Holiday rentals with a pool in Hillsborough

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Top-rated rentals with a pool in Hillsborough

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Superhost

Guest suite in Hillsborough

4.96 out of 5 average rating, 157 reviews

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!

Superhost

Guesthouse in Raleigh

4.99 out of 5 average rating, 175 reviews

Modern Retreat near Downtown Raleigh

Come relax in our centrally located modern escape. This second story, 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. Walk to the beautiful Five Points Neighborhood. Less than 10 min ride to downtown, trendy Person Street, NC State campus, and 20 mins to RDU airport

Superhost

Farm stay in Hillsborough

4.9 out of 5 average rating, 109 reviews

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.

Superhost

Farm stay in Hurdle Mills

4.98 out of 5 average rating, 206 reviews

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.

Superhost

Guesthouse in Raleigh

4.95 out of 5 average rating, 360 reviews

Raleigh Oasis Close to it All

The pool is OPEN. Pack a swim suit! Construction Discount in effect (see the Guest Safety section below) An owner-occupied private residence with a large private 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 of the things Raleigh/Durham have to offer.

Superhost

Cottage in Whitsett

5 out of 5 average rating, 175 reviews

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!

Superhost

Apartment in Cary

4.87 out of 5 average rating, 119 reviews

Boho Hideaway in Cary - near RDU & downtown

We accommodate stays for 30 days+! Drop us an inquiry! We are nestled on a tree lined road, just 5 minutes away from downtown Cary! Unwind in the nature filled environment, while still being close enough to get into the city. Walking distance to Greenway trail which is great for a stroll or exercise. 5 minutes to major shopping and eateries. 5 minutes to downtown Cary & 20 minutes to downtown Raleigh, 9 min to airport. Safe and serene. We are dog friendly!

Superhost

Cabin in Hillsborough

5 out of 5 average rating, 165 reviews

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.

Superhost

Guesthouse in Durham

4.99 out of 5 average rating, 194 reviews

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.

Superhost

Condo in Downtown Durham

4.8 out of 5 average rating, 114 reviews

Downtown Durham Midcentury Flat

THE POOL IS OPEN! Tucked in a quaint and historic complex, including gardens, grills, picnic tables, shuffle board, and a beautiful outdoor, saltwater pool. We are also just a few minutes' walk from Duke's East Campus, the South Ellerbee Creek Trail head, and Durham's popular Brightleaf and Central Park Districts. The best coffee, food, beer, and shopping that Durham has to offer is all just a leisurely stroll away.

Superhost

Tiny home in Raleigh

4.97 out of 5 average rating, 259 reviews

Casa Paradiso *An Experience in Living Tiny*

This shipping container turned tiny house is 350 square feet of charm and thoughtful design. Enjoy all of what the city of Raleigh has to offer while still feeling miles away. Located on the back corner of 3/4 of an acre, we have a small stock tank pool and plenty of outdoor space to enjoy. The property is located just a 5-minute drive from the heart of downtown Raleigh. Pool season is Memorial Day - Labor Day

Superhost

Condo in Downtown Durham

4.8 out of 5 average rating, 312 reviews

Downtown "Bull Durham" Condo

We are tucked in a quaint, historic condo community conveniently located near Duke University and Medical Center and all that dynamic downtown Durham has to offer. Walking distance to Central Park, Brightleaf, DPAC, American Tobacco and more. A true oasis within the city, the grounds include grills, sitting areas as well as a sparkling salt water pool.