Holiday 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 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, 192 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 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

Guest favourite
An outdoor pool area is surrounded by a spacious concrete deck. Lounge chairs are placed nearby, and a gazebo is visible in the background. The pool's clear water reflects the blue sky, offering an inviting space for relaxation.
Home in Myerstown
4.9 out of 5 average rating, 225 reviews

Charlies 3 bedroom home, pool, hot tub & game room

A 3 bedroom home With in-ground pool that’s open from May 1st-Sept 30th each year. Eco Spa 4 person hot tub that’s available year round & outdoor patio space to enjoy! The house features a full kitchen, 75 inch Smart TV, with Netflix, Comcast Sports. 1 king, 1 queen, & 2 full size beds. Game room including basketball shooting game, air hockey & foosball plus table games. We are conveniently located approximately 30 minutes from Hershey Pa. 30 minutes from Lititz Pa and many restaurants.

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!

Guest favourite
A modern living area is characterized by exposed wooden beams and a cozy fireplace. Two spacious sofas are positioned around a central coffee table, with natural light streaming in through large windows. Artwork adorns the walls, adding a touch of personality to the space.
Home in Honey Brook
4.93 out of 5 average rating, 289 reviews

Ode to the '70's - hot tub & pool in Honey Brook

4 bedroom/2 bath home - modern renovation with retro flair. Large backyard with saltwater pool, hot tub, grill, fire pit, and kids playhouse! (Pool open May-Sept) We've furnished this home with our favorite pieces to create a space that inspires creativity & life. Pickleball courts within walking distance in local park. Paddles and balls provided. Close to the Honey Brook Thrift Store, September Farms & other local attractions! 1/2 hour to Lancaster City, Exton/King of Prussia.

Top guest favourite
Guest house in Lititz
4.94 out of 5 average rating, 326 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, 149 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, 158 reviews

Hot Tub, Arcade, Firepit & Yard Near Hershey!

🎅 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, 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 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.

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 € 78 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!