Holiday rentals with a pool in Chapel Hill

5 out of 5 average rating, 126 reviews

A wooden sign welcomes visitors to Two Dachshund Farm, featuring the farm's name in bold green and orange lettering. Decorative silhouettes of dachshunds are displayed on either side. Surrounding the sign is a patch of green grass and flowering plants, enhancing the inviting atmosphere.

Farm stay in Franklinton

Two Dachshund Farm (Lavender & Fiber Farm), LLC

We are a working fiber/lavender farm convenient to Raleigh, Louisburg, Wake Forest, Henderson, & Durham. Meet our alpacas, sheep, llamas, Angora goats & more. Tours are included for our guests ifAdditional visitors will need to pay a tour fee. Use of the pool is for registered guests only. Events will be considered. The unit is a 700 sq ft apartment over a garage with private entrance. Twenty stairs lead up to the apartment. A pullout couch accommodates 2 younger children or a teenager/adult.

Guest suite in Hillsborough

A spacious guest suite features a queen bed with soft white linens, surrounded by elegant wooden furniture. A cozy seating area with two upholstered chairs sits near a decorative fireplace. Light wood floors and built-in shelves create a warm atmosphere, complemented by natural light from large windows.

4.96 out of 5 average rating, 165 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!

4.99 out of 5 average rating, 184 reviews

A modern living area features a bright blue sofa and a matching accent chair. A wooden coffee table sits centrally, with a decorative bowl. A wall of shelves showcases various decor items. Natural light fills the space through large windows, framed by greenery outside.

Guesthouse in Raleigh

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

Farm stay in Hillsborough

Three horses of varying colors are seen standing near a wooden fence in a spacious pasture. A covered shelter is located in the background, while a clear blue sky with scattered clouds accentuates the serene landscape.

4.91 out of 5 average rating, 118 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.

4.98 out of 5 average rating, 129 reviews

A sparkling blue swimming pool is surrounded by a spacious deck, featuring several lounge chairs for relaxation. A wooden fence provides privacy, while lush trees line the background under a clear sky.

Guesthouse in Durham

Gordon Guesthouse Studio Suite w/ hot tub & pool!

Book now & enjoy the pool, balcony & luxury high-end hot tub. Open 24hrs, exclusively for all guests to use. We welcome you to our little piece of paradise, not far from downtown Durham & Raleigh close to RDU. We offer a well-appointed studio, meticulously cleaned, with a queen Tempurpedic mattress, premium linens, fireplace, full kitchen, washer/dryer, 2 smart TV's & high speed wifi. *Please be aware* Due to allergies & health risks, we are unable to accommodate any animals. Sorry :-(

4.96 out of 5 average rating, 384 reviews

Guesthouse in Raleigh

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.

5 out of 5 average rating, 104 reviews

A modern living area features two stylish green sofas facing a contemporary electric fireplace, with a large flat-screen TV mounted above. Natural light floods the space through two windows, while a sleek coffee table holds a decorative bowl and chess set.

Home in Durham

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.

4.96 out of 5 average rating, 166 reviews

A vibrant living space features an orange sectional sofa adorned with soft cushions. Colorful plants and artwork add character, while natural light filters through sheer curtains. A decorative mirror reflects the lively atmosphere, and a hexagonal pattern rug lays on the floor, enhancing the eclectic decor.

Condo in Carrboro

The Banana House

Prepare for an incredible surprise when you pull up to a modest exterior block apartments. Once you enter the space, you’ll be bombarded with color, a pink banana themed kitchen and a monochromatic bedroom perfect for sleep-ins. It’s a bit of a Barbie Dream House escape set in downtown Carrboro. The location is walkable and VERY close to the farmers market, Carrmill Mall, Mercato, Orange County Social Club and many more restaurants and bars. Please note…the art and plants shown do change

4.93 out of 5 average rating, 116 reviews

A modern living room features a comfortable gray sofa adorned with blue accent pillows. A round coffee table sits in front, situated on a patterned area rug. A ceiling fan and large window provide natural light, while the open layout leads to the dining area and kitchen.

Apartment in Raleigh

Upscale Living 5 Min From Downtown

Unwind in this stylish luxury corporate one-bedroom apt. Near Hospitals and Downtown Raleigh. Full of top restaurants, movie theater, spas, shops, historic landmarks, and attractions. Adventure through Raleigh and the region easily from this prime location. Relax indoors amongst designer furnishings, flat-screen TV, and luxe amenities. ✔ Fully Equipped Kitchen ✔ Comfortable Bedroom w/ Queen Bed ✔ Open Concept Living Area ✔ Office Desk ✔ High-Speed Wi-Fi ✔ Free Parking Learn more below!

