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.

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.

Gorgeous Mid-Century Home with Pool

This newly styled mid-century gem in Chapel Hill will wow you! Our spacious 4-bedroom home boasts a private pool, vaulted ceilings, and lush wooded views. With multiple living areas and luxurious amenities like a steam shower, it's the perfect private retreat for families and groups. Experience architectural beauty and modern comfort just minutes from UNC and local trails, comfortably accommodating your entire group. **Please Note: You must be 25+ years old to book this property.**

Forest Garden Suite - Private studio in the trees!

Lovely townhouse studio in the woods convenient to UNC-Chapel Hill (bus stop is across the street) as well as Durham and RTP (by car). You will be surrounded by greenery in this established neighborhood minutes from Umstead Park and Bolin Creek. Feel free to contact us during your stay for anything you may need including info on our town's numerous top-rated restaurants and fun outdoor activities. We hope you enjoy your stay with us! 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.

The Durham II • Vibe 8725

Discover The Durham II, a 2-bedroom, 2-bathroom walk-up on the second floor in Durham, NC. This pet-friendly unit includes a kitchen, Wi-Fi, air conditioning, and access to a gym and pool, making it perfect for up to four guests. Durham's thriving food scene, American Tobacco Campus, and Research Triangle energy make this city a hidden culinary gem, while craft breweries and Duke University proximity create a dynamic atmosphere.

The Banana House | A Quirky Carrboro Gatewaway

The Banana House 🍌 is a colorful, creative Airbnb in downtown Carrboro, NC, just minutes from Chapel Hill. From the outside, it’s modest. Inside, it’s bold, bright, and full of personality — with a pink banana-themed kitchen, playful living space, and a cozy bedroom made for slow mornings and sleep-ins. If you’re looking for a unique Carrboro Airbnb that’s walkable, memorable, and anything but boring, you’ve found it.