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.

Quiet convenience near UNC/Duke

Updated with cathedral ceiling and fireplace in living room. Open plan. Bright breakfast area in well appointed kitchen. First floor bedrooms. Main bedroom has King sized bed and walk in closet. Dual vanities, soaking tub and separate shower. Second bedroom has queen sized bed and window bench seat. Washer dryer in hallway. Wood floors throughout. Loft overlooking the living room. Community pool and tennis courts. Walk or bike to shopping, greenway, trails. Easy access to I-40, UNC, Duke

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.

Charming Modern Townhouse

Discover our 2BR townhome, 8 mins from Chapel Hill. Ideal for families or work stays, it accommodates 5 guests. Enjoy amenities smoke-free environment, free parking, trail access, and a seasonal pool. In the vibrant Winmore neighborhood, offers easy access to the Chapel Hill bus line. Additional features: Smart TV, fast WiFi, standing desk, master bedroom with ensuite, guest room, sleeper couch, and laundry closet. Book your stay for a modern yet tranquil experience.

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.

Cozy 2-bed, 2.5 bath near UNC

The townhome is nestled in a cul-de-sac neighborhood and is part of a larger townhome complex that has access to a clubhouse, pool, tennis court, basketball hoop, and doggy play area. The property provides direct access to the Bolin Creek trail for walking, running, and biking. The townhome is a short, 0.3 mile walk to the town/university bus stop and a 10-minute drive to UNC Hospital.