Middletown Vacation Rentals

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Aug 5 - Aug 6
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This weekend
Aug 8 - Aug 10
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Aug 15 - Aug 17

Vacation Rentals in Middletown

*Newly* Renovated Stay at modern 3BR Townhome (15 minutes from Harris-Hershey)
Enjoy cooking in this well-equipped kitchen with a dishwasher, toaster, and sink.

*Newly* Renovated Stay at modern 3BR Townhome (15 minutes from Harris-Hershey)

8.8 out of 10, Excellent, (9)
"Everything was very nice at our stay here.Beds were comfortable, plenty of pillows, extra blankets.Kitchen was very clean, new, and it was stocked with dish and cups for cooking and drinking. The wifi was fast and easy to access. I would stay here again for our next Christmas break to visit family.Thank you for being an awesome host!"
*Newly* Renovated Stay at modern 3BR Townhome (15 minutes from Harris-Hershey)
Forest Tree Log Cabin - middletown/Harrisburg/Hershey/Lancaster/York
Cozy cabin-style bedroom with two single beds, wooden dresser, and skylight offering a forest view.

Forest Tree Log Cabin - middletown/Harrisburg/Hershey/Lancaster/York

9.0 out of 10, Wonderful, (2)
"Very clean!"
The price is ￥74,195
￥158,435 total
includes taxes & fees
Aug 11 - Aug 12
Forest Tree Log Cabin - middletown/Harrisburg/Hershey/Lancaster/York
stayAPT Suites Harrisburg-Hershey
Relax in style with a comfortable sofa and armchairs surrounding a cozy fire pit.

stayAPT Suites Harrisburg-Hershey

3.5 star property
8.6 out of 10, Excellent, (122)
"The place was great! Quiet, clean, easy access to parking, central cooling, spacious, beautiful outside seating area."
The price is ￥16,014
￥17,776 total
includes taxes & fees
Sep 2 - Sep 3
stayAPT Suites Harrisburg-Hershey
Iconic "Haines Shoe House" - Hot Tub & Firepit - Featured On HGTV
Relax in a serene outdoor setting with a hot tub, complete with amenities and a cozy patio.

Iconic "Haines Shoe House" - Hot Tub & Firepit - Featured On HGTV

10.0 out of 10, Exceptional, (119)
"Loved our Shoe House stay! The house is adorable. The décor is super cute and comfortable. And the hosts have thought of everything to make your stay enjoyable. A fun, whimsical, and memorable experience for all ages. Many thanks!"
The price is ￥30,407
￥71,242 total
includes taxes & fees
Aug 21 - Aug 22
Iconic "Haines Shoe House" - Hot Tub & Firepit - Featured On HGTV
The Suites at Hershey
Relax by the serene pool surrounded by a charming gazebo and a historic building.

The Suites at Hershey

3.0 star property
9.2 out of 10, Wonderful, (261)
"Beautiful hotel, very comfortable. The staff was friendly. "
The Suites at Hershey
2-bedroom 2nd Floor apartment in Mount Joy with off street parking
Cozy retreat with a single bed and a door to the right, featuring a ceiling fan and light fixture.

2-bedroom 2nd Floor apartment in Mount Joy with off street parking

2.0 star property
9.6 out of 10, Exceptional, (17)
"Highly recommended!"
The price is ￥13,113
￥21,749 total
includes taxes & fees
Aug 7 - Aug 8
2-bedroom 2nd Floor apartment in Mount Joy with off street parking
Working Horse Ranch With Indoor Pool!!
Stunning stone building with a pitched roof, featuring a covered porch and wooden railing.

Working Horse Ranch With Indoor Pool!!

9.4 out of 10, Exceptional, (242)
"Nice lovely vacationWent 5th time."
Working Horse Ranch With Indoor Pool!!
Hershey Trojan, Apt #4 2 Bedroom overlooking the Park
Compact kitchen with modern appliances, dining table, and a window.

