Pet-friendly holiday rentals in Hillsborough

Top guest favourite

Guest favourite

Modern Downtown Cottage, Mins to UNC

Welcome! Our historic mill house has been beautifully remodeled into a warm, contemporary cottage that matches Carrboro’s funky, free-spirited vibe. Outfitted with a modern, well-equipped kitchen, a large, open living room, three guest rooms, and a lovely fenced in backyard, there’s plenty of space to spread out and hang out. Positioned right off Main Street in a charming, family-friendly neighborhood, you’ll enjoy walking to everything DT Carrboro & Chapel Hill has to offer. UNC UNC Hospitals

Outdoor spaces · Pets · Indoor spaces

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Guest favourite

Cozy Rustic Bungalow Suite Wooded Yard & 2BR/1BA

*Proudly renovated Aug ‘26* Tucked away and attached to my house, the space features a private entrance and back patio with a separate fenced back yard in a wooded backdrop ideal for weary travelers and their dogs. This 500 sq ft in-law suite has rustic charm with real comfort. After more than 3 years of Superhosting the space it now has two beautifully appointed bedrooms (King/Full). The suite includes a redesigned living area, full kitchen, both bedrooms, and a fresh bathroom with a 6ft tub.

Outdoor spaces · Pets · Solo travel

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Guest favourite

Bungalow In the Woods - Close to UNC and Duke

Escape to a peaceful hillside retreat nestled in the woods, where the melodies of farm animals and wild birds sooth the soul. 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 (+$50) and wander through our garden & along wooded paths. While close to town, UNC, Duke and I-40, this getaway promises a restorative escape immersed in nature’s serenity and thoughtful living.

Outdoor spaces · Walkability · Hiking

The Kaleidoscope

Enjoy the sounds of nature when you stay in this unique place. Nestled close to Historic Hillsborough, your front door opens up to a forest with a trail running down to a creek. This newly renovated schoolbus conversion features two skylights looking up into the trees, making it feel open and bright, despite being a small space. The kitchen is fully equipped with pots and cutlery as well as fridges and microwave so you can prepare what you need. A shower and composting toilet installed inside.

Pets · Outdoor spaces · Cleanliness

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Guest favourite

Beautiful Farm stay 2 beds, 2 baths with office

Relax with your partner or bring the whole family to our peaceful 45 acre horse farm. We neighbor the Eno River and are centrally located in Northern Durham only 12 miles from Downtown. Come sit and enjoy our beautiful screened in porch that overlooks 2 scenic ponds and offers some of the best sunsets you’ve ever seen. This newly renovated farmhouse is beautifully decorated with 2 bedrooms, large master (king) and second bedroom (queen), office space has a sleeper sofa for additional guest.

Pets · Outdoor spaces · Grill

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Guest favourite

"Enchanted Forest Garden" A One Bedroom Retreat

A 600 s.f. cottage retreat designed by Robert Phillips. One bedroom, full bath and kitchen, and spacious living room. Ten ft. ceilings and fine architectural details; terraced; fountains nestled in a tree grove on 10 acres with foot paths. 15-20 minutes to Chapel Hill/Carrboro, University of North Carolina; Pittsboro and the Saxapahaw arts community on the Haw River. For a reservation, there is a $30 per trip pet fee for each dog (Sorry, no cats). WiFi: See "Other details to note" below.

Walkability · Pets · Indoor spaces

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Guest favourite

Luxury Retreat on Farm with Pool, Hot Tub, Fishing

LUXlife Best Luxury Country B&B Retreat in NC! 120 acres of peaceful farmland with an in-ground salt-water pool, hot tub, pergola, pastures, farm animals, fresh eggs, streams, woodlands, fishing, and hiking. Private hot tub at rental. The heated, salt-water pool and hot tub are located behind the owner's home. You’ll have total privacy. Wholesale pasture-raised Wagyu beef and lamb available at the farm as well as fishing in the stocked pond. Propane grill and pizza oven on your patio.

Pets · Walkability · Amenities

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Guest favourite

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.

Outdoor spaces · Heating · Location

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Guest favourite

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.

Outdoor spaces · Walkability · Amenities

Top guest favourite

Guest favourite

Carriage House-32 Acre Wooded Lot & Trails & Pond

-private 2015 carriage house in Chapel Hill; less than 2 miles from I-40 -less than 8 miles from UNC; less than 20 minutes from Duke -2 bedrooms with queen, 2 twins & a trundle bed -32 acre private wooded lot with 2 mi. of trails w/ stocked pond -open floor plan - 1000 sq.ft. -fully stocked kitchen w/ fresh eggs -high speed wireless internet -on-site washer and dryer (free) -stairs from ground to apartment -4 vehicles parking spaces -outdoor grill & 2 fire pits w/ Adirondack chairs

Walkability · Outdoor spaces · Nearby

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

Outdoor spaces · Walkability · Layout

Top guest favourite

Guest favourite

Modern Tiny House Near Duke & Downtown

You’ll feel like you’re getting away from it all in this modern, private tiny house in the trees, even though you’re just minutes from Duke, downtown Durham, shopping, and restaurants. It’s the perfect balance of peaceful retreat and city convenience. The home includes all the essentials — full kitchen, laundry, A/C, and high-speed internet — but many guests find themselves spending most of their time relaxing on the screened-in porch, listening to birds, and recharging.

Outdoor spaces · Pets · Cleanliness