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Vacation rentals in Hillsborough

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Quick stats about vacation rentals in Hillsborough

  • Total vacation rentals

    Explore 50 vacation rentals in Hillsborough

  • Nightly prices starting at

    Hillsborough vacation rentals start at G$8,368 GYD per night before taxes and fees

  • Verified guest reviews

    Over 2,730 verified reviews to help you choose

  • Family-friendly vacation rentals

    20 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wi-Fi availability

    50 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 vacation rentals in Hillsborough

Guests agree: these stays 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.

LocationValueAmenities

5.0 out of 5 average rating, 333 reviews
Top guest favorite
Home in Hillsborough

The Farmhouse at Spring Forest

This stylish home on a working farm is a beautiful and comfortable place, perfect for group trips. Nestled in the North Carolina Piedmont minutes from Raleigh, Durham, and Chapel Hill, the Farmhouse offers a serene setting for groups looking for a retreat or a family gathering . Trails through a mature forest, gorgeous views of crops and livestock, and access to a pool (May - September) all add to the ambience. The back patio with grill and fire pit area are perfect for gathering with friends.

FamilyLocationBathroom

5.0 out of 5 average rating, 24 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.

ValueFamilyLayout

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!

ValueFamilyLong stay

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!

FamilyLocationParks

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.

ValueLocationCleanliness

4.83 out of 5 average rating, 155 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.

FamilyValueLayout

4.97 out of 5 average rating, 185 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.

ValueFamilyComfort

4.91 out of 5 average rating, 145 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.

LocationFamilyIndoor spaces

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.

FamilyValueNearby

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

ValueLocationIndoor spaces

4.99 out of 5 average rating, 613 reviews
Top guest favorite
An outdoor barrel sauna is nestled amidst lush greenery, constructed of natural wood with a curved design. A large glass door provides entry, while a wooden platform with a bucket sits outside, inviting relaxation in a serene environment.
Guesthouse in Chapel Hill

Cozy Sauna Retreat - Woodland Guesthouse

Private and peaceful guest house tucked away in the woods just outside of Carrboro - Relax in an outdoor barrel sauna + enjoy the stars by the fire pit - Sleep in a King Bed or a Queen Pull-out couch in the living room for extra guests - Cook in a full kitchen and enjoy your meals inside or dine al fresco with the fire pit - Stay active with the dedicated workout area Minutes from the best restaurants & breweries 13 minutes to UNC Chapel Hill 23 minutes to Duke University

FamilyLocationCleanliness

5.0 out of 5 average rating, 105 reviews

Popular amenities for Hillsborough vacation rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Stay near Hillsborough's top sights

Occoneechee Mountain State Natural Area

79 locals recommend

Yonder

16 locals recommend

Nash Street Tavern

9 locals recommend

Other great vacation rentals in Hillsborough

Guest favorite
Home in Hillsborough

The Gathering House at Elevated Escape

FamilyLocationComfort

5.0 out of 5 average rating, 5 reviews
Guest favorite
Home in Hillsborough

Perfect Family Country Getaway Kid/Pet Friendly

LocationFamilyLaundry

4.9 out of 5 average rating, 73 reviews
Top guest favorite
The farmhouse exterior is showcased in natural light, highlighting the white siding and multiple windows. A spacious deck is visible, flanked by tall trees and greenery. The two-story structure features a chimney, contributing to its classic farmhouse aesthetic.
Home in Hillsborough

Cozy farmhouse with beautiful lake views

FamilyLocationCheckout

4.89 out of 5 average rating, 38 reviews
Guest favorite
A spacious deck, surrounded by lush greenery, features a charming gazebo with a peaked roof and seating. Adjacent to it, a Finnish barrel sauna is visible, offering an inviting space for relaxation amid the tranquil forest setting.
Home in Hillsborough

NEW! Peaceful Retreat, Spa/Sauna [Entire Property]

FamilyValueIndoor spaces

4.92 out of 5 average rating, 89 reviews
Top guest favorite
Guest suite in Hillsborough

Pet-Friendly 1-Level | WFH Space | 5 Min to Town

LocationValueKitchen

5.0 out of 5 average rating, 17 reviews
Top guest favorite
A yellow cabin exterior features large glass doors framed by a deep blue entryway. Two dark wicker chairs and a small table sit on the wooden deck, surrounded by greenery. A decorative window above the door adds a touch of character.
Tiny home in Hillsborough

Little House in W. Hillsborough

ValueFamilyComfort

5.0 out of 5 average rating, 76 reviews
Top guest favorite
A serene lake view captures a vibrant sunset, with the sun dipping below the horizon and casting warm reflections on the water. Fluffy clouds stretch across the sky, adding texture to the tranquil scene, while greenery outlines the waterfront.
Cottage in Cedar Grove

Cottage on the Lake

FamilyLocationLong stay

5.0 out of 5 average rating, 63 reviews
Top guest favorite
A welcoming open-concept living area showcases a comfortable sofa adorned with colorful throw pillows. Natural light fills the space, highlighting the wooden flooring and the dining area in the background. A TV is mounted on the wall, with decorative accents enhancing the aesthetic.
Home in Hillsborough

