Vacation rentals in Hillsborough

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Top-rated vacation rentals in Hillsborough

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Guest favorite

Cabin in Durham

5.0 out of 5 average rating, 267 reviews

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.

Jul 6 – 13

G$27,551 GYD per night

Guest favorite

Guesthouse in Hillsborough

4.95 out of 5 average rating, 223 reviews

The Store in Hobo, a reader/writer’s retreat.

The Store in Hobo: a dog friendly reader/writer’s retreat in a renovated general store. Formerly “Paul’s Grocery” from 1943-73, the Store is on the Bellevue Mill Circle hilltop, an eclectic neighborhood bordering historic downtown Hillsborough. Whether you’re coming alone, with a friend or a small family, this comfy space will inspire creativity and provide serenity. Need room for 2 more? See The Mill House in Hobo on AirBnB. On the same property and with kitchen. (No dogs in Mill House)

Oct 31 – Nov 7

G$28,468 GYD per night

Guest favorite

Apartment in Rougemont

4.96 out of 5 average rating, 164 reviews

Cozy Rougemont Studio w/Walking Trails - Farm Time

Welcome! Our newly renovated Farm Time studio, with full kitchen, is perfect for a quiet get away. Nestled among a lush treeline and picturesque pond, this 1-bathroom apartment with queen bed and full sleeper sofa, is the perfect place to relax. Spend crisp mornings strolling through the green fields or enjoy a fire overlooking the pond at night. There’s also plenty to do in nearby Hillsborough (10 miles) and Durham (18 miles) - museums, parks, markets, and restaurants. RDU Airport (34 miles).

Sep 29 – Oct 6

G$19,762 GYD per night

Guest favorite

Guest suite in Hillsborough

4.94 out of 5 average rating, 104 reviews

Luxurious 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!

Jun 5 – 12

G$23,818 GYD per night

Guest favorite

Guesthouse in Hillsborough

4.97 out of 5 average rating, 194 reviews

CFCB cabin retreat minutes from Duke, NCCU, & UNC

Cozy, wheelchair-accessible, recently renovated cabin with unique decor and a sitting porch, located in a beautiful, mature, piedmont forest that abounds with wildlife and has hiking trails along New Hope Creek. Ideal for a quiet retreat but only 8 minutes from UNC Hospital, Hillsborough Campus and within 15 to 25 minutes from Duke University, University of North Carolina at Chapel Hill, North Carolina Central University and historic downtown Hillsborough. Guests of all walks of life welcome.

Aug 2 – 9

G$27,668 GYD per night

Guest favorite

Apartment in Hillsborough

4.98 out of 5 average rating, 140 reviews

Downtown Hillsborough Luxury Retreat #5

Brand new fully equipped retreat tucked away on a quiet street. Located in the vibrant downtown historic district of Hillsborough. Enjoy the beautiful scenery, architecture, restaurants/ bars and the lively arts and culture scene. From art and river walks to live music as well as farmers markets and festivals. Top of the line appliances, quality mattresses, luxury modal sateen linens, washer/ dryer, grills with propane, front & back balconies and complimentary parking in the rear of building.

Oct 15 – 22

G$36,638 GYD per night

Guest favorite

Cabin in Hillsborough

4.99 out of 5 average rating, 256 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, homemade granola, 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.

Jun 27 – Jul 4

G$29,906 GYD per night

Guest favorite

Guesthouse in Hillsborough

4.96 out of 5 average rating, 333 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.

Aug 11 – 18

G$24,198 GYD per night

Guest favorite

Bungalow in Chapel Hill

4.96 out of 5 average rating, 347 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 chickens, a veggie garden, wood-fired PIZZA OVEN and nearby hiking trails. Our lifestyle embraces beauty and sustainability through permaculture.

Jun 16 – 23

G$25,742 GYD per night

Guest favorite

Tiny home in Chapel Hill

4.93 out of 5 average rating, 610 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

Jun 14 – 21

G$23,420 GYD per night

Guest favorite

Farm stay in Chapel Hill

4.98 out of 5 average rating, 482 reviews

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 with stocked pond -open floor plan of 1000 sq.ft. -fully stocked kitchen -high speed wireless internet with YouTube TV; ESPN -on-site washer and dryer (free) -stairs from ground to apartment -4 vehicles parking; small moving truck too -outdoor grill

Jul 21 – 28

G$28,666 GYD per night

Guest favorite

Cabin in Hillsborough

5.0 out of 5 average rating, 136 reviews

Spacious Poolside Guesthouse on Private Pond

Our 67-acre property, Split Rock, is located 25 min. from Duke University and UNC-Chapel Hill. We are also 15 min. from Carrboro & Hillsborough, a historic, walkable community. Our guesthouse is a large pool cabana with kitchenette & queen bed overlooking a 4.5-acre pond surrounded by uninterrupted woodland. You are welcome to canoe, fish, walk our trails, play disc golf, or just enjoy the peaceful view. Split Rock is ideal for couples and solo travelers.

