Holiday rentals in Orange County

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!

Downtown Hillsborough Luxury Retreat #5

Brand new fully equipped retreat tucked away on a quiet street. Located in the vibrant downtown historic district of Hillsborough. Enjoy the beautiful scenery, architecture, restaurants/ bars and the lively arts and culture scene. From art and river walks to live music as well as farmers markets and festivals. Top of the line appliances, quality mattresses, luxury modal sateen linens, washer/ dryer, grills with propane, front & back balconies and complimentary parking in the rear of building.

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.

Hummingbird Retreat

Airy and open, private and quiet! Come get away from it all and still be a short drive to all that the Triangle has to offer! High quality cottage style carriage house loft with full bath & private entrance - luxurious king-sized bed, Bonavita coffee maker, and handy microwave and mini fridge. Located just 4 miles south of hip and historic downtown Hillsborough in a rural, wooded country setting. Close access to Duke, UNC Chapel Hill; and Elon University is 27 miles west on I40.

Blackwood Mt Bungalow In the Woods with Sauna

A peaceful place, perched on a hillside in the woods, with sounds of farm animals and wild birds. The Bungalow is stylish and comfortable, with a large triangular window, king-sized bed, well-stocked galley kitchen, indoor COMPOST TOILET, indoor shower, and three different porches. Don't miss our SAUNA experience! In the yard, we have flower and veggie gardens, wood-fired PIZZA OVEN and nearby hiking trails. Our lifestyle embraces beauty and sustainability through permaculture.

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!

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

Private suite with kitchenette. Walk to downtown!

Enjoy this new private suite in downtown Hillsborough with separate entrance. We are a 1/2 mile to restaurants and shopping on Churton Street. King bed, Full bath, kitchenette with microwave, Keurig coffee maker, tea kettle, wifi, Roku TV, small refrigerator, sitting area, and workspace. Truly a unique and comfortable place to stay. Enjoy wine and coffee on the front porch or visit the local downtown coffee shops and restaurants. Our space is best suited for adults.

Private 530sqft Family Friendly Suite

Come stay in our private suite on the lower level of our home! We have a great location only 9 minutes drive to UNC and easy access to I-40 gets you to RDU and the airport easily. We provide high speed internet with ethernet hookup and mesh wifi with a dedicated workstation. Large flatscreen TV includes at least 3 streaming services and our personal digital movie library through Apple TV app. Fully stocked Keurig station with coffee, tea and the morning basics!