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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Guest favourite

Bungalow in Lancaster

4.96 out of 5 average rating, 504 reviews

The River Nook

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! *3 min to nearest grocery store *5 min to downtown Lancaster *10 min to Dutch Wonderland *15 min to Sight & Sound Theater *40 min to Hershey Park

2–9 Dec

$242 SGD per night

Guest favourite

Guest house in Lititz

4.95 out of 5 average rating, 241 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.

18–25 Oct

$203 SGD per night

Guest favourite

Guest house in Jonestown

4.99 out of 5 average rating, 101 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.

28 Oct – 4 Nov

$256 SGD per night

Guest favourite

Home in Myerstown

4.91 out of 5 average rating, 125 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.

25 Dec – 1 Jan

$233 SGD per night

Guest favourite

Home in Lebanon

4.96 out of 5 average rating, 163 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!

28 Dec – 4 Jan

$570 SGD per night

Guest favourite

Home in Honey Brook

4.93 out of 5 average rating, 216 reviews

Ode to the '70's private home with Hot Tub!

4 bedroom / 2 bath home - modern renovation with retro flair. Large backyard with grill, campfire pit & swimming pool & newly added hot tub! (Saltwater Pool is open May-September & closed Oct-April - hot tub is open all year) We've furnished this home with our favorite vintage & modern pieces to create a space that inspire creativity & life. Close to the Honey Brook Thrift Store, September Farms & other local attractions! 1/2 hour to Lancaster City, Exton/King of Prussia.

21–28 Sep

$543 SGD per night

Guest favourite

Farm stay in Mount Joy

4.97 out of 5 average rating, 232 reviews

Historic Farm Suite-2 min to Spooky Nook!

Enjoy this cozy 2nd floor guest suite for 2 in a 200 year old farmhouse! The space is a 3 room guest suite, with private entrance, full bath, bedroom and living room. This listing is NOT for the entire house. Our family and dog lives in the main part of the house. Enjoy petting our goats and watching our chickens. An abundance of various birds, deer, and foxes roam the farm and surrounding area. Spend the evening by the fire pit so you can appreciate the quiet & stars.

4–11 Sep

$133 SGD per night

Guest favourite

Home in Lebanon

4.98 out of 5 average rating, 240 reviews

Woo-Wee! {Staycation Vibes} Near Hershey {Hot Tub}

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!

18–25 Dec

$540 SGD per night

Guest favourite

Farm stay in New Ringgold

4.91 out of 5 average rating, 166 reviews

Six bedroom Farmhouse with Pool

Mimm's Country Inn and Stables is a six bedroom farm house with an indoor pool. At the barn we have Valais blacknose sheep, two Nigerian dwarf goats, Americana chickens, Indian Runner ducks, rescue cats and kittens. Stop by our farmstand for chicken eggs in shades of green, peach and beige. Pick your favorite color and build six or a dozen. Hike. Grill. Picnic. Swim. Fish. Play. Read. Sleep. Stay. See you there!

23–30 Apr

$304 SGD per night

Guest favourite

Home in Conestoga

4.92 out of 5 average rating, 145 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.

25 Oct – 1 Nov

$250 SGD per night

Guest favourite

Home in Gettysburg

5.0 out of 5 average rating, 197 reviews

Civil War Farm House w/Heated (seasonal) Pool

Welcome to this historical Civil War Farm House. This stone home built in 1861 by Christian Shriver and was actively used as a field hospital during the war. Mrs Shriver prepared General Reynolds his breakfast on the first day of the battle (which he was killed). The Durboraw's moved here in the early 1890's and have remained here on the farm ever since.

5–12 Mar

$357 SGD per night

Guest favourite

Home in Strasburg

4.93 out of 5 average rating, 116 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!

16–23 Nov

$281 SGD per night