Hershey Trojan, Apt #4 2 Bedroom overlooking the Park

9.6 out of 10, Exceptional, (70)
"Philip was an excellent host. He was able to give us early access to the room and it was nice and cool after a hot day at the park. Very spacious and in the heart of Hershey. Would 100% book again in the future. "
The price is ￥22,773
￥37,948 total
includes taxes & fees
Aug 20 - Aug 21
Hershey Trojan, Apt #4 2 Bedroom overlooking the Park
Cocoa Cottage with a Private in-Ground Pool
Welcome to this charming home, featuring a cozy porch with a bench and patriotic flag, surrounded by a beautifully manicured lawn and a shaded tree.

Cocoa Cottage with a Private in-Ground Pool

10.0 out of 10, Exceptional, (231)
"Everything was wonderful. Close to restaurants, and chocolate world. Would definitely stay here again."
Cocoa Cottage with a Private in-Ground Pool
Hershey Family Home in Chocolate town🍫
Relax in this inviting living room with a large flat-screen TV, fireplace, and comfortable seating area.

Hershey Family Home in Chocolate town🍫

8.6 out of 10, Excellent, (43)
"Exactly as advertised, close to everything, would stay here again!"
The price is ￥33,718
￥71,271 total
includes taxes & fees
Aug 10 - Aug 11
Hershey Family Home in Chocolate town🍫
5-bedroom vacation home 12 minutes from Hersheypark
Stunning home with a beautifully manicured front yard, featuring a prominent entrance, a spacious porch, and mature trees.

5-bedroom vacation home 12 minutes from Hersheypark

10.0 out of 10, Exceptional, (15)
"Unique Home We Loved the Location, Home is Huge!"
The price is ￥42,974
￥100,620 total
includes taxes & fees
Sep 2 - Sep 3
5-bedroom vacation home 12 minutes from Hersheypark
Philip Arthur Suite, Apt #6 Hershey Penthouse overlooking all of Hershey
Compact kitchen area with a microwave, stove, and sink, plus a dining table and chairs.

Philip Arthur Suite, Apt #6 Hershey Penthouse overlooking all of Hershey

9.6 out of 10, Exceptional, (58)
"This property was an amazing find! It served all of our needs. The location was perfect to Hershey and the Farm expo for the cheer competition we attended. Thank you so much! "
Philip Arthur Suite, Apt #6 Hershey Penthouse overlooking all of Hershey
Charming 2-Bedroom Retreat Near Hershey
Relax in this stylish living room with a large flat-screen TV, comfortable sofa, and cozy throw blanket.

Charming 2-Bedroom Retreat Near Hershey

10.0 out of 10, Exceptional, (22)
"Everything about this place is wonderful! This was our first time booking a VRBO and it set the bar high. Would recommend this to anyone! "
The price is ￥18,365
￥41,218 total
includes taxes & fees
Aug 10 - Aug 11
Charming 2-Bedroom Retreat Near Hershey
Welcome to The Pearl: Your Perfect Family Getaway! Minutes from Attractions.
Exterior detail

Welcome to The Pearl: Your Perfect Family Getaway! Minutes from Attractions.

2.0 star property
10.0 out of 10, Exceptional, (5)
"Booked the Pearl over MLK weekend to attend a hockey tournament centered in Hershey, PA. The house easily accommodated everyone in our group (6 adults). The house was fully stocked with all the creature comforts (coffee, snacks, laundry detergent, paper towels, toilet paper etc.). Pete was also very accommodating and allowed us a late checkout time that aligned with our tournament schedule. All and all a great location and stay at the pearl. We hope to book again next year! "
The price is ￥41,843
￥85,990 total
includes taxes & fees
Sep 2 - Sep 3
Welcome to The Pearl: Your Perfect Family Getaway! Minutes from Attractions.
Hell's Kitchen, Apt #1 1-bedroom apartment just a short walk to Hershey Theatre
Experience the unique blend of brick and stucco walls in this stylish room, featuring a dining area and steps leading to an upper level.

