Holiday rentals with a pool in Chapel Hill

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!

Location · Value · TV

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.

Location · Family · Pool

Relaxing Saltwater Pool Oasis and Modern Retreat

Come relax in our centrally located modern escape. This garage top apartment is drenched in natural light & includes all the extras. The open floor plan living, dining, and kitchen is perfect for couples, friends, and business travelers looking for upscale accommodations. Our salt water lounge pool is open to guests June-Oct. NEW traditional sauna is open year-round. Walk to the beautiful Five Points Neighborhood. 10 mins by car to downtown or NC State campus, and 20 mins to RDU airport

Value · Family · Access

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.

Family · Location · View

LUXE Home 4 Mins Duke/DPAC | King Beds, BBQ, Pool

Make unforgettable memories in this spacious, beautifully designed home for you + 9 guests! Perfect for family gatherings, sporting events, & special occasions. Located in heart of Downtown Durham, just 4 mins from Duke, Bulls stadium, DPAC, & Tobacco Trail. Cozy up around the fire pit, enjoy a BBQ, or relax w/fresh popcorn & vinyl records. Retire in luxurious beds + sheets & head to the gourmet coffee bar in the AM. Free access to nearby gym w/pool. 4 air mattresses and EV charger avail.

Location · Family · Breakfast

Spacious 3bd Lake & pool near Duke UNC Southpoint

Our home is a very comfortable and spacious 3 bedroom -2.5 bath perfect for families. The bedroom are spacious each with own TV. It has a full kitchen , laundry closet with washer and dryer. Outdoor deck area with outside sitting & bbq facilities upon request .Living room for the family gather .Our location: steps from wonderful walk around the lake.and community pool for the summer travelers Conviniently located near Duke urgent care- Southpoint , Duke , UNC & Tabacco trail.

Value · Family · Nearby

Raleigh Oasis Close to it All

The pool is OPEN and ready for the 2026 season! Don't forget to pack a swimsuit. An owner-occupied private residence with a large private saltwater pool and guesthouse above the detached garage. Enjoy the sights and sounds of a stocked koi pond or observe nature from the private balcony. Minutes from Rex Hospital, Crabtree Mall, Art Museum and PNC arena. The location cannot be beat! Feel far from the city while close to all the things Raleigh/Durham have to offer.

Value · Location · Getting around

Where Relaxation Meets Home/POOL/KING suite/RTP

Experience the best of the Triangle from our stylish and conveniently located townhome. Perfect for families and business travelers, our sanctuary offers easy access to Research Triangle Park, RDU Airport, and the prestigious universities of Duke, NC State, and UNC. Within minutes, you can explore beautiful parks, browse local shops, and savor delicious meals at nearby restaurants. We've created a space we love, and we can't wait to welcome you home for the holidays!

Value · Family · Decor

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.

Location · Value · Breakfast

Chic Poolside Hideaway Near Duke & UNC

Tucked away in the back of our 1927 property sits The Sidekick, a thoughtfully restored carriage house surrounded by peaceful woods & grand homes. Part cowboy clubhouse, part restful retreat, The Sidekick is a conveniently-located getaway for couples, solo travelers, or small groups. Take a dip in the saline pool, lounge in the mature garden, or just rest your sleepy head on luxurious linens in your sweet lil' loft bedroom.

Value · Location · Indoor spaces

100 Year-Old Historic Brick 2BR Loft |Large Patio2

Party Policy: To ensure a great experience for everyone, parties are not allowed. Violations of house rules such as excessive noise, smoking, or additional unapproved guests will result in a $300 fee, reservation cancellation, and removal from the property. If that works for you, please send an inquiry or instant book — we’d love to host you! Booking Requirement: Guests must have at least 3 reviews on their profile.

Value · Location · Outdoor spaces

Garden Oasis in the heart of downtown Durham

Beautifully renovated must stay if visiting Durham downtown. Within walking distance of many restaurants and city sites. Close to Duke Medical and Campus, and a stone's throw from many of the great restaurants and activities downtown has to offer. Pearl mill (122) offers a secret garden courtyard, an oasis of serenity amongst the action of the city. Huge pool to enjoy, March through October, weather permitting.

Family · Value · Bathroom