Holiday rentals with a pool in Orange County

Eye of the Rooster Farm

Steve and Angel welcome you to a cozy apartment at our farm surrounded by nature. Less than 5 miles from historic Hillsborough, UNC Hospital Hillsborough campus, and less than 15 miles from Duke/UNC university campuses. Enjoy fresh eggs for breakfast from our chickens and fresh vegetables grown on the property (seasonal). Relax at the pool area. This is a common space shared with the hosts, which are professional, friendly, and mature individuals respectful of others, especially our guests.

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!

Charming Cabin with Private Wooded Pond

The Cabin is situated near our home on 67 woodland acres, 15 min. from Hillsborough and 25 min. from Duke University and UNC-Chapel Hill. The Cabin is a converted horse barn with lofted ceilings, kitchenette, living area, dining table, bathroom, outdoor patio, and bedroom area separated by a partial wall. The pool and swimming pond are a few steps away. You are welcome to canoe, fish, walk our trails, play disc golf, or just enjoy the peaceful views. Ideal for couples and business travelers.

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!

Willow-Updated Chapel Hill Condo w/ Community Pool

**Pool CLOSED 2025 for refurbishing** Your family will be close to everything when you stay at this centrally-located 2 bedroom condo. Enjoy this quiet diverse community with just a walk across the street to Harris Teeter, restaurants, movie theater, and the local farmers market at University Place, & Free transit. 5 minute drive to UNC campus, Dean Dome, Keenan Stadium, and UNC hospitals. With I-40 less than 2 miles away, you will have quick & easy access to Duke University and RTP.

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.

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.

Renovated Modern 2 Bedroom UNC Townhome with Pool

My space is a charming rental in Chapel Hill, tastefully furnished and conveniently located for travelers visiting Chapel Hill or other nearby areas for leisure and work. The 2 bedroom, 1.5 bathroom, two-story rental has all the guest amenities and space you'll need to enjoy your stay in Chapel Hill! You'll love our guest amenities. In addition to free parking, you can enjoy guest essentials and Netflix. Save us to a wishlist!