Holiday rentals with outdoor seating in Pittsboro

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.

Timberwood Tiny Home

Timberwood Tiny Home is a place to rest your head & heart in Efland, North Carolina. The peaceful retreat, designed for adults only, is down a country road approximately 10-minutes from downtown Hillsborough. The 200 square foot tiny home is on a private corner of 8-acres shared with our main house. It features Scandinavian-style details, two beds, a spacious porch, abundant natural light, a wood-fired hot tub, barrel sauna, cold plunge, and much more. @timberwoodtinyhome

Gorgeous Retreat - Close to CH/Carrboro/Saxapahaw

Welcome to our cozy craftsman guest suite! Private and peaceful - we're situated on 5 acres close to Carrboro/Chapel Hill (13 mi), UNC Hospitals (15 mi), Elon (20 mi), and the charming Village of Saxapahaw (5 mi). The guest suite is a spacious 500 sq ft with private entrance, full kitchen and bath, bedroom, and living area. With views into the woods and garden, it's a beautiful spot to get away, relax, and enjoy nature. Great for couples and solo travelers alike.

Cozy Secluded Accessible West Wing

The West Wing is guest quarters to a residence on 15 acres 5 miles south of Chapel Hill. It's an easy 10 minutes (5 miles) to downtown Chapel Hill, UNC, UNC Hospitals and Carrboro. Comfortable, clean, attractive, and very secluded. It is a studio apartment with one double bed, perfect for one person, cozy for two.. Your friendly, well behaved dog is welcome, but don't ever let your dog on the furniture or leave your dog alone uncrated. Sorry, no cats.

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!