
Holiday 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.

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.

3000sq Parisian MidCentury WFH & Family RiverHaven
Be lord or lady of your charmingly Instagrammable "French" historic home away from home in the heart of Central PA! Step back in time to the perfect spacious & character filled, completely updated vintage home to explore, work, play & gather in! Sightsee here-Juniata County's Amish Country. Swim at the pool just 2 min. away; bring your boat & tackle, tubes & kayaks-easily access the Juniata River! Gather & relax or take a fast, traffic-free scenic river highway to State College, Hershey & more!

-The Pool Cottage at The Roundtop Estate-
Experience the ultimate private, romantic retreat tucked away from the hustle and bustle. Our unique hideaway offers over a mile of seclusion from the nearest road, immersing you in nature’s quiet beauty. Relax in the Brand-new Saltwater pool and hear the gentle hums of a train rolling along on the other side of the river. Indulge in the luxurious amenities our property has to offer. Rejuvenate in the hot tub, or warm up by the Breeo Firepit with a Latte from the Breville Espresso Machine.

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.

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.

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.

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

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!

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

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

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.

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.
Popular amenities for Hershey rentals with a pool
House rentals with a pool

Findley Farm View Cottage (Outdoor Pool!)

Modern Pool-Side Paradise

Peaceful Retreat Pool and great outdoor space

King’s place, hot tub. Pool is closed until Spring

Isaac Bahney Homestead w/ POOL & HOT TUB

Family Fun Retreat | Pool, Hot Tub & Game Room

Country Land Guest House

Special Hershey getaway, pool, privacy, relax
Condo rentals with a pool

Smell the Chocolate from Hershey Park 2BD Condo

The Suites at Hershey- 2 bdrm sleeps 8

Hershey, PA- Hershey Resort-2Bd Suite - BG

The Highland Oasis

2 Bedrooms, 2 Bath Suites at Hershey Resort Lux

Hershey 2BR Resort Villa nearby Hershey Park
Other holiday rentals with a pool

Blissful Mountain Getaway - Manor on 46 acres

Relaxing Swatara River Front Retreat

Modern Farmhouse: Pool, Hot Tub & Pickleball

Lancaster Retreat-Hot tub, River & Farm Views

Idyllic estate, close to downtown and the Amish.

628 Suite Spot Oasis near Hershey

Family Escape w/ Pool & Play Area Near Hershey, PA

Pool, Hot Tub, Ski Round Top, Firepit, Game Room
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 $87 AUD per night before taxes and fees

Verified guest reviews
Over 550 verified reviews to help you choose

Family-friendly holiday rentals
80 properties offer extra space and kid-friendly amenities

Rentals with dedicated workspaces
60 properties have a dedicated workspace

Wi-Fi availability
90 of Hershey holiday 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!
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- Rentals with a fireplace Hershey
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- Rentals with pools Dauphin County
- Rentals with pools Pennsylvania
- Rentals with pools United States
- Hersheypark
- Dutch Wonderland
- Roundtop Mountain Resort
- French Creek State Park
- Codorus State Park
- Hershey's Chocolate World
- Spooky Nook Sports
- Shady Maple Smorgasbord
- Pennsylvania Farm Show Complex & Expo Center
- Sight & Sound Theatres
- Amish Village
- Lancaster County Convention Center
- Messiah University
- Maple Grove Raceway
- Franklin & Marshall College
- Giant Center
- Broad Street Market
- Lititz Springs Park
- Middle Creek Wildlife Management Area
- Central Market Art Co
- Fulton Theatre
- Rausch Creek Off-Road Park
- National Civil War Museum
- Hawk Mountain Sanctuary




