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.

0 of 0 items showing

1 of 3 pages

Guest favorite

Home in Manheim

4.98 out of 5 average rating, 102 reviews

92 Acre Beautiful Farmhouse with in-ground pool

The 1st floor includes a custom cherry kitchen w/ island, 2 dining rooms to ensure plenty of space for meals, games or various activities, spacious family room, living room, full bathroom, half bath, and a grand 4 season sun room overlooking peaceful pastures. After a busy day site seeing beautiful Lancaster County, enjoying Hershey Park or touring the Amish country, come back & relax by the newly renovated in ground pool with space for sunning & a gazebo with table for hanging out in the shade.

Guest favorite

Guesthouse in Jonestown

4.97 out of 5 average rating, 134 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

Home in Annville

4.98 out of 5 average rating, 120 reviews

WOWZA! Hot Tub, Firepit, Gameroom Near Hershey!

✨ Trust In Our Reviews! ✨ We're a Local Family Who Pride Ourselves In Offering Quality Accommodations, Extra Amenities and Unmatched Hospitality Only 15 Minutes To Hershey Attractions! ✨ 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, Summer Stock Tank Pool or Roast S'mores By Our Firepit? We Have Ya Covered! We Even Have A Small Movie Theater Room!

Guest favorite

Villa in Morgantown

5 out of 5 average rating, 102 reviews

Mill Road Farmhouse: Restored with Beautiful Pool.

The Mill Road Farmhouse is a destination in and of itself. Immaculately restored inside and out, this home is a true retreat in the middle of Amish Country. We have a feeling you will be spending all of your time relaxing by pool and hot tub during the warmer months (or maybe grilling up a feast in the brand new outdoor kitchen area) and curled up next to one of the four indoor fireplaces during the winter months. And then of course end each day star-gazing while sitting around the campfire.

Guest favorite

Bungalow in Lancaster

4.96 out of 5 average rating, 541 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, 115 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

4.92 out of 5 average rating, 167 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

4.95 out of 5 average rating, 177 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 Honey Brook

4.94 out of 5 average rating, 249 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.

Guest favorite

Rental unit in Lancaster

4.83 out of 5 average rating, 170 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.

Guest favorite

Home in Lebanon

4.99 out of 5 average rating, 269 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

4.91 out of 5 average rating, 175 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.