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Holiday rentals with a pool in Hershey

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Quick stats about holiday rentals with a pool in Hershey

  • Total holiday rentals

    Explore 90 holiday rentals in Hershey

  • Nightly prices starting at

    Hershey holiday rentals start at €78 per night before taxes and fees

  • Verified guest reviews

    Over 790 verified reviews to help you choose

  • Family-friendly holiday rentals

    80 properties offer extra space & child-friendly amenities

  • Rentals with dedicated workspaces

    60 properties have a dedicated workspace

  • Wifi availability

    90 of Hershey holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Hershey rentals

  • 4.8 Average rating

    Hershey stays are highly rated by guests – averaging 4.8 out of 5!

Top-rated rentals with a pool in Hershey

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

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Top guest favourite
A circular pool, measuring 17 feet in diameter, is shown with clear water reflecting the sky. Lush greenery surrounds the area, with trees providing a backdrop. The pool deck features light-colored flooring and a ladder for easy access, creating a serene outdoor space.
Home in Womelsdorf

Whitetail Hill Homestead |POOL|Fire Pit |Family

Welcome to our home! Located in a rural, quiet area, this home is the perfect family friendly getaway! 5 bedrooms and 3 Full bathrooms means plenty of space for everyone! Enjoy a beautiful view overlooking a nearby valley field, watch for wildlife at the edge of the fields, or enjoy a cozy fire in our outdoor fire ring! Indoors enjoy tastefully selected decor, a large modern kitchen, stocked with everything you need, a coffee bar, and comfortable bedrooms! Enjoy our 17' diameter pool this summer

4.97 out of 5 average rating, 118 reviews
Guest favourite
An expansive outdoor pool is set against a backdrop of lush greenery and trees. Warm lighting from the stone cottage bathes the area in a soft glow, creating a tranquil ambiance in the early evening. The pool's water reflects blue hues, inviting a sense of relaxation.
Cottage in Wrightsville

The Stone Cottage w-hot tub, a romantic escape

Experience the ultimate private, romantic retreat tucked away from the hustle and bustle. Our unique hideaway offers over a mile of seclusion from the nearest road, immersing you in nature’s quiet beauty. Relax in the Brand-new Saltwater pool and hear the gentle hums of a train rolling along on the other side of the river. Indulge in the luxurious amenities our property has to offer. Rejuvenate in the hot tub, or warm up by the Breeo Firepit with a Latte from the Breville Espresso Machine.

4.96 out of 5 average rating, 204 reviews
Top guest favourite
The exterior of a welcoming A-frame home is shown, featuring a spacious porch with wooden railings. Two seating areas, including a swing and chairs, are surrounded by greenery and colorful flowers. A flag and hanging plants add a bright touch to the inviting entrance.
Home in Jonestown

Relax in your lower-level living space and enjoy.

Relax with your friends or family at this peaceful / quiet 23 acre Appalachian Vista. As you drive in the quarter mile drive and approch Appalachian Vista Aframe home nestled up against the base of the Appalachian mountain. Feel free to relax by the pool or if your adventurous walks or biking throughout the wooded trails of the Appalachian plus tubing / kayaking the swatara creek or just enjoy nature wildlife from the front porch. Cozy up in our fully furnished with kitchen lower level lodge.

4.95 out of 5 average rating, 214 reviews
Top guest favourite
A serene view captures the home nestled amidst green grass and trees. The pool glistens in the sunlight, surrounded by a spacious patio and seating area. Rolling farmland stretches across the horizon under a soft, cloudy sky.
Villa in Paradise

Hilltop Mansion: Farm Views+HotTub+Pool+GameRoom.

This gorgeous home is located at the very top of a hill in one of the most central locations in Lancaster County. You'll be surrounded by breathtaking views of the nearby farmland and the interior has been beautifully decorated in calming, neutral tones. No amenity has been spared for your stay some of which include a spacious master suite, stunning kitchen, Keurig machine, large game room, a kid's toy room, a firepit, yard games and a patio with outdoor seating, a hot tub, pool and a grill.

