Family-friendly vacation rentals in Hillsborough

Find and book unique family-friendly homes on Airbnb

Quick stats about vacation rentals that are family-friendly in Hillsborough

Total vacation rentals
Explore 20 vacation rentals in Hillsborough
Nightly prices starting at
Hillsborough vacation rentals start at G$10,460 GYD per night before taxes and fees
Verified guest reviews
Over 600 verified reviews to help you choose
Pet-friendly vacation rentals
Find 10 rentals that welcome pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wi-Fi availability
20 of Hillsborough vacation rentals include wi-fi access
Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Hillsborough rentals
4.9 Average rating
Hillsborough stays are highly rated by guests—averaging 4.9 out of 5!

Top-rated family-friendly rentals in Hillsborough

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Top guest favorite

A red barn-style exterior is framed by lush green grass dotted with bright yellow wildflowers. Tall trees create a natural backdrop, while the inviting entrance features double doors and large windows. The tranquil setting suggests a peaceful retreat in nature.

Cabin in Durham

The Stable: a peace-filled, creative retreat

Welcome to The Stable - a serene solo respite, artist’s retreat or unique getaway for 1 to 6 registered guests. Close to I-85 & I-40, Duke, NCCU and the downtown Durham scene. Quaint & artsy Hillsborough, funky & fun Chapel Hill/UNC and Carrboro are a short drive. Eno River State Park, hiking & biking trails, and the Mountains to Sea Trail are 2.5 miles away. Full of unexpected details, including an outside labyrinth, The Stable is a comfortable sanctuary for all who want to settle in and smile.

5.0 out of 5 average rating, 333 reviews

Top guest favorite

Guest suite in Hillsborough

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.

4.92 out of 5 average rating, 198 reviews

Top guest favorite

Home in Durham

Duke Forest Zen Treehouse - pool table, decks

Enjoy a unique japanese-inspired custom home just 2 miles from Duke. Ascend through the gated entrance up the winding driveway to your own Zen treehouse retreat perched on the edge of the forest. large custom kitchen with Viking appliances, striking stonework and fireplaces. Outside there is a built-in grill, dining area, and firepit. the downstairs rec room is perfect for families featuring a pool table, movie watching area, and huge enclosed porch. need extra space? book both units!

4.98 out of 5 average rating, 101 reviews

Top guest favorite

A serene outdoor area showcases a rectangular swimming pool surrounded by smooth stone decking. Comfortable lounge chairs are positioned for relaxation, while lush greenery and trees provide a natural backdrop. The exterior of the multi-level house features large balconies and a welcoming red door.

Guest suite in Hillsborough

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!

4.96 out of 5 average rating, 196 reviews

Superhost

Camper/RV in Hillsborough

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.

4.83 out of 5 average rating, 155 reviews

Top guest favorite

Three horses of varying colors are seen standing near a wooden fence in a spacious pasture. A covered shelter is located in the background, while a clear blue sky with scattered clouds accentuates the serene landscape.

Farm stay in Hillsborough

Horse farm, serene, secluded, creekside suite

Welcome to Strouds Creek Farm. Charming 2BR 1 bathroom suite w/cozy farmhouse decor. Located on 20 picturesque acres nestled in the woods. Enjoy peaceful mornings filled with bird songs. Stroll around the farm to meet & greet our "fur family". Relax in a hammock, explore the creek or sit on the swing & enjoy the farm fresh air. Just 5 minutes from downtown Hillsborough, an artist's paradise, dotted with art galleries, boutiques, a bookstore & restaurants. 15 min. to Duke & downtown Durham.

4.91 out of 5 average rating, 145 reviews

Top guest favorite

A wraparound porch is featured with large glass doors, providing a view of the surrounding forest. Two black chairs and a potted plant are arranged on a wooden deck, while natural light filters in through a slanted roof.

Treehouse in Hillsborough

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.

4.97 out of 5 average rating, 185 reviews

Top guest favorite

A tranquil salt-water pool is surrounded by lounge chairs and vibrant red umbrellas. A pergola with seating is visible in the background, along with well-maintained landscaping and an inviting patio area. The clear blue sky enhances the serene environment.

Farm stay in Hurdle Mills

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.

4.98 out of 5 average rating, 229 reviews

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

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.

4.99 out of 5 average rating, 335 reviews

Top guest favorite

Home in Hillsborough

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.

4.98 out of 5 average rating, 122 reviews

Top guest favorite

An outdoor fire pit area features four black Adirondack chairs arranged around a stone circular base. The carriage house, painted in rich red, serves as a rustic backdrop, with greenery and flower beds enhancing the inviting environment.

Farm stay in Chapel Hill

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

4.99 out of 5 average rating, 613 reviews

Top 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

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.

4.96 out of 5 average rating, 206 reviews