House holiday rentals in Hillsborough

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Top-rated house rentals in Hillsborough

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Guest favourite
A two-story house is presented in a neutral color with white trim and black shutters. The front porch features a welcoming entrance and steps leading to the door. Surrounding trees provide a natural backdrop, and a driveway offers access to the property.
Home in Woodcroft
4.87 out of 5 average rating, 150 reviews

Charming home betw. Duke & UNC with wooded trails

Relax with the whole family at this peaceful home between Duke and UNC, in one of the triangle's best neighborhoods. Woods everywhere, yet close to dining and shopping, coffee shops and farm stands. Just a six mile drive to Duke, UNC, and RTP, so literally in the center of everything, yet so peaceful! Enjoy modern kitchen, fireplace, fiber Internet & great outdoor spaces! We are glad to host you and we live right down the street, so come and relax and let us know if you need anything at all.

Top guest favourite
Home in Chapel Hill
4.95 out of 5 average rating, 180 reviews

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.

Guest favourite
A spacious living area features a sleek gas fireplace on one side, with modern artwork displayed on the walls. Comfortable seating includes a large gray sofa and green accent chairs, accompanied by a round coffee table. Natural light floods in through large windows.
Home in Old North Durham
4.95 out of 5 average rating, 99 reviews

Modernist Masterpiece: 'Simply the Best'

Welcome to Hazel Modernist 6 - designed and built by Alicia Hylton-Daniel, with her "sister," Modernist 5, next door. Centrally located downtown, this gorgeous escape is truly livable. Fully equipped chefs kitchen opens into the large living & dining space, with Frame TV and fireplace. 3BR & private back deck offer plenty of space together or alone. Each home by Alicia is infused with creative and new design concepts. This glamorous home celebrates the essence of Tina Turner, Simply the Best.

Guest favourite
Home in Durham
4.98 out of 5 average rating, 133 reviews

Luxury Modern Suite W/ Private Deck

Welcome to our Private Luxury Master Suite! Enjoy a hotel-like experience with a spacious luxury bath featuring double sinks and a rain shower and a beautiful private deck with a peaceful view. We also include a coffee bar, work area, Wi-Fi, and TV. Conveniently located from RDU Airport and Downtown Durham, with a variety of restaurants and coffee shops nearby. Experience the perfect blend of comfort, luxury, and convenience in this upgraded suite! Parking is available and limited to 1.

Top guest favourite
A single-story home with a spacious patio is surrounded by greenery. The exterior features a stone pathway leading to the entrance. Large windows with yellow shutters allow natural light to brighten the interior. A gravel driveway accommodates multiple vehicles.
Home in Chapel Hill
5 out of 5 average rating, 167 reviews

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!

Top guest favourite
A bright living area features large two-story windows that allow natural light to fill the space. Wooden walls complement modern furniture, including two armchairs and a glass coffee table. A cozy throw blanket is draped over a spacious sofa, adding warmth to the inviting atmosphere.
Home in Chapel Hill
4.99 out of 5 average rating, 98 reviews

The Dragonfly

Summer 2025 dates available! We have a short window of availability between long-term stays. Come enjoy stunning views and fresh figs at The Dragonfly in August and September. ——- Serene and private luxury just minutes from UNC Chapel Hill. Two-story windows flood the house with natural light and provide gorgeous wooded views. Soak in your natural surroundings from a sprawling back porch and two additional private decks. Where else can you see all the stars in the heart of the Triangle?

Top guest favourite
A spacious living area features large glass walls allowing natural light and views of surrounding trees. A unique wood coffee table is centered on a light rug. Two comfortable sofas provide seating, paired with a modern lamp and elegant decor.
Home in Raleigh
4.95 out of 5 average rating, 169 reviews

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.

Guest favourite
The exterior of a renovated single-story home is presented, featuring a neutral color palette and a well-maintained yard. A front porch with black railings is visible, alongside inviting landscaping. A gravel driveway leads to the entrance, surrounded by trees providing a natural backdrop.
Home in Durham
4.93 out of 5 average rating, 121 reviews

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.

Guest favourite
A modern kitchen features white cabinetry with stainless steel appliances and granite countertops. A round glass dining table surrounded by four black chairs is positioned on a light rug, enhancing the space's contemporary feel. Natural light filters in through the nearby window.
Home in Chapel Hill
4.88 out of 5 average rating, 103 reviews

Jo Mac Cottage- Quiet Home near UNC Chapel Hill

Welcome to the beautiful 100 year old Jo Mac Cottage in Chapel Hill We are minutes away from Chapel Hill and Carrboro. The house provides plenty of privacy in a quiet neighborhood and provides plenty with trees all around. We are 10 minutes away from UNC Campus! You can also enjoy the great outdoors by visiting local attractions such as Lavendar Oaks Farm or Rock Quarry Farm! Looking for more excitement, head down to Franklin Street for plenty of great food options.

Guest favourite
A comfortable living area features a dark blue sofa and a light-colored armchair, complemented by decorative pillows. A coffee table rests on a patterned area rug, while a television is positioned on a wooden stand. Natural light enters through a window dressed with light curtains.
Home in Durham
4.87 out of 5 average rating, 208 reviews

CHARM & Convenience!! 3Br Cottage-Style Ranch

This home is located in the more DESIRABLE and 'not as congested' low crime area of Durham near Chapel Hill, on a half acre lot in the rural buffer zone! You're really convenient to Duke Hospital/Duke campus, and also just a very short drive to Chapel Hill! The backyard is BIG and completely fenced in for family games or just enjoying the birds, or your dog's exercise! Duke Forest trails and New Hope Creek are VERY nearby for a wonderful hike during your stay.

Guest favourite
A wooden cabin is nestled among lush green trees, surrounded by a natural landscape. A winding path leads to the entrance, lined with simple outdoor lighting. The tranquil setting is embraced by the vibrant foliage, creating a peaceful retreat atmosphere.
Home in Chapel Hill
4.91 out of 5 average rating, 129 reviews

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.

Superhost
The living room is illuminated by natural light through large windows, showcasing a comfortable seating area with a sofa and stylish armchairs. A piano is positioned nearby, complemented by wall art and a decorative rug on the wooden floor.
Home in Durham
4.9 out of 5 average rating, 187 reviews

Cheerful 2-bedroom home in quiet cul de sac

Bright and lovely duplex nestled away in a quiet cul de sac. Duke and downtown are reachable in minutes, and there's a Harris Teether within walking distance. Enjoy the outdoor space, or relax in the living room sorrounded by art and music. Accessibility: The sidewalk and entryway are not wheelchair accessible, guests using wheelchairs may need assistance.

Popular amenities for house rentals in Hillsborough

Quick stats about house rentals in Hillsborough

  • Total holiday rentals

    Explore 10 holiday rentals in Hillsborough

  • Nightly prices starting at

    Hillsborough holiday rentals start at $90 SGD per night before taxes and fees

  • Verified guest reviews

    Over 510 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space & child-friendly amenities

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    10 of Hillsborough holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Hillsborough rentals

  • 4.8 Average rating

    Hillsborough stays are highly rated by guests – averaging 4.8 out of 5!