4.98 out of 5 average rating, 243 reviews
Guest favourite
A dining area is presented with a farmhouse-style table surrounded by metal chairs. A wooden centerpiece filled with glass vases holds fresh flowers. A stone fireplace is adorned with greenery and decorative items, while a vintage sign adds character to the space.
Bungalow in Lancaster

The River Nook in Lancaster

Our cozy three bedroom, two bathroom riverside cottage comfortably sleeps 6-8 adults, includes a 3 sided fireplace, fully stocked kitchen, and multiple seating areas both indoors and outdoors. Scandinavian, rustic/modern decor includes a hanging rope bed. Outdoor pavilion and spacious backyard in a quiet neighborhood make this the perfect getaway! *5 min to downtown Lancaster *5 min to the Riverdale Manor *10 min to Dutch Wonderland *15 min to Sight & Sound Theater *40 min to Hershey Park

4.96 out of 5 average rating, 623 reviews
Guest favourite
A spacious two-story house is set against a bright blue sky filled with fluffy white clouds. Lush green lawns stretch around the home, featuring neatly manicured grass and a variety of landscaping that enhances the serene rural setting.
Home in Lebanon

Farm Homestead-spacious house on working farm

Experience life in the country on a working farm in Amish country. Waking up to a beautiful sunrise, watching horse & buggies out your front window, open fields with geese out the back are just a few advantages to this beauty in the country. Centrally located between Hershey, Harrisburg, Gettysburg, Lancaster & Mt. Gretna. Plus just a 10 minute drive to Lebanon Expo Center & VA Hospital, 15 minutes off the turnpike, same distance to the PA Renaissance Faire & LVC. Come be our guests!

4.94 out of 5 average rating, 205 reviews
Guest favourite
A spacious backyard features a large in-ground pool with two fountains, surrounded by a concrete deck. Lounge chairs are positioned around the pool, and vibrant flowers add color. A screened gazebo is visible in the background, providing shaded seating for relaxation.
Home in Mechanicsburg

POOL & Lrg Private Yard, Gazebo, Outdoor Kit/Bath!

Hershey, Gettysburg, and the Dutch Country are at your fingertips, yet you'll enter your own private retreat in this comfortable home on a large corner lot with mature trees in a peaceful neighborhood. Newly remodeled kitchen! Conveniently located to all the attractions of Central PA, with Hershey 30 minutes to the east, Gettysburg 30 minutes west, and the Amish Country 45 minutes South. Ski Roundtop is only 9 miles from the house! Easy access to PA Interstates and the PA Turnpike!

4.89 out of 5 average rating, 101 reviews
Top guest favourite
A cozy bedroom features a spacious bed dressed in rich green linens. A dresser with drawers is positioned beside the bed, while three landscape prints adorn the wall. Light beige walls complement the light carpeting, and mirrored closet doors are visible.
Guest house in Elizabethtown

Pondview Paradise w/Heated Pool, near Hershey

Our guest house is a warm, inviting space perfect for one person, a couple, or families. Expect a family friendly neighborhood, while being surrounded by nature. Cozy up by the fireplace and relax by the pond! Enjoy your private deck and shared family pool as well as free guest parking. Perfect location surrounded by Lancaster, Hershey & Harrisburg. Five minutes away from Iron Stone Ranch! A short drive to Hershey Medical Center for families with loved ones staying at the hospital.

5.0 out of 5 average rating, 111 reviews
Guest favourite
Home in Myerstown

Hershey Retreat | Pool, Spa, Sauna, Plunge, & Pond

Come and relax with the family or friends in this spacious and stylish home with special touches: ➤ Mins to Hersheypark and all things Hershey ➤ Pool ➤ Hot Tub ➤ Pond w 2 kayaks ➤ Bass catch & release ➤ EV Charger ➤ Sauna and outdoor shower ➤ BBQ grill for cookouts ➤ Fully equipped kitchen ➤ Air hockey table ➤ Pack n Play ➤ Cold Plunge ➤ Playground ➤ Outdoor firepit Note: The caretaker lives in a separate home onsite; friendly dogs stay with him. You will have full privacy.

