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.

Upscale 1 bedroom 1 bath stylish living dinning

This unique place has a style of its own. Its a brand new carriage home 950 sq ft of living space, for a main home. The apartment is located above the detached garage, All hardwood floors, Stylish kitchen, DW, wine cooler, stove, refrigerator, W/D, separate entrance. large smart tv. Fully furnished with kitchen equipments, utensils, linen etc. One block away is a community pool and a gym. Garage parking is optional. The entrance to the apartment is independent and is inside not an outside

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!

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 6Ba guest retreat space in our 7000sf home located only 20 to 25 minutes to Duke & UNC. Luxurious Custom Home with endless views of nature. Huge private Saltwater Pool, hot tub & fire pit for guests, 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 space for guests to enjoy. NO PARTIES/EVENTS.

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.

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.

Forest Garden Suite - Private studio near UNC

Lovely townhouse studio in the woods convenient to UNC-Chapel Hill as well as Durham and RTP. You will be surrounded by greenery in this established neighborhood a short walk away from Umstead Park and Bolin Creek. With a private entrance, free parking, and a convenient bus stop across the street, it's the perfect home base whether you're visiting family, touring campus, attending a game, or exploring the Triangle. Chapel Hill Zoning Compliance Permit STR-23-9

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.