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

Guesthouse in Lititz

4.94 out of 5 average rating, 267 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

Guesthouse in Jonestown

4.99 out of 5 average rating, 125 reviews

Appalachian Vista relax and enjoy nature.

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.

Guest favorite

Place to stay in Harrisburg

4.92 out of 5 average rating, 125 reviews

The Villa- 2 BR Combo + Living areas + Pool Access

Kick back and relax in this calm, stylish space. Great location, close to the city and riverfront. Enjoy the outside patio, watch the wildlife stroll by. Shared access to pool, hot tub and fire pit is available (coordination with owners required- guidebook contains instructions). There is convenient off-street parking and the rooms have a separate outside entry. Gas fireplace in the living room adds a romantic flair. Everything you need for a lovely weekend, week or month is just inside!

Guest favorite

Bungalow in Lancaster

4.96 out of 5 average rating, 529 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

Guest suite in Mohnton

4.99 out of 5 average rating, 106 reviews

Loft 311

Enjoy a peaceful vacation tucked away in a valley below a swath of Lancaster County farmland. Located in Adamstown, PA, "Antiques Capital USA", this studio-style loft is less than 5 minutes from 272, 222, and the PA Turnpike, and less than half an hour from the many tourist attractions and local hotspots in Lancaster and Reading. If you enjoy bicycle riding, you'll be able to travel on your own steam to a dozen local antique shops, or take it easy and lounge by the pool with the family.

Guest favorite

Home in Myerstown

4.91 out of 5 average rating, 154 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

Home in Lebanon

4.96 out of 5 average rating, 175 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

Home in Annville

4.98 out of 5 average rating, 111 reviews

WOWZA! Hot Tub, Cowboy Pool, Firepit Near Hershey

✨ Trust In Our Reviews! ✨ We're a Local Family Who Pride Ourselves In Offering Quality Accommodations, More Amenities and Unmatched Hospitality In The Hershey Area! ✨ Welcome to "The Funky Dutchman" ✨ 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, Stock Tank Pool or Roast S'mores By Our Firepit? We Have Ya Covered!

Guest favorite

Home in Lebanon

4.98 out of 5 average rating, 258 reviews

Hot Tub {staycation} Vibes Near Hershey

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!

Guest favorite

Home in Conestoga

4.92 out of 5 average rating, 169 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.

Guest favorite

Home in Strasburg

4.94 out of 5 average rating, 131 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!

Guest favorite

Rental unit in Elizabethtown

4.95 out of 5 average rating, 132 reviews

Splash by Hershey

Come and relax by the pool just on the outskirts of Hershey. Enjoy this newly remodeled studio appartment with private entry that is also handicapped accessable. 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.