro

Log Cabin with loft
9.8 out of 10, Exceptional, (87)
"The cabin was charming and exactly what we were looking for! Would definitely stay again!"
United States
Rhea
The price is ￥19,518
￥27,481 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Log Cabin with loft
TV
Downtown Pittsboro Boho Loft

Apartment in Pittsboro

Downtown Pittsboro Boho Loft
10.0 out of 10, Exceptional, (4)
"Great location. Walk to all the restaurants and bars!"
United States
Jeff S.
The price is ￥14,989
￥26,231 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Downtown Pittsboro Boho Loft
Outdoor dining
H2O Oasis Tree House

Cabin in Pittsboro

H2O Oasis Tree House
9.6 out of 10, Exceptional, (4)
"This is the fourth time we’ve stayed in the tree house village - all have been excellent. Quiet and peaceful. It’s a great location for us as we visit family in Briar Chapel development. Place is clean and well appointed - will definitely be back "
United States
John D.
The price is ￥25,919
￥54,102 total
includes taxes & fees
Jan 6 - Jan 7, 2026
H2O Oasis Tree House
Fridge, microwave, oven, stovetop
Downtown Pittsboro Glamtastic

Vacation Home in Pittsboro

Downtown Pittsboro Glamtastic
9.2 out of 10, Wonderful, (5)
"Good place to relax "
United States
Casey Y.
The price is ￥14,989
￥27,792 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Downtown Pittsboro Glamtastic
Terrace/patio
Galaxy Tree House Sum

Cabin in Pittsboro

Galaxy Tree House Sum
9.6 out of 10, Exceptional, (7)
"Our family of 4 had an amazing time at the Galaxy Treehouse. We appreciate all of the attention to details and how immaculate this property was. The outdoor areas added to the overall experience. This was an unforgettable trip. Highly recommend!!"
United States
Christy P.
The price is ￥25,919
￥57,022 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Galaxy Tree House Sum
Terrace/patio
Cozy Beehive Treehouse

Cabin in Pittsboro

Cozy Beehive Treehouse
9.0 out of 10, Wonderful, (7)
"Perfect location to visit family! We were only 5 minutes away. Everything we needed to have some private time. Kitchen area was perfect for our breakfast needs! Will come again. "
United States
Anna P.
The price is ￥24,046
￥54,790 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Cozy Beehive Treehouse
Outdoor dining
Full Bloom Tree House

Cabin in Pittsboro

Full Bloom Tree House
9.4 out of 10, Exceptional, (3)
"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 ￥25,919
￥54,618 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Full Bloom Tree House
Fridge, microwave, oven, stovetop
Quiet Retreat - Piano, Firepit, Peloton - 30 min to RTP

Vacation Home in Pittsboro

Quiet Retreat - Piano, Firepit, Peloton - 30 min to RTP
9.2 out of 10, Wonderful, (5)
"Great place to stay "
United States
Casey Y.
The price is ￥28,417
￥69,905 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Quiet Retreat - Piano, Firepit, Peloton - 30 min to RTP
Outdoor dining
Charming Cozy Cottage Pittsboro

Vacation Home in Pittsboro

Charming Cozy Cottage Pittsboro
The price is ￥18,268
￥36,411 total
includes taxes & fees
Dec 27 - Dec 28
Charming Cozy Cottage Pittsboro
Fridge, microwave, oven, stovetop
Two Tree Houses - Beehive & H20

Apartment in Pittsboro

Two Tree Houses - Beehive & H20
The price is ￥32,789
￥89,140 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Two Tree Houses - Beehive & H20
Outdoor dining
Two Tree Houses - Galaxy & Full Bloom

Cabin in Pittsboro

Two Tree Houses - Galaxy & Full Bloom
The price is ￥40,596
￥89,140 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Two Tree Houses - Galaxy & Full Bloom
Outdoor dining
Elevate Treehouses - Book all 4 treehouses!

