Holiday rentals with a pool in Orange County

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!

Serenity Cottage

Experience the magical beauty and tranquility of Firefly Farm, a 26-acre flower farm nestled in the lush countryside near the historic town of Hillsborough, North Carolina. Immerse yourself in farm life. Stroll our paths and visit our farm animals. Take part in our seasonal delights: flowers bloom April to September, fireflies glitter at dusk during Summer while birds and butterflies delight during the day and Fall brings crisp air as the leaves change (as well as Witch Hazel's haunted barn)!

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.

Lg Pool House w/ Hot Tub Central to RTP*Pool Open*

Discover luxury in this AAA five-bedroom Durham home near Duke Hospital and Duke University. Perfect for family reunions, corporate stays, or small weddings, it features spacious living areas with tasteful decor, a fully-equipped kitchen, and a dining room for memorable meals. Outside, enjoy a private pool (open for the season) and hot tub (open year round) for relaxation. Explore nearby attractions like Duke Gardens and the vibrant Durham arts scene. Ideal for creating lasting memories!

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.

North Carolina Charm

Perfect location, spacious, one story with all the amenities to make your stay comfortable. Less than 15 min away from UNC Chapel Hill with close and easy access to free Chapel Hill buses! Groceries, dining & shopping less than 10 min away. RDU airport 20 min away. Whether you’re looking for a game weekend with 6 other friends, a short walk to visit loved ones at Carol Woods or a place to call home for an extended work trip, North Carolina Charm is what you’re looking for. STR-23-56

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.

Midcentury Home w/King suites near Duke/Downtown

Relax with the whole family at this beautiful midcentury home. This split-level home can accommodate all your needs with 4 bedrooms and 2.5 baths. Enjoy a fully stocked kitchen with granite countertops. Sleep well on multiple King sized beds. Relax in the furnished sunroom. Large backyard with swing set. Go for walks in this safe and quiet neighborhood. Located between I-40 and downtown making it easy to access all the city has to offer.

Quiet home near Lake & Outlets

Quiet 4 bedroom home in Mebane, NC. Whether you're visiting on business or pleasure this home is a great escape. This home boosts walking trails to nearby Lake Michael. Cozy indoor fireplace to unwind after a long day. 5 minute drive to Tanger Outlets, quick commute to UNC, Duke, Elon, UNC Greensboro only 35 minute drive to RDU. Seasonal Pool and Gym access. Complete with everything you need to make your stay worry free.