Holiday rentals in Orange County

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.

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

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!

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.

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.

The Chapel Hill Forest House

Book this incredible tiny house for the perfect romantic getaway in the heart of Chapel Hill! It sits in a private forest full of wildlife but is only a 5-minute walk to Franklin Street and the UNC campus. Enjoy amazing views from the floor-to-ceiling windows of foxes and deer playing on the lawn. Lounge on the wall-to-wall hammock as you gaze at the trees through the skylights. Unwind with a movie in bed played on our massive projector. There's nothing like this anywhere in the Triangle!

Blackwood Mt Bungalow In the Woods with Sauna

Escape to a peaceful hillside retreat nestled in the woods, where the melodies of farm animals and wild birds create a soothing soundtrack. 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 (+$40) and wander through lush flower and vegetable gardens. While close to town, this getaway promises a restorative escape immersed in nature’s serenity and thoughtful living.

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

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.

Bright spacious 2 BR, 8 min to UNC Chapel Hill

Clean and bright, spacious basement apartment in quiet, safe family neighborhood. Fast Wi-Fi at 600+ Mbps. Includes 2 bedrooms with a queen bed in each (plus a rollaway twin size cot), kitchen, living room, game room with ping pong, full bath, laundry, screened porch and private entrance. Spotless and lovingly maintained. Important: No oversized construction / work vehicles. Also, smoking is not permitted in or around the property. (Please see additional important note below!)

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.

The Japandi Dome

Experience a taste of Japandi in this dome home on our small homestead, and enjoy the mind and body benefits of being closer to nature with the comforts of indoor amenities. This unique space is built with a full skylight to allow you to sleep under the night sky. Complete with heating and A/C for year-round comfort, a full zen-inspired bathroom, and luxury European bedding. Enjoy your meal around a Japanese inspired floor table with straw mats and meditation cushion for seating.