Vacation 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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Guest favorite

A sparkling pool reflects the clear blue sky, surrounded by lounge chairs with vibrant orange cushions. The nearby house features a wooden facade with large windows and a chimney, while a shaded seating area is housed in a gazebo, offering an inviting outdoor space.

Guesthouse in Lititz

4.94 out of 5 average rating, 314 reviews

The Grey Wolf (studio-style loft suite)

Enjoy my clean, comfy, eco-friendly & private loft space! We are situated on top of a hill in the beautiful lake area of Lititz, PA, known as Speedwell Forge. You will enjoy lovely views and quiet privacy from the property. The main house is adjacent to the loft suite. The loft is the top floor of the carriage house. Explore charming downtown Lititz only 4 miles away! Pool season: Memorial Day-Labor Day. (Exact dates TBD) **ONE parking space only** Overnight EV charging on site for a small fee.

Guest favorite

An inviting swimming pool is surrounded by lush greenery, featuring a smooth slide for added fun. The clear blue water reflects the sky, and the pool area is paved with concrete, providing a spacious layout for relaxation and enjoyment.

Home in Jonestown

4.96 out of 5 average rating, 164 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 charming house is seen surrounded by lush greenery, with a circular above-ground pool enclosed by a wooden deck. The inviting outdoor area features a spacious lawn, and the porch is adorned with seating for relaxation and socializing.

Home in Auburn

5 out of 5 average rating, 107 reviews

11-Acre Farmhouse Retreat | Creek, Pool, Hot Tub

✨ Peaceful Creekside Farmstead Getaway! Located on 11 acres of serene land, this farmhouse offers a perfect mix of relaxation and adventure and is an entire farmhouse offering private, peaceful accommodations! ★ Private Outdoor Pool ★ Game Room with Pool Table & Ping-Pong ★ 52" Smart TV for entertainment ★ Free Wi-Fi ★ Fire Pit & Blackstone Griddle ★ 7-Person, 93-Jet Hot Tub for relaxation ★ Creekside Views with a bridge in front of the house ★ Spacious Outdoor Area perfect for kids to play!

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, 177 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 private swimming pool is set against a backdrop of lush greenery, enclosed by a black fence. The water appears clear and inviting, with steps leading into the shallow end. Surrounding trees provide shade, creating a peaceful outdoor space.

Bungalow in Lancaster

4.96 out of 5 average rating, 584 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 favorite

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

4.91 out of 5 average rating, 216 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.

Guest favorite

An above-ground swimming pool is situated in a spacious grass area, surrounded by greenery. A deck extends from the back of the house, with lounge chairs positioned nearby. The sky displays a soft, cloudy hue, hinting at an evening ambiance.

Home in Lebanon

4.94 out of 5 average rating, 193 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 favorite

An aerial view captures the contemporary home set against a lush wooded landscape, featuring a heated saltwater pool surrounded by a fenced area. The gentle slope leads down to the Susquehanna River, with hills in the background illuminated by the setting sun.

Home in Harrisburg

4.99 out of 5 average rating, 108 reviews

Mountain Retreat * Heated Pool * Amazing Views!

★ Heated Saltwater Pool ★ Open May - September! Welcome to Mountain View Retreat! This beautiful contemporary home is situated high on a wooded hillside and offers great privacy. Lots of large windows and sliding glass doors with AMAZING VIEWS of the Susquehanna River and the City of Harrisburg! This WHEELCHAIR ACCESSIBLE home is perfect for families and friends. With over 5,000 sq feet of living space and a large 53 ft long deck with a panoramic view that really is quite magical!!

Top guest favorite

An outdoor space features a circular stock tank pool, surrounded by natural stone and arranged decorative fencing. String lights hang above, casting a soft glow, while lush greenery lines the background, creating a serene atmosphere.

Home in Lebanon

4.99 out of 5 average rating, 310 reviews

Foosball, Hot Tub & Firepit + Stock Tank Pool

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. Jam Packed w/ Amenities & Newly Designed In 2024! Red Door Features an Arcade 1Up Infinity Table w/ 50+ Games, Pac Man Arcade, Popcorn & Gumball Machine, Fully-Fenced Yard (w/ Grass!), 45 Jet Hot Tub, Stock Tank Pool, Foosball, Firepit & Grill!

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, 140 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

A tree house glows softly at night, adorned with twinkling lights. A wooden pathway leads to the entrance, bordered by green foliage. The structure features large windows that reflect the surrounding ambiance, while fairy lights create a whimsical appeal in the trees above.

Treehouse in Mount Joy

4.97 out of 5 average rating, 121 reviews

Lothlorien Tree House

*PLEASE READ OUR FULL LISTING DETAILS BEFORE BOOKING YOUR STAY, no linens or pillows provided* This tree house glamping retreat is for the adventurous at heart...and for Lord of the Rings lovers wanting to experience a little bit of Middle Earth here on our Earth. Head to YouTube and check out our video tour of the tree house and grounds- just search for “Lothlorien Tree House” and it will be the video by Gretchen R.

Superhost

A round above-ground pool is surrounded by a grassy area, with steps leading up to a wooden deck. A lounge float is placed on the water's surface, while a charcoal grill and pool equipment are positioned nearby, framed by lush green trees in the background.

Home in Conestoga

4.9 out of 5 average rating, 199 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.