4.9 out of 5 average rating, 115 reviews
Top guest favourite
Guest house in Lititz

The Grey Wolf (studio-style loft suite)

Enjoy the clean, comfy, eco-friendly & private loft space with your own private HOT TUB! Situated on top of a hill in the beautiful lake area of Lititz, PA, you will enjoy lovely views and quiet privacy. The main house is detached & adjacent to the loft suite. The loft is located on the top floor of the carriage house. Explore charming downtown Lititz just 4 miles away! Pool open Memorial Day-Labor Day. Hot tub open year round. ONE parking space/EV charging fee

4.95 out of 5 average rating, 372 reviews
Top guest favourite
A charming A-Frame cabin is surrounded by trees, featuring a stone exterior and a spacious deck. Soft lighting illuminates the entryway, while wildlife such as a deer and birds are present nearby. A wooden pathway leads from the cabin into the natural landscape.
Cabin in Goldsboro

Star Gazer Luxury A-Frame Wood Cabin. Near Harrisb

Escape to our charming A-Frame cabin nestled amidst 16 acres of breathtaking woodland, offering an unmatched retreat for nature enthusiasts. Immerse yourself in the awe-inspiring vistas, relish the cozy interiors, unwind in the indulgent hot tub, and gather around the inviting fire pit. Discover unparalleled comfort, tranquility, and natural beauty that will leave you rejuvenated. Don't miss out on this extraordinary experience; secure your reservation now!

5.0 out of 5 average rating, 107 reviews
Top guest favourite
The inground pool is framed by lounge chairs and shaded seating areas. A welcome sign is displayed near the pool, with a clear blue sky and greenery visible in the background, showcasing a serene outdoor space perfect for relaxation.
Villa in Leacock-Leola-Bareville

Beautiful split level home,with pool and hottub

Welcome to Anne’s house! A spacious,newly renovated,split level home in Lancaster county. Minutes from the main attractions such as Dutch wonderland,the town of Intercourse,Bird in Hand and much more. You will have the house,beautiful inground pool,hottub and backyard all to yourself. Anne’s house comes with designated work space,WiFi,three smart TVs plus ,and all your basic needs

4.99 out of 5 average rating, 191 reviews

Popular amenities for Hershey rentals with a pool

KitchenWifiPoolFree parking on premisesAir conditioning

House rentals with a pool

Top guest favourite
Home in Manaheim

92 Acre Beautiful Farmhouse with in-ground pool

4.98 out of 5 average rating, 120 reviews
Guest favourite
A spacious living area features a large sectional sofa adorned with decorative pillows. A foosball table stands to the side, while an elegant chandelier provides soft lighting. Natural light enhances the inviting entrance, which leads to a dining area visible through an archway.
Home in Millerstown

3000sq Parisian MidCentury WFH & Family RiverHaven

4.94 out of 5 average rating, 140 reviews
Guest favourite
A country-style kitchen features mint green cabinetry and a wooden countertop. Stainless steel appliances include a microwave, oven, and dishwasher. A deep farmhouse sink is positioned beneath a window adorned with light curtains, while a bowl of fruit and kitchen essentials are displayed on the counter.
Home in Strasburg

Findley Farm View Cottage (Outdoor Pool!)

4.94 out of 5 average rating, 159 reviews
Guest favourite
A welcoming pathway lined with vibrant flowers leads to a charming building. Flanking the path are evergreen trees and neatly arranged garden beds. A wooden structure can be seen in the distance, surrounded by lush greenery, creating a serene outdoor setting.
Home in Gap

White Horse Guest Home w/ Pool & Spa

4.88 out of 5 average rating, 101 reviews
Guest favourite
A well-maintained lawn surrounds a sparkling pool, complemented by palm trees and vibrant flower planters. The property features a multi-level home with a charming deck, providing a serene backdrop of lush greenery under a bright sky.
Home in West Hanover

Wonderful Amenities 15 Mins To Hershey Attractions

4.92 out of 5 average rating, 96 reviews
Top guest favourite
An outdoor pool features a shimmering blue surface, surrounded by a white picket fence. A basketball hoop stands at one end, with potted plants adding a touch of greenery nearby. The sky glows with soft pastel hues as the sun sets in the background.
Home in Annville

Sweet Adventure! Large Pool

5.0 out of 5 average rating, 18 reviews
Guest favourite
Home in Palmyra

Modern Pool-Side Paradise

4.95 out of 5 average rating, 65 reviews
Top guest favourite
The historic brick house is set against a vibrant sunset, with a pool in the foreground. Lounge chairs are positioned near the poolside, and an umbrella provides shade at a nearby table. Lush greenery surrounds the space, adding to the inviting atmosphere.
Home in Campbelltown

The Stauffer House

4.95 out of 5 average rating, 73 reviews

Apartment rentals with a pool

Superhost
The exterior of the resort is showcased, featuring a multi-story building with a red roof. Surrounding green lawns and trees create a natural setting, while distant rolling hills can be seen in the background, providing a sense of openness.
Apartment in Hershey

