Holiday rentals with outdoor seating in Chatham County

Shepard Farm

Secluded and peaceful, the name of the street says it all: Sunset. This gated residence offers breathtaking sunset views across a sprawling 50 acre farm. Take in the landscape, complete with horses & cows, or retire to your exclusive guest house, complete with full kitchen, refrigerator, and washer & dryer. This guest house has a king bed & queen sofa bed, and comes with your own gate & door codes, parking space, and private, fenced-in back yard for your furry friends (pet fee applies).

Curiously Cute B&B: Woodshed Unit

This refurbished container building built by an architect professor @ UNC Charlotte for a traveling art exhibit. This fabulous space has a queen bed, single futon, private bath & deck overlooking gardens w/ outsider folk art scattered about property. Mini fridge (holds 15x 12oz cans), coffee station w Starbucks Kcups & smart TV for streaming. Pass for FREE tasting @ Fair Game Distillery Included! Rates SINGLE OCCUPANCY add’l $20/person/night. Hammock, picnic tables, playground & firepit

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.

Awesome Fearrington Village Suite, historical

Tradition continues, this is a multi-generational home dedicated to family and travelers alike since 1984. Janet's parents, Audrey and Elmo Jones created this 1,100 square foot fully appointed, fragrance and pet free upper suite which utilizes a stairway. Many guests have discovered Fearrington Village which is less than a half mile stroll away. Wooded hiking trails intertwine all of Fearrington Village. We look forward to providing you with safe housing during your stay with us.

Lovely farm cabin experience

Connect with nature in this unforgettable farm setting. Take in serene views from the deck or walk around to enjoy a variety of sweet animals including sheep, horses, goats, alpacas, emus, cows, ponies and more. The space is a fully furnished apartment in an adorable stone cabin with one queen bedroom, kitchen, full bath, laundry, high speed Wi-Fi, and outdoor hot tub. Upper cabin is also available as a separate rental (sleeps 5) listed as Log Cabin at the Farm on Airbnb.

Whimsy Cottage Close to Everything in Pittsboro

Charming 2-bedroom, 1-bathroom, Boho Elegant 1927 Bungalow in the heart of Pittsboro West. Step off the large front porch and head across the street to a local craft brewery, shopping, a delicious bakery serving breakfast and lunch and Chatham County Community College with a public library and paved walking trail. Walking distance to great bars, shops and restaurants in downtown Pittsboro. Whimsy on West is the perfect home away from home for any reason!

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 bedroom + private loft with 2 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!