Holiday rentals with a pool in Hershey

Find and book unique homes with a pool on Airbnb

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
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
4.95 out of 5 average rating, 177 reviews

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.

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
4.97 out of 5 average rating, 191 reviews

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.

Guest favourite
The image displays a mountain cabin and a separate pool house, both surrounded by lush greenery. A large swimming pool with gently curving edges reflects warm outdoor lighting from the structures. Comfortable seating areas with chairs can be seen around the pool, inviting relaxation.
Cabin in Reinholds
4.88 out of 5 average rating, 105 reviews

Mountain Top Cabin w/ Hot Tub + Private Pool!

BNB Breeze Presents: Mountain Top Cabin! Embark on a journey with your loved ones to this expertly crafted mountain retreat in the breathtaking landscape of Lancaster County, PA. Brace yourself for an unforgettable vacation, where exploration of nearby natural wonders, thrilling escapades at Hershey Park, and relaxation by the pool and hot tub await! ✔ Hot Tub ✔ Private Pool + Pool House (Seasonal) ✔ Multiple Living Areas + Sunroom ✔ Fully-Equipped Spacious Kitchen ✔ Smart TV's ✔ Log Cabin

Top 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
4.96 out of 5 average rating, 590 reviews

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

Top 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
4.94 out of 5 average rating, 196 reviews

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!

Top guest favourite
Guest house in Lititz
4.94 out of 5 average rating, 324 reviews

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

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 Leola
4.99 out of 5 average rating, 148 reviews

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 ,a chairlift for the main stair case,and all your basic needs

Guest favourite
The exterior of the property showcases a well-maintained, single-story home surrounded by lush green grass and light landscaping. A large tree stands prominently in the front yard, with two chairs positioned on a small patio area, inviting relaxation in a peaceful setting.
Home in Conestoga
4.9 out of 5 average rating, 206 reviews

3-bedroom house in quiet area bordering park

This beautiful property in Conestoga, PA borders Silver Mine Park which has a creek, soccer and baseball fields, and hiking trails. Located 10-15 minutes from Lancaster City, ~20 minutes from many popular (Amish-related) tourist attractions, ~10 minutes from the Pequea boat launch, and ~18 minutes from the Pinnacle Overlook this is the perfect property either for an action-packed vacation or a peaceful, relaxing one.

Top guest favourite
Home in Annville
4.99 out of 5 average rating, 157 reviews

Holidays Near Hershey w/ Hot Tub & Arcade!

🎅 Ho, Ho Ho...Tis The Season 🎅 Funky Dutchman Will Be Decorated For The Holidays From December Through January! Roll Those Skeeballs, Crank The Jukebox and Battle It Out With Aliens On Our Galaga Arcade! Prefer To Grill Some Steaks, Take a Dip In Our BRAND NEW Hot Tub, Summer Stock Tank Pool or Roast S'mores By Our Firepit? We Have Ya Covered! We Even Have A Small Movie Theater Room!

Top guest favourite
A spacious sleeping area features a large bed with decorative blankets and a nautical-themed wall art above. Soft lighting from bedside lamps enhances the comfortable atmosphere. A seating area with a sofa and a dresser is visible in the background, creating a seamless blend of relaxation spaces.
Flat in Elizabethtown
4.94 out of 5 average rating, 166 reviews

Splash by Hershey

Come and relax by the pool just on the outskirts of Hershey. Enjoy this newly remodeled studio apartment with private entry that is also handicapped accessible. Large private bath, queen sized bed, and small kitchenette. You can look out the large picture window which overlooks the wooded area behind, watch birds, deer, and other wild life.

Top guest favourite
The spacious living area features a cozy seating arrangement with a wooden bench and upholstered ottomans. A large television rests above the decorative fireplace, while artwork adorns the walls. A game table and an area rug add to the inviting atmosphere, complemented by natural light from the windows.
Home in Lebanon
4.99 out of 5 average rating, 315 reviews

Holidays Near Hershey w/ Hot Tub & Firepit!

🎅 Ho, Ho Ho...Tis The Season 🎅 Red Door Retreat Will Be Decorated For The Holidays From December Through January! Trust In The Reviews! A Truly Unique "Red Door Retreat" Nestled In a Family-Oriented Neighborhood Just 13 Miles and 20-30 Minutes From Hershey's Chocolate Factory and Amusement Park.

Top 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
4.95 out of 5 average rating, 153 reviews

-The Pool Cottage at The Roundtop Estate-

Want a Unique Getaway? New Salt Water Pool Hot Tub/Firepit Espresso Machine! Where to start? From the beautiful lap pool, to the architecture, to the luxury furnishings, to the woods surrounding it, to the hot tub, breeo firepit with a cooking rack to the Gas burning fireplace, An oasis!

Popular amenities for Hershey rentals with a pool

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 $117 SGD per night before taxes and fees

  • Verified guest reviews

    Over 430 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

  • 4.9 Average rating

    Hershey stays are highly rated by guests – averaging 4.9 out of 5!