Vacation rentals with a pool in Hershey

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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 favorite
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, 180 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 favorite
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, 201 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.

Top guest favorite
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, 597 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 favorite
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, 197 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!

Guest favorite
A welcoming living room features two gray armchairs with yellow accent pillows, positioned around a modern white coffee table. A large wall-mounted TV is surrounded by soft lighting, and a small indoor plant adds a touch of greenery to the space.
Apartment in Lancaster
4.83 out of 5 average rating, 175 reviews

Posh Apartment/ Off Street Parking/10 Mins To City

You will have private parking steps away from the private entrance to the apartment. This apartment includes a dining room area, with additional seating at the breakfast nook, washer, dryer, 55” SmartTV; everything you need to feel at home! The balcony has seating and a small table. You can access our backyard that features a bonfire area, a large pool lined with comfortable lounge chairs, and an outdoor dining area with TV, speakers, and grills. Hosts live next to the property.

Top guest favorite
Guesthouse in Lititz
4.94 out of 5 average rating, 333 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 favorite
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, 154 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 favorite
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, 210 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 favorite
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
4.95 out of 5 average rating, 152 reviews

Findley Farm View Cottage (Outdoor Pool!)

Designed to be a quaint farmhouse getaway set in the middle of Amish country. Close to Sight and Sound Theater! Very easy to get to and close to many amenities, attractions, and destinations. This home, since its construction, has been a family gathering place. The doors have always been open to guests, and we want to continue that tradition and welcome you!

Top guest favorite
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.
Apartment in Elizabethtown
4.94 out of 5 average rating, 167 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 favorite
Cottage in Wrightsville
4.96 out of 5 average rating, 164 reviews

-The Pool Cottage at The Roundtop Estate-

Want a Unique, Romantic, winter Getaway? Twinkling Christmas tree Hot Tub/Firepit Espresso Machine! Where to start? From the beautiful setting, 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!

Top guest favorite
A spacious farmhouse is set among lush greenery and trees, partially shrouded in morning fog. A welcoming porch is visible, hinting at cozy seating areas beneath the overhang. The expansive lawn provides a serene setting, enhancing the tranquil atmosphere of the property.
Farm stay in New Ringgold
4.9 out of 5 average rating, 200 reviews

Four bedroom Farmhouse with Pool

Your stay features a four bedroom 1800s farmhouse that sits back off of a quiet country road with a view. Meet Mimm's Wishing Well rescue cats; go for a walk with our silly goats, Hilly and Billy at the barn. Hug a Valais Blacknose sheep, pet a pet chicken, find an egg. Relax.

Popular amenities for Hershey rentals with a pool

Quick stats about vacation rentals with a pool in Hershey

  • Total vacation rentals

    Explore 90 vacation rentals in Hershey

  • Nightly prices starting at

    Hershey vacation rentals start at € 77 per night before taxes and fees

  • Verified guest reviews

    Over 430 verified reviews to help you choose

  • Family-friendly vacation rentals

    80 properties offer extra space & kid-friendly amenities

  • Rentals with dedicated workspaces

    60 properties have a dedicated workspace

  • Wi-Fi availability

    90 of Hershey vacation rentals include wi-fi 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!