5 out of 5 average rating, 165 reviews

The living area features a spacious sectional sofa accompanied by cozy armchairs. A coffee table sits on a patterned rug, with art pieces adorning the walls. A Smart HDTV is positioned on a decorative console, and natural light enters through high ceilings.

Townhouse in Cary

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!

Guesthouse in Hope Valley

A serene backyard is framed by lush greenery and features a pristine saline pool with bench seating. Several deck chairs are arranged under large umbrellas, and the nearby wooden fencing adds a sense of privacy.

4.99 out of 5 average rating, 196 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.

4.79 out of 5 average rating, 133 reviews

A modern living area features a bright orange sectional sofa complemented by a round coffee table. A television is mounted on the wall opposite the seating. Natural light enters through large windows adorned with green curtains, enhancing the space filled with indoor plants and framed art.

Condo in Trinity Park

Downtown Durham Midcentury Flat

**Smoke damage has been fully and professionally remediated as of October 1st, 2025.** 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!

Popular amenities for Chapel Hill rentals with a pool

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.98 out of 5 average rating, 63 reviews

A welcoming living area features a comfortable sectional sofa and two armchairs, arranged on a light area rug. A wooden coffee table occupies the center, adorned with decorative elements. Natural light filters through nearby windows, enhancing the open and airy layout.

Home in Durham

1 story Ranch in South Durham/RTP/UNC/Duke/ RDU

4.85 out of 5 average rating, 34 reviews

A cozy living area features a large sectional sofa upholstered in light fabric, paired with an armchair. A coffee table sits centrally, and an array of framed photographs decorates the walls. Natural light enters through a window, enhancing the neutral color scheme.

Home in North Hills

Entire 2 BR Home in Midtown

4.84 out of 5 average rating, 19 reviews

A charming bungalow exterior features a welcoming front porch adorned with turquoise chairs. The landscaped yard includes a grassy area framed by wooden steps, inviting relaxation. The structure showcases a light-colored facade paired with a gray roof, surrounded by greenery under a clear blue sky.

Home in East Durham

Adorable Bungalow, Minutes from Downtown Durham

5 out of 5 average rating, 19 reviews

An inviting dining area is featured with a round wooden table surrounded by modern black chairs. A large window offers views of the outdoors, while a cozy seating area with a light-colored couch can be seen in the background, complemented by art and warm lighting.

Home in North Ridge

Perfect Retreat-Elegant Comfort & Family Friendly

4.9 out of 5 average rating, 119 reviews

A modern living area features a large wall-mounted TV displaying a serene landscape with mountains and greenery during sunrise. A neutral-toned sofa and decorative elements, including a vase and wooden bowl, complement the space. Stairs lead to an upper level, enhancing the home's spacious feel.

Home in Raleigh

Designer home close to RDU and downtown, sleeps 12

4.74 out of 5 average rating, 38 reviews

A spacious two-story home features a brick façade and a charming front porch. Lush greenery surrounds the entrance, with manicured shrubs and plants enhancing the outdoor appeal. A driveway provides convenient access, leading to a two-car garage.

Home in Hope Valley

Stunning 5 bedroom/3 bath home in Hope Valley Farm

4.96 out of 5 average rating, 49 reviews

An open concept living area features a cozy brown sofa adorned with a textured throw. A large entertainment unit is set against a light wall, while a wooden beam adds character above. The kitchen area, equipped with modern appliances, can be seen in the background.

Home in Cary

Movie Loft Stunner @ Carpenter Village | Walkable

Home in Research Triangle Park

The single-story home features a combination of stone and siding exteriors. A welcoming front porch is highlighted by a blue front door, and white shutters frame the windows. The surrounding yard is maintained with green shrubs and a concrete driveway leading to a garage.

4.95 out of 5 average rating, 39 reviews

Home away from home in Durham with Private Pool!

Condo rentals with a pool

4.98 out of 5 average rating, 58 reviews

A tranquil lake reflects a colorful sunrise, with soft hues of pink and orange merging into a blue sky. Surrounding trees and nearby buildings create a serene backdrop, inviting peaceful moments by the water.

