
Holiday rentals with outdoor seating in Pittsboro
Find and book unique rentals with outdoor seating on Airbnb
Top-rated rentals with outdoor seating in Pittsboro
Guests agree: these rentals with outdoor seating are highly rated for location, cleanliness and more.

Cozy Art Cabin among organic gardens near UNC/Duke
This is a shabby-chic art-studio cabin. It has a stunning walk-in shower w/ an under-water mural mosaic. There are mosaic doors & windows throughout the space. This space shares a common wall with my mosaic art studio. There are 2- sweet Aussie shepherds and 2- domestic cats on the property. Guests are welcome to eat meals on the back deck or beautiful gardens. There is a private shower, sink & composting toilet in cabin. New kitchenette recently added. Would like a long-term day-shift renter.

Art, Beauty, Nature: A Woodland Retreat
Relax in our bright and artistic guest suite — all hand-built with unique touches throughout. -Private entrance & terrace -Comfortable king-sized bed -Smart TV -Kitchenette with small refrigerator, microwave, toaster oven -Private patio w/ patio lights & seating for 2 -Unique art -Complimentary coffee & tea Great for getaways, rest, retreats, time in nature! 15 mins from restaurants, cafes and the charming towns of Carrboro, Pittsboro, and Saxapahaw. 10-15 mins to Chapel Hill, 20 to UNC.

Quirky Fun B&B: Tree House Unit
Refurbished container building by an architect professor at UNC-C for a traveling art exhibit A space efficient room (8’x8’) w/ a tall, airy ceiling, full size bed, private bath, Mini fridge (holds 10x 12oz cans), coffee station w Keurig etc, smart TV for streaming & deck overlooking gardens w/ outsider folk art scattered about property. Pass for FREE tasting @ Fair Game Distillery Included! Rates SINGLE OCCUPANCY add’l $20/person/night applies. Hammock, picnic tables, playground & firepit

White Oak Hill, minutes to UNC & Duke
Have everything you need for a hassle-free Chapel Hill/Carrboro retreat at this perfectly appointed home just 6 miles west of the city. Newly remodeled to please with luxury finishes inside and out, this vacation rental is highlighted by serene and beautiful country views from every window. This spacious layout sleeps 10 with 4 bedrooms, 2 full bathrooms, 1 half bath, 2 living rooms, bar seating and separate dining room. Foodies will love cooking in the fully equipped gourmet kitchen!

Christmas Tree Farm Bunkhouse near Jordan Lake
Ever thought it would be fun to experience a day at a real working Christmas Tree Farm? Be our guest at the bunkhouse, a beautiful 320 sq ft tiny house full of character. Remodeled from salvaged materials on the farm, this bunkhouse features a full kitchen, bathroom with roomy bedroom and living room. Relax on the porch or roast marshmallows by the firepit. You can take a stroll through the Christmas trees, by the pond and in the spring and summer, through our U-pick flower patch.

Anna Belle's Retreat - Belle (Side B)
This renovated duplex offers tranquility, style and comfort. Situated in the North Chatham area, we are just a short drive to Chapel Hill and Pittsboro. Jordan Lake and Haw River are also close by. Nestled in the pines yet within walking distance to nearby shopping, you'll experience the peacefulness of being in the country with the conveniences of being in the city. Enjoy the private screened porch with adjoining patio and grilling area. Need more space? Unit A is also available.

Luxurious Modernist Tree House
Stunning, private, and truly one-of-a-kind—this unique home is perfect for a vacation, staycation, special occasion, or simply celebrating everyday life. Designed by renowned modernist architect Frank Harmon. The 2,128-square-foot residence sits on 1.3 acres and was crafted with meticulous attention to detail. Inside, you’ll feel nestled among the treetops while remaining conveniently close to restaurants, shopping, downtown Raleigh, WakeMed, UNC, Duke, and Research Triangle Park.

