Vacation rentals in Orange County

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Top-rated vacation rentals in Orange County

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite

A cozy living area features two brown leather sofas with colorful throw pillows, arranged around a black coffee table stacked with magazines. A red area rug adds warmth, while a brick fireplace and doorway to the patio provide visual interest. Natural light illuminates the space.

Home in Hillsborough

4.98 out of 5 average rating, 112 reviews

The Mill House in Hobo, a book lover's retreat.

Welcome to the Mill House in Hobo, an inviting, cozy getaway retreat in historic Hillsborough's west end. Whether you’re coming alone for the solitude or with someone special, this cozy and bright historic mill home in the Bellevue Mill Circle in Hillsborough's eclectic West End offers a peaceful retreat. Looking to house more than 2? Consider the additional rental space accommodating up to 3 more guests and dog friendly found at this Airbnb listing "The Store in Hobo" behind the Mill House.

Top guest favorite

A spacious guest suite features a queen bed with soft white linens, surrounded by elegant wooden furniture. A cozy seating area with two upholstered chairs sits near a decorative fireplace. Light wood floors and built-in shelves create a warm atmosphere, complemented by natural light from large windows.

Guest suite in Hillsborough

4.96 out of 5 average rating, 161 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

A wood-shingled bungalow is nestled among lush greenery, featuring a welcoming front porch with outdoor seating. A cupola crowns the roof, allowing natural light to enter. Flowering plants and ferns line the entrance, enhancing the serene woodland setting.

Bungalow in Chapel Hill

4.97 out of 5 average rating, 459 reviews

Blackwood Mt Bungalow In the Woods with Sauna

Escape to a peaceful hillside retreat nestled in the woods, where the melodies of farm animals and wild birds create a soothing soundtrack. Our stylish and cozy bungalow features three charming porches that invite quiet reflection. Enjoy an easy-to-use indoor compost toilet. Treat yourself to our rejuvenating sauna (+$40) and wander through lush flower and vegetable gardens. While close to town, this getaway promises a restorative escape immersed in nature’s serenity and thoughtful living.

Top guest favorite

A charming cabin features a front porch with two chairs and a small table. The exterior is painted in calming green tones, surrounded by lush trees. A door with a window provides access, while a lantern and potted plants add subtle details to the cozy environment.

Farm stay in Hillsborough

4.92 out of 5 average rating, 159 reviews

Cozy Cabin in the Countryside

Enjoy a cozy cabin with internet, 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 exterior of a two-story orange-clad cabin is shown, featuring a green door and multiple windows. A wooden deck with railing is visible, framed by trees and low shrubbery. The natural surroundings contribute to a tranquil setting.

Guesthouse in Durham

4.87 out of 5 average rating, 220 reviews

Lovely Studio with King Sized Tempur-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, a Roku device to access your streaming apps’ accounts. 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.

Top guest favorite

A petite building constructed from weathered wood stands amidst lush greenery. Unique arched windows and a rustic roof contribute to its character. Soft lighting from within casts a warm glow, creating an inviting scene as the vibrant foliage frames the structure.

Cabin in Hillsborough

4.99 out of 5 average rating, 302 reviews

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.

Guest favorite

The tiny house features a modern design with vertical wood siding and large windows that invite natural light. A spacious deck is visible on one side with seating, and a fire pit area is provided for outdoor gatherings. Surrounding the home are mature trees.

Tiny home in Hillsborough

4.96 out of 5 average rating, 145 reviews

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.

Top guest favorite

The exterior of a carriage house is visible, featuring white siding and a sloped gray roof. A paved driveway leads to two garage doors, surrounded by well-maintained greenery and trees. A portion of a welcoming porch and an American flag can be seen in the background.

Guesthouse in Hillsborough

4.97 out of 5 average rating, 382 reviews

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.

Top guest favorite

A multi-story treehouse, elevated on wooden supports, is surrounded by vibrant autumn foliage. Large windows and a welcoming deck are visible, inviting the outdoor surroundings into the living space beneath a sloping roof.

Treehouse in Hillsborough

4.98 out of 5 average rating, 127 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

The exterior of the tiny house showcases a modern design, featuring a mix of dark wood and light-colored siding. A welcoming front porch with seating invites relaxation, while nearby trees provide a natural setting. Steps lead up to the entrance, enhancing accessibility.

Tiny home in Chapel Hill

4.93 out of 5 average rating, 808 reviews

Chic Modern Tiny House Nestled in the Trees

This 240 sq ft tiny house is 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. Stylish decor, art-filled walls, and a full list of amenities make for a unique and cozy experience of home away from 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

The tiny home is positioned amid a grassy area, surrounded by tall evergreen trees. A vibrant flower bed blooms in the foreground, showcasing a mix of colors against the lush greenery.

Tiny home in Efland

5 out of 5 average rating, 266 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 bright and airy living space features a comfortable white sectional sofa with decorative pillows, positioned beside a round wooden coffee table. In the background, a spacious king bed with neutral bedding is visible, complemented by soft lighting and neutral wall colors.

Guest suite in Hillsborough

4.99 out of 5 average rating, 149 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.