Cabin in Pittsboro

Elevate Treehouses - Book all 4 treehouses!
The price is ￥73,386
￥156,812 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Elevate Treehouses - Book all 4 treehouses!
Exterior detail
The Acorn Suites

Aparthotel in Mebane

The Acorn Suites
2.5 star property
9.6 out of 10, Exceptional, (57)
"A wonderful place to stay, clean, hospitable and comfortable. "
United States
Donald
The price is ￥24,372
￥27,478 total
includes taxes & fees
Jan 1 - Jan 2, 2026
The Acorn Suites
Fridge, microwave, oven, stovetop
New & Clean 2 Bed Walltown Home. Walk to Duke! A

Apartment in Durham

New & Clean 2 Bed Walltown Home. Walk to Duke! A
10.0 out of 10, Exceptional, (13)
"The host was amazing and very responsive.The place was very nice and clean. The location of Duke was perfect. Would definitely stay here again."
United States
Cindy J.
The price is ￥12,713
￥33,216 total
includes taxes & fees
Jan 11 - Jan 12, 2026
New & Clean 2 Bed Walltown Home. Walk to Duke! A
Fridge, microwave, oven, stovetop
Grandma’s House - Minutes from UNC

Vacation Home in Chapel Hill

Grandma’s House - Minutes from UNC
2.0 star property
9.8 out of 10, Exceptional, (16)
"We had a great stay at Grandma's House. It was the perfect place for us and our dogs to spend the weekend! "
United States
Brad K.
The price is ￥14,053
￥27,606 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Grandma’s House - Minutes from UNC
TV, offices
100 Year-Old Historic Brick 2BR Loft High Ceiling5

Apartment in Downtown Durham

100 Year-Old Historic Brick 2BR Loft High Ceiling5
9.6 out of 10, Exceptional, (5)
"Very cool property!"
United States
Jessica L.
The price is ￥12,960
￥35,091 total
includes taxes & fees
Jan 20 - Jan 21, 2026
100 Year-Old Historic Brick 2BR Loft High Ceiling5
Interior
Hemingway’s Hideaway | 2BR w/ King + Pvt Patio

Vacation Home in Fuquay-Varina

Hemingway’s Hideaway | 2BR w/ King + Pvt Patio
10.0 out of 10, Exceptional, (11)
"Really enjoyed our stay, nice, quiet, Owners were very responsive and helpful."
United States
Brian P.
The price is ￥12,195
￥45,818 total
includes taxes & fees
Jan 13 - Jan 14, 2026
Hemingway’s Hideaway | 2BR w/ King + Pvt Patio
Apartment | 1 bedroom
Lakewood Lyon Park Renovated Cottage Near Duke 26B

Apartment in Durham

Lakewood Lyon Park Renovated Cottage Near Duke 26B
2.0 star property
10.0 out of 10, Exceptional, (1)
"I felt very comfortable at this cottage. My wife and I enjoyed the kitchen and walk in closet. Laundry on site! There were dishes and pots and pans. A microwave and full size oven and refrigerator. It was very clean and it suited our needs perfectly!"
United States
Kevin
The price is ￥10,418
￥24,267 total
includes taxes & fees
Dec 29 - Dec 30
Lakewood Lyon Park Renovated Cottage Near Duke 26B
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

Sonesta Select Raleigh Durham Airport Morrisville

Sonesta Select Raleigh Durham Airport Morrisville

10/10 Excellent
"The staff was friendly and helpful. "
Martha 1-night trip
Posted 15 hours ago
Sonesta Select Raleigh Durham Airport Morrisville

Find out more about Pittsboro

Search for holiday rentals in Pittsboro on Expedia! You can easily find your home rentals, villas, holiday apartments in Pittsboro using one of the methods below:

  • View our selection of featured holiday rentals in Pittsboro
  • Use the map to find apartments and other holiday homes in the Pittsboro neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Pittsboro while they last

Look no further and take a look at our great range of rental properties in 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?

Golf Destination w/ Private Driving Range w/ Lights, and Bar.: This vacation home rental near Pittsboro offers a fireplace, a barbecue grill, and air-conditioning to help you feel perfectly comfortable in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

How many vacation rentals are there in Pittsboro?

With 18 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 Seaforth Beach and Nooe Memorial Park, 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.