Carriage House-32 Acre Wooded Lot & Trails & Pond
-private 2015 carriage house in Chapel Hill; less than 2 miles from I-40 -less than 8 miles from UNC; less than 20 minutes from Duke -2 bedrooms with queen, 2 twins & a trundle bed -32 acre private wooded lot with 2 mi. of trails w/ stocked pond -open floor plan - 1000 sq.ft. -fully stocked kitchen w/ fresh eggs -high speed wireless internet -on-site washer and dryer (free) -stairs from ground to apartment -4 vehicles parking spaces -outdoor grill & 2 fire pits w/ Adirondack chairs

Secluded Treehouse - 27 acres on Terrells Creek
Private “Treehouse” Home on 27 acres in the woods. Enjoy Walking trails, creek, fire pit, outdoor games, hammocks, swings . 20 mins to downtown Pittsboro, Carrboro, Chapel Hill, Jordan Lake -40 mins to Raleigh, Cary and Durham but worlds away from it all. Come relax and remember what it’s like to be away from noise and light pollution and hear only crickets at night. 1 King bedroom + private loft with king and queen beds. (loft accessed by stair ladder).

Cozy Tiny house near UNC
Explore this cozy 400 square feet retreat around a 15 minute drive from UNC. The tiny house behind the main house in the gated yard. Enjoy the open floor plan with a full bathroom with a walk-in shower, kitchenette, and a charming patio. It is the perfect for sports fans and travelers seeking a Chapel Hill getaway with all the comforts of home! Hosts are close by to help with request during your stay. Pets are welcomed!

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!

Guest House @ Mission Farm, quiet, farm setting
18 minutes to down town Chapel Hill/Franklin Street or historic & quaint downtown Pittsboro. Relax in a beautiful farm house on 10 acres near the Haw River with rolling pastures, woods, chickens, ducks, cows and and pond views. GREAT couple weekend getaway, those traveling to UNC/Duke sporting events, families with kids. Can interact with animals and relax in serene setting
Popular amenities for outdoor seating rentals in Pittsboro
House rentals with outdoor seating

Cozy Casita minutes to Downtown And Jordan Lake!

Family Getaway | Fire Pit + Treehouse on 2.5 acres

Modern Spacious Tiny Home Nestled in the Trees

Hot Tub + Walk to Downtown | Fire Pit | Game Table

Highland Comfort - Private Peaceful Retreat

Modern 3-Bdrm One-Level w/Fenced Backyard - Apex!

Private retreat, walk/bike to town.

Calumet's Getaway - Blocks from Downtown Apex
Apartment rentals with outdoor seating

Walk to UNC and Franklin Street

Fresh Mill House Apt in Walkable Downtown Carrboro

Pinehurst #6 Garden Getaway

2 blocks from UNC - Gorgeous w/Tesla Charger!

Pvt Apartment Centrally Located

2-BR apt/garden near downtown Durham arts & eats

Walk to Downtown & Duke- King bed

LuLu's Oasis
Apartment rentals with outdoor seating

Chapel Hill Family Haven

Cary Urban Oasis

Second floor 1 BR condominium near The Village

McCauley House A | Classic, Updated & Functional

Lake view condo w/office, walk to food/greenway

Fully stocked, clean, quiet, comfy, 1 mi off 85/40

Let’s stay on Peace St

No Car Needed! Close to DT & NCSU! @ VintageModPad
When is the best time to visit Pittsboro?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £91 | £89 | £91 | £88 | £111 | £112 | £110 | £121 | £118 | £96 | £96 | £96 |
| Avg. temp | 5°C | 6°C | 10°C | 15°C | 19°C | 23°C | 25°C | 25°C | 21°C | 15°C | 10°C | 6°C |
Quick stats about holiday rentals with outdoor seating in Pittsboro

Total holiday rentals
Explore 10 holiday rentals in Pittsboro

Nightly prices starting at
Pittsboro holiday rentals start at £30 per night before taxes and fees

Verified guest reviews
Over 1,400 verified reviews to help you choose

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
10 of Pittsboro holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Pittsboro rentals

4.9 Average rating
Pittsboro stays are highly rated by guests – averaging 4.9 out of 5!
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- Duke University
- North Carolina Zoo
- PNC Arena
- University of North Carolina at Chapel Hill
- Wet'n Wild Emerald Pointe Water Park
- Pinehurst Resort
- Raven Rock State Park
- North Carolina State University
- Pine Needles Lodge and Golf Club
- Durham Bulls Athletic Park
- Raleigh Convention Center
- World Golf Village
- Lake Johnson Park
- American Tobacco Campus
- Eno River State Park
- Sarah P. Duke Gardens
- North Carolina Museum of Art
- North Carolina Museum of Natural Sciences
- Greensboro Science Center
- Greensboro Coliseum Complex
- William B. Umstead State Park
- North Carolina Museum of History
- Frankie's Fun Park
- Carolina Theatre




