Holiday rentals with a pool in Orange County

Winmore Townhome | Central, Spacious, Comfort

Enjoy this bright, open-concept end-unit in Chapel Hill’s walkable Winmore community. Perfectly located just 10 mins from downtown Chapel Hill, Carrboro, and UNC campus. Walk to Bolin Creek trails, the neighborhood pool, or playgrounds. Ideal for families, remote work, or events in Chapel Hill. Features an open concept living, kitchen, and dining area, all fully equipped for a comfortable stay. Upstairs features two large bedrooms each with its own bathroom. Loft equipped with standing desk.

Stylish Carrboro Townhome | Walk to UNC | Patio

Modern, freshly updated 2BR / 1.5BA townhome in the heart of Carrboro, just a short walk to UNC, Franklin Street, Weaver Street Market, restaurants and coffee shops. Bright, art-filled interiors with fully equipped quartz kitchen, cozy electric fireplace, 65” Roku TV, fast Wi-Fi, multiple workstations, family-friendly amenities, air purifiers and seasonal-only community pool access. Enjoy a private patio, in-unit laundry, and free parking in a peaceful residential community close to everything!

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.

Amazing Retreat: 55 Acres of Nature + Pool + Pond

AMAZING 4100sf GUEST RETREAT ON 55 ACRE PARK-LIKE FARM Come enjoy the self-contained 4100sf 6BR 6-1/2 bath guest retreat located only 20 to 25 minutes to Duke & UNC. Your guest retreat is in our Luxurious Custom Home with beautiful views of nature. Large saltwater Pool, hot tub, fire pit, trail & acres of pastures to roam. High end furnishings with contemporary flair. Designer's personal home & no expense spared to create a one-of-a-kind oasis for folks to enjoy. NO PARTIES OR EVENTS.

Willow-Updated Chapel Hill Condo w/ Community Pool

**Pool CLOSED 2025/2026for 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.

Stylish Chapel Hill Condo

Beautifully decorated condo in a quiet, well treed, and sunlit setting. Light and bright south facing. This condo is the top condo of a 3 condo grouping, so no one is above you and there is only one unit beside. Private and quiet. Two bedroom, one with new bunkbeds. Each bedroom has its own private 4 piece bath. Centrally located and on the bus line for easy access to universities and schools. Grocery stores, coffee shop and restaurants within walking distance.

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.

UNC Cottage- near Univ/Hospital, YMCA, Franklin St

This beautifully decorated 2 bed/1 bath home is a treasure. Our kitchen is fully stocked and ready for gourmet cooking. The cottage sleeps 4 people. Each bedroom has high speed wifi and a desk. The living room is perfect for reading books or watching movies on our Smart TV. The renovated bathroom has stunning tile floors and a tile shower/tub. Enjoy our large deck. See if you can spot our family of 6 deer who call our woods home.

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.