Holiday rentals in Orange County

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Top-rated holiday rentals in Orange County

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Top guest favourite

Guest suite in Hillsborough

4.92 out of 5 average rating, 132 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 favourite

Home in Hillsborough

4.98 out of 5 average rating, 108 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.

Guest favourite

Tiny home in Chapel Hill

4.94 out of 5 average rating, 1,141 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 favourite

Guest suite in Hillsborough

4.96 out of 5 average rating, 152 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!

Guest favourite

Treehouse in Hillsborough

4.97 out of 5 average rating, 167 reviews

Center for Creative Balance cozy treetop retreat

Featured in an issue of Southern Living Magazine, this is a cozy, book-lined, recently renovated space with elegant decor and a wraparound sitting porch, located in a beautiful, mature, piedmont forest abounding with wildlife. There are hiking trails along New Hope Creek and others nearby. Very private and quiet but only 8 minutes from UNC Hospital, Hillsborough Campus, within 20 minutes of Duke, UNC-CH, NCCU, & historic Hillsborough —RDU only 30 minutes. Guests of all walks of life welcome.

Top guest favourite

Cabin in Hillsborough

4.99 out of 5 average rating, 291 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 favourite

Farm stay in Hillsborough

4.9 out of 5 average rating, 126 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

Top guest favourite

Tiny home in Hillsborough

4.97 out of 5 average rating, 133 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.

Guest favourite

Bungalow in Chapel Hill

4.97 out of 5 average rating, 440 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 favourite

Treehouse in Hillsborough

4.98 out of 5 average rating, 121 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 favourite

Tiny home in Efland

5 out of 5 average rating, 252 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 favourite

Guest suite in Hillsborough

4.99 out of 5 average rating, 142 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.