Condo in Cary

Amazing Lake Views! Enjoy the sunrise & wildlife.

Condo in Downtown Raleigh

4.91 out of 5 average rating, 195 reviews

A short walk with a breeze .

4.85 out of 5 average rating, 62 reviews

Condo in Trinity Park

FLAT 127 Downtown Durham

4.96 out of 5 average rating, 110 reviews

A serene view of a calm lake reflects blue skies with scattered clouds. Lush greenery surrounds the water, creating a peaceful natural environment. The scene is framed by nearby trees and well-kept grassy areas, enhancing the tranquil setting.

Condo in Cary

Lake view condo w/office, walk to food/greenway

Condo in Warehouse District

A cozy living area features a blue sectional sofa, accented by decorative pillows. A wooden coffee table sits centrally on a colorful rug. Two lamps provide warm lighting, while an artwork depicting cattle complements the warm-toned wall. A TV is positioned on a black stand.

4.81 out of 5 average rating, 322 reviews

Downtown "Bull Durham" Condo

4.98 out of 5 average rating, 40 reviews

A furnished patio area features two vibrant chairs adorned with floral cushions, set against a backdrop of a sunset. A small, textured stool sits nearby, and decorative lighting adds a warm touch to the atmosphere.

Condo in Morrisville

RTP Condo Near RDU Airport + Pool & Amenities

Condo in Warehouse District

A wooden coat rack stands in the corner next to a black dresser. Natural light from large windows illuminates the space, revealing green walls and warm-toned lamps. Outside, soft evening light highlights a view of the community courtyard.

4.54 out of 5 average rating, 28 reviews

Condo in Downtown Durham - 253

5 out of 5 average rating, 16 reviews

A comfortable living area features a patterned sofa with red accent cushions, a light-colored ottoman, and a single chair. A large window dressed with lace curtains allows natural light to fill the space, alongside a floor lamp and an indoor plant for added decor.

Condo in Carrboro

Bright, clean, nicely appointed 1-bedroom condo

Other holiday rentals with a pool

4.99 out of 5 average rating, 74 reviews

A wooden planter is filled with colorful flowers, including purple and yellow blooms, positioned near a black fence. In the background, a brown horse grazes in a lush green pasture, while a sign reading 'Summer Meadows' can be seen on the fence.

Farm stay in Youngsville

The Cottage at Summer Meadows

4.71 out of 5 average rating, 34 reviews

A comfortable living area is showcased with a gray sofa and two accent lamps on side tables. A dark coffee table serves as a focal point, complemented by decorative items. A plush area rug lies beneath, and built-in shelves are visible in the background.

Home in Woodcroft

Lux King SuiteCentral to Duke, UNC & RDU Airport

4.83 out of 5 average rating, 18 reviews

A bright studio space features a spacious bed adorned with various throw pillows. A kitchenette area is visible in the background along with modern appliances. Decorative touches include wall wreaths and stylish baskets, contributing to a cozy and organized environment.

Guesthouse in Cary

RakShack Studio

Apartment in Research Triangle Park

The entrance of the condo building is presented with a modern design featuring large glass doors. Lush green shrubs flank the entrance, while a neatly maintained lawn adds to the appeal. The building's brick facade is complemented by stylish overhead lighting.

5 out of 5 average rating, 22 reviews

City Loft|King bed | Next to RTP| Home4Holidays

Farm stay in Hillsborough

A large white adirondack chair is positioned on a grassy area, facing a picturesque view of the farm. A white fence delineates the property against a backdrop of lush greenery and a partly cloudy sky, creating a serene outdoor ambiance.

5 out of 5 average rating, 64 reviews

Eye of the Rooster Farm

5 out of 5 average rating, 64 reviews

A well-lit hallway features neutral gray walls and dark wood flooring. White paneling lines the lower section of the walls, complemented by a decorative runner. Double doors on either side lead to additional spaces, while a front door provides natural light and outdoor views.

Townhouse in Morrisville

Where Relaxation Meets Home/KING suite/RTP/POOL

5 out of 5 average rating, 16 reviews

A well-appointed bedroom features a spacious bed with striped linens, flanked by two lamps on dark nightstands. A distinctive light fixture hangs above, while three windows provide natural light, framed by white blinds that allow for privacy.

Townhouse in Durham

Palazzo Di Amore - NEW Luxury Living w/Heated Pool