Smell the Chocolate from Hershey Park 2BD Condo

5.0 out of 5 average rating, 3 reviews
Guest favourite
An inviting inground pool is surrounded by a spacious stone patio and lush greenery. Several lounge chairs, shaded by umbrellas, are positioned along the edge. Guests are enjoying the water while others are gathered nearby, creating a lively and relaxed atmosphere.
Apartment in Ephrata

The Highland Oasis

4.93 out of 5 average rating, 45 reviews
Guest favourite
A well-lit outdoor pool area is framed by a charming gazebo featuring a set of black chairs and a table. The swimming pool displays a gentle curvature, complemented by lounge chairs positioned nearby. A multi-story building is visible in the background, contributing to the resort atmosphere.
Apartment in Hershey

The Suites at Hershey- 2 bdrm sleeps 8

5.0 out of 5 average rating, 11 reviews
Superhost
The exterior of the resort is presented, featuring a multi-story building with a red roof and multiple balconies. The surrounding green landscape and gentle hills create a serene backdrop, while a clear sky enhances the vibrant setting.
Apartment in Hershey

Hershey 2BR Resort Villa nearby Hershey Park

5.0 out of 5 average rating, 5 reviews
Superhost
A scenic view of a theme park is showcased, featuring a wooden roller coaster and vibrant amusement rides against a backdrop of lush greenery and distant hills. Colorful flowers in the foreground provide a touch of natural beauty to the landscape.
Apartment in Hershey

Hershey, PA- Hershey Resort-2Bd Suite - BG

Guest favourite
The entrance to Suites At Hershey is framed by well-maintained landscaping, featuring neatly shaped bushes and vibrant flowers. The sign above reads 'Clubhouse & Registration,' indicating the welcoming atmosphere of the property. Bright blue skies and fluffy clouds enhance the inviting appearance.
Apartment in Hershey

2 Bedrooms, 2 Bath Suites at Hershey Resort Lux

5.0 out of 5 average rating, 8 reviews
Superhost
The hotel building features a modern design with multiple stories and a red roof. Surrounding greenery provides a serene environment, while balconies offer outdoor access. The property is set against a backdrop of gently rolling hills under a clear blue sky.
Apartment in Hershey

Hershey 2BR Suite Villa nearby Park w/indoor pool

Other holiday rentals with a pool

Top guest favourite
A welcoming living area features a green sofa adorned with colorful cushions and an orange ottoman. A plush area rug with intricate patterns lies underfoot. A fireplace sits against a decorative wall, complemented by holiday greenery. Natural light fills the space through nearby windows.
Townhouse in Reinholds

Gasthof Fretz -your Bavarian hideaway!

4.95 out of 5 average rating, 228 reviews
Guest favourite
An open concept living area is presented, featuring a comfortable brown sofa with cushions and a decorative throw. A coffee table with slender legs is placed in front. A dining table with four chairs and large windows allows natural light, enhancing the space's cozy feel.
Holiday home in Lancaster

Sweet Retreat

4.95 out of 5 average rating, 213 reviews
Superhost
Tiny home in New Holland

Waterfront A-Frame Studio at Red Run #116

4.96 out of 5 average rating, 118 reviews
Top guest favourite
A view of the exterior of a black barn-style building, surrounded by rising grass and landscaping. The yard features a gentle slope adorned with gravel and boulders, complemented by vibrant autumn foliage in the background.
Guest suite in Mohnton

Loft 311

5.0 out of 5 average rating, 204 reviews
Superhost
The image displays a large swimming pool set within a well-maintained outdoor area. Sun loungers surround the deck, and greenery serves as a backdrop, adding to the serene atmosphere. The clear blue water reflects the sky, creating a refreshing appearance.
Cottage in Lancaster

Summer Splendor Cottage with Private Pool

4.97 out of 5 average rating, 188 reviews
Top guest favourite
Home in Dauphin

River View Lodge

4.97 out of 5 average rating, 36 reviews
Top guest favourite
Home in Myerstown

The Fern Cottage [hot tub + pool]

5.0 out of 5 average rating, 62 reviews
Guest favourite
Home in Auburn

Pool | Hot Tub | 3 Min to Lake | Pets Allowed

5.0 out of 5 average rating, 22 reviews

Destinations to explore