Holiday rentals with a pool in Hillsborough

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Top-rated rentals with a pool in Hillsborough

Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

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Top Guest favourite

Guest suite in Hillsborough

4.96 out of 5 average rating, 163 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!

Top Guest favourite

Guesthouse in Raleigh

4.99 out of 5 average rating, 181 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

Guest favourite

Farm stay in Hillsborough

4.9 out of 5 average rating, 115 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.

Top Guest favourite

Guesthouse in Raleigh

4.95 out of 5 average rating, 375 reviews

Raleigh Oasis Close to it All

The pool is CLOSED and will reopen May 1st. 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.

Condo in Warehouse District

4.89 out of 5 average rating, 327 reviews

Stylish Flat in DT Durham-Sep A/C-downtown walkabl

This cozy, comfortable downtown poolside condo is located near so much in DT Durham. It is walkable to major attractions, parks, restaurants, and entertainment venues. There are lovely outdoor spaces, comfy beds, and a charming, unique building. The first-floor condo is next to pool, lovely gardens, cookout areas, shuffleboard, and human-sized chessboard. Close to Duke East Campus and Duke Hospital. Business travelers welcome. Non-shedding dogs under 25lbs $75.00. Pool closes 10/31/25.

Guest favourite

Home in Durham

5 out of 5 average rating, 102 reviews

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.

Top Guest favourite

Townhouse in Cary

5 out of 5 average rating, 164 reviews

The Cloverleaf | 1K 1Q 1T | Near DT Cary & RDU

The Cloverleaf is the ideal home away from home for families, friends and business travelers. Spacious, comfortable, and convenient location, central to Raleigh, Durham, Chapel Hill and minutes from DT Cary or RDU. Updated finishes and professional styling in a private setting with access to nearby greenways trails, parks and lakes, plus community pool. Enjoy the large deck overlooking woods, work on high speed internet, watch YouTube TV and cook your own meals. Book your 5 Star Stay!

Guest favourite

Farm stay in Hurdle Mills

4.98 out of 5 average rating, 208 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

Condo in Trinity Park

4.78 out of 5 average rating, 127 reviews

Downtown Durham Midcentury Flat

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! **A note about a smoke smell. There was a fire in the building and we had some smoke damage, but as of October, 2025, the issue has been resolved.**

Top Guest favourite

Cottage in Whitsett

5 out of 5 average rating, 177 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!

Guest favourite

Apartment in Cary

4.88 out of 5 average rating, 121 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!

Top Guest favourite

Cabin in Hillsborough

5 out of 5 average rating, 167 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.