Vacation rentals in Orange County

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Top-rated vacation rentals in Orange County

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Top guest favorite

A wooden bookshelf stands against a neutral wall, featuring three open shelves. A set of clean white towels is neatly placed on the top shelf, while a simple dried flower arrangement adds a touch of decor. Two closed doors frame the bookshelf, contributing to the organized space.

Guest suite in Hillsborough

4.92 out of 5 average rating, 122 reviews

Secluded 2 bedroom MIL apartment w/own yard.

On the end of a road on the end of a road, this MIL suite is connected to my house and is situated on a park like 3 acres. Has a front and back entrance, fenced backyard, picnic table, full kitchen and den area. One bedroom has a queen bed. The other bedroom a single bed. One full bath with nice new 6 foot tub/shower. This place is simple, clean, and ready to go. The space has its own central heat and AC and hot water heater. I rest easy knowing this booking is less expensive than a local motel.

Guest favorite

The exterior of a charming tiny house is featured, showcasing wooden siding with a combination of natural wood tones. A large bay window allows light to enter, while a spacious deck is furnished with comfortable seating. Surrounding greenery enhances the intimate atmosphere.

Tiny home in Chapel Hill

4.94 out of 5 average rating, 1,123 reviews

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

Top guest favorite

Guest suite in Hillsborough

4.96 out of 5 average rating, 146 reviews

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!

Top guest favorite

Cabin in Hillsborough

4.99 out of 5 average rating, 288 reviews

Artist's Studio

Until recently 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.

Guest favorite

Guesthouse in Durham

4.94 out of 5 average rating, 100 reviews

Studio on Tobacco Road

Whether you're coming to work or play, Studio on Tobacco Road is a perfectly positioned launch pad to experience Durham & Chapel Hill. Just 6 miles to Downtown Durham's renowned breweries & culinary scene, experience its creative arts culture & explore its rich history. Minutes from your home court, 4 miles to Duke. 5 miles to UNC. All from a beautifully designed studio on a quiet, nature-rich landscape less than a mile from Duke Forest. Gravel drive was recently paved! Photos to come!

Guest favorite

A screened porch features a dark wicker couch adorned with blue and white cushions, providing a cozy seating area. A natural wood table sits on a woven rug, while wooden beams and a ceiling fan enhance the rustic ambiance, blending harmoniously with the surrounding forest.

Bungalow in Chapel Hill

4.97 out of 5 average rating, 434 reviews

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.

Guest favorite

A hot tub, featuring a smooth, white rim and a dark wooden exterior, is placed on a wooden platform. Steps made of slatted timber provide access to the tub. Surrounding greenery includes trees and grass, enhancing the outdoor setting.

Farm stay in Hillsborough

4.88 out of 5 average rating, 104 reviews

Cozy Cabin in the Countryside

Enjoy a cozy cabin with ac/heat, kitchenette with fridge and microwave. Please note there is no water in the cabin and shower and toilet are located in the bathhouse just a few steps away. This comfortable Cabin has very easy quick access to all amenities including the showerhouse, picnic areas, lawn games, outdoor kitchen. Hottub is open. Property is within minutes of downtown Chapel Hill & Hillsborough, Raleigh, Durham are 20-30 minutes away. No Smoking or Vaping in Cabins.

Guest favorite

The treehouse is illuminated by soft outdoor lighting, standing elevated among tall trees. The structure features large windows, reflecting warm light from within, while the surrounding foliage is tinged with autumn colors in the dusk setting.

Treehouse in Hillsborough

4.98 out of 5 average rating, 117 reviews

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!

Top guest favorite

A close-up view of a wooden wall showcasing delicate flowers arranged on a narrow shelf. Above, a woven pendant light casts a warm glow, complementing the natural wood grain of the wall.

Tiny home in Efland

5 out of 5 average rating, 241 reviews

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

Top guest favorite

A charming two-story house features a covered front porch with seating. The exterior includes light-colored siding and dark roofing, complemented by landscaped areas with flowering plants and greenery. Large windows bring in natural light, creating a welcoming appearance amidst a serene outdoor setting.

Guest suite in Hillsborough

4.99 out of 5 average rating, 137 reviews

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.

Guest favorite

Guesthouse in Durham

4.87 out of 5 average rating, 208 reviews

Lovely Studio with King Sized Trmpur-Pedic

Experience the beauty of Duke Forest in your back yard! Cozy and quiet in the trees, yet 2 miles from Duke University. King sized tempur-pedic for an amazing nights sleep. Our wonderful studio apartment boasts a well-equipped kitchenette, Roku with Hulu, Netflix included. A beautiful, private deck with panoramic views of Duke Forest. Walk right onto Sheperd's Trail, curated by Duke University, from the back yard. 2 miles to Duke Hospital. 3 miles to downtown Durham.

Guest favorite

The dome structure is illuminated from within, showcasing a cozy interior with wooden accents and soft linens. The exterior design features a geometric pattern of clear panels, allowing glimpses of the interior and the surrounding trees in the evening light.

Dome in Durham

4.96 out of 5 average rating, 223 reviews

The Japandi Dome

Experience a taste of Japandi in this dome home, and enjoy the mind and body benefits of being closer to nature with the comforts of indoor amenities. This unique space is built with a full skylight to allow you to sleep under the night sky. Complete with heating and A/C for year-round comfort, a full zen-inspired bathroom, and luxury European bedding. Enjoy your meal around a Japanese inspired floor table with straw mats and meditation cushion for seating.