Jul 26 – Aug 2

G$26,911 GYD per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Hillsborough vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Hillsborough's top sights

Occoneechee Mountain State Natural Area37 locals recommend

Walmart Supercenter4 locals recommend

Wooden Nickel Pub40 locals recommend

Hillsborough BBQ Company20 locals recommend

Food Lion3 locals recommend

El Restaurante Ixtapa4 locals recommend

Other great vacation rentals in Hillsborough

Guest favorite

Guesthouse in Rougemont

4.91 out of 5 average rating, 192 reviews

Cozy Cottage on a Hilltop

Apr 3 – 10

G$17,492 GYD per night

Guest favorite

Guesthouse in Hillsborough

4.98 out of 5 average rating, 52 reviews

Sunlit Cottage Perfect for Two

Jun 17 – 24

G$18,081 GYD per night

Guest favorite

Guest suite in Hillsborough

4.99 out of 5 average rating, 85 reviews

Private suite with kitchenette. Walk to downtown!

Jan 10 – 17

G$27,045 GYD per night

Guest favorite

Guesthouse in Hillsborough

4.93 out of 5 average rating, 43 reviews

Adorable 1 bedroom guest house with free parking!

Jul 18 – 25

G$21,880 GYD per night

Guest favorite

Farm stay in Hillsborough

4.93 out of 5 average rating, 60 reviews

Horse Farm, Cozy 2bdrm Suite, Creek Side Views

Aug 11 – 18

G$28,880 GYD per night

Guest favorite

Farm stay in Hillsborough

5.0 out of 5 average rating, 26 reviews

Eye of the Rooster Farm

Sep 9 – 16

G$33,639 GYD per night

Guest favorite

Tiny home in Hillsborough

5.0 out of 5 average rating, 34 reviews

Peaceful tiny house retreat on 30 acre farm

Jan 6 – 13

G$40,719 GYD per night

Guest favorite

Home in Hillsborough

5.0 out of 5 average rating, 60 reviews

Charming Downtown Hillsborough Cottage

Jan 18 – 25

G$48,108 GYD per night

Show all

Quick stats about vacation rentals in Hillsborough

Total rentals
40 properties
Wifi availability
40 properties include access to wifi
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Pet-friendly rentals
20 properties allow pets
Family-friendly rentals
20 properties are a good fit for families
Total number of reviews
1.9K reviews

Frequently Asked Questions

Do house rentals in Hillsborough have wifi?
Absolutely! We offer over 20 house rentals with wifi in Hillsborough. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Hillsborough have a kitchen?
Absolutely! We offer over 20 house rentals with a kitchen in Hillsborough. Enjoy a tailored experience with all the comforts you desire.
Are there vacation rentals with a dedicated workspace in Hillsborough?
Yes! Work meets play with ease at over 20 vacation rentals in Hillsborough featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do house rentals in Hillsborough have free parking?
Absolutely! We offer over 20 house rentals with free parking in Hillsborough. Enjoy a tailored experience with all the comforts you desire.
Are there pet-friendly vacation rentals in Hillsborough?
Four-legged friends are welcome in Hillsborough. Choose from more than 20 vacation rentals for guests traveling with pets.
What are the most popular amenities for House Rentals in Hillsborough?
Enhance your stay in our House Rentals with the most popular amenities: over 20 homes with wifi, over 20 homes with air conditioning, over 20 homes with a kitchen, over 20 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.
Are there family-friendly vacation rentals in Hillsborough?
Hillsborough has more than 20 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Do house rentals in Hillsborough have air conditioning?
Absolutely! We offer over 20 house rentals with air conditioning in Hillsborough. Enjoy a tailored experience with all the comforts you desire.

Vacation rentals in Hillsborough

Top-rated vacation rentals in Hillsborough

Vacation rentals for every style

Houses

Hotels

Unique stays

Popular amenities for Hillsborough vacation rentals

Stay near Hillsborough's top sights

Other great vacation rentals in Hillsborough

Guesthouse in Rougemont

Guesthouse in Hillsborough

Guest suite in Hillsborough

Guesthouse in Hillsborough

Farm stay in Hillsborough

Farm stay in Hillsborough

Tiny home in Hillsborough

Home in Hillsborough

Quick stats about vacation rentals in Hillsborough

Total rentals

Wifi availability

Rentals with dedicated workspaces

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Frequently Asked Questions

Do house rentals in Hillsborough have wifi?

Do house rentals in Hillsborough have a kitchen?

Are there vacation rentals with a dedicated workspace in Hillsborough?

Do house rentals in Hillsborough have free parking?

Are there pet-friendly vacation rentals in Hillsborough?

What are the most popular amenities for House Rentals in Hillsborough?

Are there family-friendly vacation rentals in Hillsborough?

Do house rentals in Hillsborough have air conditioning?

Destinations to explore