Holiday rentals with a pool in Hillsborough

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.

*NEW SAUNA - Modern Retreat with Relaxing Pool

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

Convenient to Duke Hosp/Univ & Walkable to DT

1st floor condo with its own HVAC system, Pearl Mills is in walking distance to DT, arts and culture, parks, and restaurants/entertainment venues. There are great outdoor spaces, comfy beds, and a charming, unique building. The 1st-floor condo is next to the pool, gardens, cookout areas, shuffleboard, and large chessboard. Close to Duke East Campus and Duke Hospital. Well-suited to couples, solo travelers, and business travelers. Small dog <25 pounds allowed for $87/stay. Pool opens 5/2/26.

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.

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.

Countryside Getaway UniqueDomeA/serenefarm retreat

Welcome to our serene countryside farm glamping dome, nestled in the heart of nature on a sprawling 28-acre property. Perfect for a peaceful getaway, our dome offers a unique blend of comfort and adventure.Escape the hustle and bustle of city life and relax under the stars. Whether you're looking for a romantic getaway, a family vacation, or a solo retreat, our property offers the perfect setting for a memorable experience. Discover the beauty and tranquility of countryside living.

The Garden Cottage

The Garden Cottage is centrally located in the Piedmont area of NC, being only 5 miles from Elon University, within 5 miles to most of Burlington area shopping and restaurants, 1.5 miles to I-85/40, 15 miles to Greensboro, 28 miles to High Point and 37 miles to Chapel Hill. The Cottage has just recently been renovated and equipped with all the conveniences of home. Enjoy your time visiting and exploring the areas around our location. Hope to see you soon!

Downtown Durham Midcentury Flat

Two-person limit includes children. Thank you! (The complex is very strict about this policy.) Tucked in a quaint and historic complex, including gardens, grills, picnic tables, shuffle board, and a beautiful outdoor, saltwater pool. Walking distance to Duke's East Campus, the South Ellerbee Creek Trail head, and Brightleaf and Central Park Districts, including the best coffee, food, beer, and shopping that Durham has to offer!

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.

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.

Condo @ Historic Duke Tower

1 King bedroom (+sleeper sofa) condo at historic Duke Tower in downtown Durham. By the pool and the large courtyard with all kinds of plants, a pool, picnic areas. WIFI, cable, & utilities are included. Relaxing with shopping and restaurants nearby. Duke Tower has a strict 2 person per condo policy. (And yes, they do count children of any age.)