Family-friendly holiday rentals in Orange County

Timberwood Tiny Home

Timberwood Tiny Home is a place to rest your head & heart in Efland, North Carolina. The peaceful retreat 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 more. There are features of the home that may make it unsuitable for children.

Charming Tiny House Nestled in the Trees

This small 128 sq ft tiny house is packed with charm. Situated on a serene 5 acre wooded property, its a short drive to Hillsborough (10 min), Chapel Hill (15) and Durham (15). I wanted to create a space where guests can take time to rest and reset. The house is cozy, stylish, and surprisingly spacious. Its well appointed with all the amenities to feel like home. Take a step outside and you'll be surrounded by old hardwood trees and the soothing sounds of nature that make life here so peaceful

The Kaleidoscope

Enjoy the sounds of nature when you stay in this unique place. Nestled close to Historic Hillsborough, your front door opens up to a forest with a trail running down to a creek. This newly renovated schoolbus conversion features two skylights looking up into the trees, making it feel open and bright, despite being a small space. The kitchen is fully equipped with pots and cutlery as well as fridges and microwave so you can prepare what you need. A shower and composting toilet installed inside.

Luxe Guest Suite w Pool (Historic, Downtown)

Southern charm is in abundance in this c. 1799 home! This sun-filled, artfully restored space is a private, "in-law" suite adjacent to a sprawling southern Estate. You'll enjoy a private entrance, huge living area / queen bed, large dressing room with "his and hers" vanities, modern bathroom with walk-in shower and oversized tub, access to gorgeous pool, and sprawling verandas. The space is mere blocks from all that quintessential historic Hillsborough has to offer, and is a rare treasure!

Horse farm, serene, secluded, creekside suite

Welcome to Strouds Creek Farm. Charming 2BR 1 bathroom suite w/cozy farmhouse decor. Located on 20 picturesque acres nestled in the woods. Enjoy peaceful mornings filled with bird songs. Stroll around the farm to meet & greet our "fur family". Relax in a hammock, explore the creek or sit on the swing & enjoy the farm fresh air. Just 5 minutes from downtown Hillsborough, an artist's paradise, dotted with art galleries, boutiques, a bookstore & restaurants. 15 min. to Duke & downtown Durham.

Center for Creative Balance cozy treetop retreat

Featured in an issue of Southern Living Magazine, this is a cozy, book-lined, recently renovated space with elegant decor and a wraparound sitting porch, located in a beautiful, mature, piedmont forest abounding with wildlife. There are hiking trails along New Hope Creek and others nearby. Very private and quiet but only 8 minutes from UNC Hospital, Hillsborough Campus, within 20 minutes of Duke, UNC-CH, NCCU, & historic Hillsborough —RDU only 30 minutes. Guests of all walks of life welcome.

The Chapel Hill Forest House

Book this incredible tiny house for the perfect romantic getaway in the heart of Chapel Hill! It sits in a private forest full of wildlife but is only a 5-minute walk to Franklin Street and the UNC campus. Enjoy amazing views from the floor-to-ceiling windows of foxes and deer playing on the lawn. Lounge on the wall-to-wall hammock as you gaze at the trees through the skylights. Unwind with a movie in bed played on our massive projector. There's nothing like this anywhere in the Triangle!

Artist's Studio

Originally the studio of a visual artist (long ago garden illustrator for The New York Times), this petite building is completely private. Firm queen bed. Mix of antiques and artisanal built-ins. Radiant heat. AC. Mini fridge and microwave, electric kettle, Chemex coffee maker and French Press, excellent wifi. Unique space in one of the best country neighborhoods around. 6.5 miles to Hillsborough healthy grocery store, 8 to Carrboro/Chapel Hill, 18 to Durham. Serene pond and grounds.

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

Peaceful tiny house retreat on 30 acre farm

This new tiny house is nestled amongst mature hardwood trees on a 30 acre working family farm in Hillsborough. Quiet your mind and restore your body in the luxurious hot tub or warm up by the cozy fire-pit. Under 10 miles to Hillsborough or Durham, and their many restaurants, breweries and shops. Enjoy the privacy of two secluded wooded acres, surrounded by the sights and sounds of our farm, where we are growing fruits, veggies and mushrooms & caring for our animals and pastures.

The Magnolia

The Magnolia is a multi-story treehouse, nestled on a charming wooded lot, minutes to downtown Hillsborough, NC. Built in the treetops, this bright and airy space is full of handmade touches and warm wood tones. Enjoy your tea or coffee on the second story deck for two, relax in the cozy loft bedroom with views of the forest, prepare meals in the kitchen for a night in, and wrap up your day beside the outdoor fire pit and water garden. We can't wait to have you at The Magnolia!

Charming Downtown Hillsborough Cottage

Enjoy all Hillsborough has to offer in this recently renovated and pet-friendly charming cottage in historic downtown! Whether you’re coming alone or with a friend, this cozy and bright home has everything you need. Easily walkable to the restaurants, galleries, and shops of downtown historic Hillsborough and Nash St. For nature lovers, Gold Park, the Eno Riverwalk, and Occoneechee Mountain are all just around the corner. Centrally located for access to Duke, UNC, and NCCU.