Vacation rentals 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 one big room guest house has a king bed & queen sofa bed, and comes with your own door code, parking space, and private, fenced-in back yard for your pets. (pet fee applies).

Eclectic & Spacious Guest Cottage

Eccentric décor & art adorn the Guest Cottage walls and outsider art is scattered about the gardens. This handicap accessible unit has a king sized bed and a queen size Murphy bed, living room, kitchenette with coffeemaker, 2 burner cooktop, microwave, toaster oven & minifridge w/ freezer compartment. By the front door, is a small patio with vintage lawn furniture (seats 4) and a coffee table. Rates are TRIPLE OCCUPANCY An additional $20/ person/night applies. Pet friendly w/ pet fee.

"Enchanted Forest Garden" A One Bedroom Retreat

A 600 s.f. cottage retreat designed by Robert Phillips. One bedroom, full bath and kitchen, and spacious living room. Ten ft. ceilings and fine architectural details; terraced; fountains nestled in a tree grove on 10 acres with foot paths. 15-20 minutes to Chapel Hill/Carrboro, University of North Carolina; Pittsboro and the Saxapahaw arts community on the Haw River. When making a reservation there is a $30 per trip pet fee for each pet. WiFi: See "Other details to note" below.

Remodeled home in the country "Staley's Secret"

I am always tweaking decor and amenities, the home is very functional. built in 1958, so keep that in mind before booking. please inquire any special needs prior to to booking. you can take it easy at this unique and tranquil getaway. Convenient to Cary, High Point, Greensboro, Asheboro. Lots of attractions, restaurants, entertainment. Quiet, light traffic. Hardwood floors throughout home. There is much more to come, so i hope you will be my guest many times along this journey.

Piece of Heaven Airbnb, Wedding, and Event Center

Our Home is Set on 100 acres of Pines , a Mile From Stress, and The Rocky River as a back drop, This Piece of Heaven is waiting for you. ( please note we allow for wedding and other events but those charges are not included with an Airbnb rental) Our 150+ yr old home is modernized uniquely to bring nature closer with 1700 sq ft of deck space, and a River View deck that is so peaceful. If you are thinking Event/ Wedding, we would love the opportunity to earn your business.

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!

Restored Cabin on Heritage Farm.

Built in the 1930's from a Rehoboth Beach cabin design; the "Clubhouse" was built for out-of-town city guests to get a little peace and quiet in rural NC. Newly refurbished, family friendly, with plenty of forested land for exploring, camper/trailer parking and fenced pasture with water. Free wi-fi. Pets welcome - two pet limit. Pasture may be suitable to horses who won't jump the fence and can get along with 3-4 heifers.

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!

Second Home in Pittsboro, NC

This newly remodeled home is on 4 wooded acres in Pittsboro. It is one mile from Chatham Park, and close to the downtown shops and restaurants. It is convenient to drive to Jordan Lake, Fearrington Village, Chaple Hill, Apex, and Cary. Chatham County is one of the fastest growing in the state, but Pittsboro retains it's historic and eclectic roots. We are pet-friendly, with a fenced in backyard.

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

The Bower: magical place in the woods

Write your book, renew with your partner, slow down and unwind in a safe, soulful place. Special features of this place include over a hundred acres of woods with well maintained trails and two creeks. We also have a wood burning sauna you can use. We love when folks can enjoy this beautiful land and reconnect with what truly nourishes.