House holiday rentals in Hillsborough

1920s Historic Retreat in Downtown Graham

Step into a refined home where history & comfort meet. Built with enduring charm and restored with care, this elegant heritage retreat blends period details with modern indulgences - crafted for guests who appreciate quality in every detail. Whether you're preparing a casual breakfast or hosting a family gathering, our gourmet kitchen is fully equipped for culinary creativity. You'll find premium cookware, an induction cooktop for quicker meal prep, and ample space to cook, connect, and savor.

Mid-Century Gem • Creekside • King Beds • Near UNC

This curated 3BR/2BA mid-century modern Chapel Hill home blends comfort, style, and nature in perfect harmony. Designed by renowned local architect JP Goforth, the home sits on a wooded acre with a private creek and features king beds in every room, Sonos audio, and fiber WiFi. Relax on the deck, fire up the grill, or unwind inside surrounded by stunning hand-selected art and furnishings. Minutes from UNC, Whole Foods, and Eastwood Lake, it’s a true retreat for anyone craving serenity and style.

Artist-Designed Cabin Near Duke & Downtown

Relax and recharge in a modern, artist-designed passive solar home tucked into the woods just minutes from downtown Durham and Duke University. This cabin-style retreat blends nature, comfort, and convenience — ideal for weekend getaways, visiting Duke, or extended stays. Inside you’ll find original artwork, abundant natural light, and a professionally equipped kitchen. Outside, enjoy birdsong and mature trees while staying close to Durham’s restaurants, coffee shops, breweries, and shopping.

Modern Spacious Tiny Home Nestled in the Trees

Nestled amongst 5 acres of hardwood trees, this small yet spacious home is a great place to retreat and unwind. I built this home for myself over the course of a couple years and put all my love into every part of the design. I occasionally travel and would love to share the space with you while I'm away. The house is modern yet is full of warmth. Every window offers a view of the forest around the house. It's the perfect base for a visit, within a 15 min drive of CH, Durham and Hillsborough

White Oak Hill, minutes to UNC & Duke

Have everything you need for a hassle-free Chapel Hill/Carrboro retreat at this perfectly appointed home just 6 miles west of the city. Newly remodeled to please with luxury finishes inside and out, this vacation rental is highlighted by serene and beautiful country views from every window. This spacious layout sleeps 10 with 4 bedrooms, 2 full bathrooms, 1 half bath, 2 living rooms, bar seating and separate dining room. Foodies will love cooking in the fully equipped gourmet kitchen!

Warm and Welcoming 3-Bedroom Cottage

Welcome to Carolina Cottage, nestled in one of Durham's premier post WWII neighborhoods, and extensively renovated by Designer + Builder Alicia Hylton-Daniel. Your experience will be enhanced by the thoughtfully curated spaces for relaxing, renewing and re-connecting. The home is spacious, with common areas to be shared, inside and out, as well as quiet spaces to read, nap, scroll and stream. You'll enjoy a full chef's kitchen and dining room, along with a sunny porch and shaded patio.

Luxurious Modernist Tree House

Stunning, private, and truly one-of-a-kind—this unique home is perfect for a vacation, staycation, special occasion, or simply celebrating everyday life. Designed by renowned modernist architect Frank Harmon. The 2,128-square-foot residence sits on 1.3 acres and was crafted with meticulous attention to detail. Inside, you’ll feel nestled among the treetops while remaining conveniently close to restaurants, shopping, downtown Raleigh, WakeMed, UNC, Duke, and Research Triangle Park.

Walk to Downtown Hillsborough • Dog Friendly

More than just a vacation rental, this is a home we love and are happy to share. Tucked into a quiet, walkable neighborhood near historic downtown Hillsborough, you can walk to restaurants, coffee shops, galleries, Gold Park, the Riverwalk, and the Eno River, then come home to relax on the porch or in the fenced backyard. Thoughtfully stocked for comfortable everyday living, it’s ideal for weekend getaways, weddings, family visits, and trips to Duke or UNC. Dogs are welcome, too.

Newly Renovated 3 BR home in convenient location!

Newly renovated space to relax and explore the best of Durham. Sleeps 6 with plenty of space to spread out. Well located - only 10 minutes to Duke, Duke Hospital, downtown and Ninth/Broad Street areas. Enjoy use of the fully stocked kitchen, comfortable living area, dining space and spacious back deck and screened in porch. Grill out and enjoy the back yard. Great for families and groups of friends or business travelers. Several restaurants close by and easy access to highways.

Lakefront Hygge: Dock|Marine Hammock|Screen Porch

Discover a peaceful haven on the water in Prospect Hill! This stylish Scandinavian Modern house boasts a private dock on a quiet reservoir, offering a serene escape. Enjoy the natural beauty and tranquility, while still being a short drive to Hillsborough, Chapel Hill, Durham, Raleigh, Greensboro, Charlotte and Danville. With a cozy, inviting interior, and abundant places to enjoy the outdoors, this waterfront property is the perfect place to "press pause".

Retreat to Historic Home in a Private Arboretum

Unwind and renew your spirit in our updated 5 bedroom (sleeps 9) historic house (circa 1830's) in the heart of the largest arboretum of its kind in the USA. Explore our exotic 206 acre property sheltering 4000 different North American and international tree species. Hike through old growth forest past historic outbuildings and watch the sun sparkle on our ponds. We are family and pet friendly, 25 minutes to Duke University, 17 minutes to UNC Chapel Hill.

Calming Woodland Octagon

Take a much needed break from the stresses of the city at this unique property nestled in old growth woodland. Indulge in the sound of the wind and a sea of stars. Make friends with your neighbors: deer, squirrels, hawks and fireflies. A haven for writers, artists, dancers, remote workers and nature lovers only 15 minutes from Chapel Hill and 8 minutes from Jordan lake. You'll find Zen, fiber internet, and more than a little magic here.