Modern Cozy House In The Heart Of Hillsborough

LocationValueBathroom

4.96 out of 5 average rating, 73 reviews

When is the best time to visit Hillsborough?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$26,150 GYDG$24,895 GYDG$26,150 GYDG$26,569 GYDG$27,406 GYDG$26,150 GYDG$26,778 GYDG$28,243 GYDG$28,243 GYDG$29,289 GYDG$27,824 GYDG$26,569 GYD
Avg. temp5°C6°C10°C15°C19°C23°C25°C25°C21°C15°C10°C6°C

Frequently Asked Questions

  • What are the best places to stay in Hillsborough?

    Historic neighborhoods near downtown have charming homes, while wooded areas and riverfront cottages offer quiet retreats. Many vacation rentals are close to parks, trails, and local dining spots.

  • What are the best things to do in Hillsborough with kids?

    Families explore the Riverwalk for riverside walks, visit local playgrounds, or learn about the area’s past at the Museum of History. Picnic spots and small festivals often create a relaxed atmosphere for children.

  • What are some of the best things to do in Hillsborough?

    Walk the Riverwalk along the Eno River, browse galleries in the historic downtown, or visit Occoneechee Mountain State Natural Area. Farmers markets and local cafes reflect the area’s creative community.

  • How is the weather in Hillsborough?

    Hillsborough has cool winters between 30–50°F (-1–10°C), with occasional rain, and warm, humid summers around 63–88°F (17–31°C). Spring and fall tend to be milder with pleasant weather for outdoor activities.

  • When is the best time to visit Hillsborough?

    Spring and early fall are often recommended for outdoor exploring in Hillsborough, featuring mild temperatures around 60–80°F (16–27°C) and colorful scenery. These seasons also bring community events and local gatherings.

  • What are the best places to visit in Hillsborough?

    The Riverwalk, Occoneechee Mountain State Natural Area, and the historic downtown are frequently suggested for visitors. The area also has galleries, museums, and ancient archaeological sites linked to local Indigenous cultures.

  • What are some hiking trails in Hillsborough?

    Hillsborough has scenic routes like the Riverwalk, a paved path along the Eno River, and nearby forested trails in Occoneechee Mountain State Natural Area. These areas invite gentle walks, birdwatching, and quiet nature escapes.

  • What are some family activities we can do in Hillsborough?

    Picnic by the Eno River, enjoy local playgrounds, or participate in children’s story hours at neighborhood libraries. Occasional festivals and craft workshops add to the family experience.

  • What are some of the best day trip ideas from Hillsborough?

    Explore nearby natural spaces with more hiking trails or spend a day discovering the art, music, and historic districts in surrounding towns. Vineyards, museums, and nature preserves around the region expand your options.

  • Are there any pet friendly accommodations available in Hillsborough?

    Many vacation rentals in Hillsborough welcome pets, especially homes and cottages in residential neighborhoods. Pet-friendly parks and walking paths, like the Riverwalk, make it easy to explore with your companion.

  • What are some local tips for visiting Hillsborough?

    Explore Hillsborough’s historic downtown to find public art, locally run shops, and small museums. Locals suggest catching the farmers market for seasonal produce and enjoying walking paths along the water.

  • What is Hillsborough known for?

    Hillsborough is known for its well-preserved historic district, a vibrant local arts scene, and access to riverside parks. The town supports a strong tradition of community events and creative gatherings.

  • What are the best hidden gems to explore in Hillsborough?

    Around Hillsborough, you might discover art studios tucked into side streets, indie bookstores, or less-traveled trails winding through local parks. Heritage sites and small, locally run shops encourage a slower pace of exploration.

  • What are the best foods to try in Hillsborough?

    Hillsborough’s markets and cafes feature Southern-inspired fare, fresh-baked pastries, and locally roasted coffee. Farm-to-table dishes, homemade pies, and classic barbecue reflect the region’s food traditions.

  • What should I bring for a trip to Hillsborough?

    Comfortable walking shoes, layers for weather that shifts between 30–88°F (-1–31°C) seasonally, and rain gear for wetter months are suggested. A reusable water bottle and sun protection help while exploring parks and trails.

  • What is the nightlife in Hillsborough like?

    Hillsborough’s nightlife is cozy, centering on neighborhood pubs, cafes, and occasional live music in local venues. Evenings often feature outdoor dining, craft beverages, and community gatherings.

  • What are the most popular events or festivals in Hillsborough?

    Hillsborough hosts an art walk in the spring, outdoor concerts during summer, and seasonal markets around late fall. The local parade and historical reenactments are also frequently suggested.

  • Are there family friendly vacation rentals in Hillsborough?

    Hillsborough has family-friendly stays, including vacation homes and apartments with kitchens and extra space. Many are located near parks or in quiet residential neighborhoods.

Destinations to explore