Hell's Kitchen, Apt #1 1-bedroom apartment just a short walk to Hershey Theatre

9.8 out of 10, Exceptional, (12)
"Very clean, very good área. "
The price is ￥18,071
￥29,349 total
includes taxes & fees
Aug 20 - Aug 21
Hell's Kitchen, Apt #1 1-bedroom apartment just a short walk to Hershey Theatre
Meadow View Cottage
Enjoy a fully equipped kitchen with a central island, refrigerator, and stove, perfect for preparing meals.

Meadow View Cottage

9.4 out of 10, Exceptional, (23)
"Clean, private location, quiet property."
Meadow View Cottage
Ultimate Barn Stay with lots of space! Visit farm animals and 20 min to Hershey!
Relax in this inviting space with a sofa, chair, and flat-screen TV.

Ultimate Barn Stay with lots of space! Visit farm animals and 20 min to Hershey!

9.6 out of 10, Exceptional, (80)
"We had a great time. The location was great and the unit was exactly as advertised. Highly recommended. "
The price is ￥14,148
￥26,159 total
includes taxes & fees
Aug 10 - Aug 11
Ultimate Barn Stay with lots of space! Visit farm animals and 20 min to Hershey!
Modern Farmhouse Getaway Close to Hershey
Fridge, microwave, oven, stovetop

Modern Farmhouse Getaway Close to Hershey

10.0 out of 10, Exceptional, (65)
"Excellent site for family stay. Many amenities and options to enjoy."
The price is ￥24,829
￥54,981 total
includes taxes & fees
Sep 2 - Sep 3
Modern Farmhouse Getaway Close to Hershey
Mountville Rental w/ Private Patio & Gas Grill!
Stroll along the paved walkway to a serene outdoor space surrounded by lush greenery and a charming residential building.

Mountville Rental w/ Private Patio & Gas Grill!

9.8 out of 10, Exceptional, (13)
"We really enjoyed our stay. It was very go again clean and cozy. The host was exremley nice and friendly. Would definitly go again!"
Mountville Rental w/ Private Patio & Gas Grill!
IN-GROUND POOL, Large Private Fenced Yard, Dining Gazebo, Outdoor Kitchen/Bath
Enjoy meals in this well-lit kitchen with a glass-top dining table and white cabinetry.

IN-GROUND POOL, Large Private Fenced Yard, Dining Gazebo, Outdoor Kitchen/Bath

10.0 out of 10, Exceptional, (174)
"Great location with plenty of room for our group"
IN-GROUND POOL, Large Private Fenced Yard, Dining Gazebo, Outdoor Kitchen/Bath
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Middletown Hotel Reviews

Wingate by Wyndham Harrisburg Near Hershey

Wingate by Wyndham Harrisburg Near Hershey

10/10 Excellent
"Family felt safe and cared for."
Anonymous traveler 18-night trip
Posted 12 hours ago
Wingate by Wyndham Harrisburg Near Hershey

Frequently asked questions

Can I find a vacation rental in Middletown?

Yes, there are vacation rentals in Middletown close to Middletown & Hummelstown Railroad, or you can go with a more secluded option if you'd like a relaxing place to stay. Our travelers say Middletown has a good selection of restaurants. Make sure you have time to check out the shopping and bars during your trip.

What are some of the best vacation home rentals that Middletown has to offer?

Working Horse Ranch With Indoor Pool!!: This vacation home rental near Middletown is located in a rural location and has an indoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a patio and a selection of games.

How many vacation rentals are there in Middletown?

With 8 Expedia vacation rentals, you're sure to find just the right place for your Middletown stay.

What’s there to see and do in Middletown?

Explore the area and family-friendly sights such as Hersheypark, or get out into nature at a spot like Susquehanna River. Other places in town to visit include The Vineyard and Brewery at Hershey and Middletown & Hummelstown Railroad.

What’s a vacation rental in Middletown like?

A vacation rental is a private property you can book for several days or longer in Middletown. Vacation rentals provide amenities such as kitchens and laundry facilities so your stay will be comfortable. If you're concerned about a clean environment, vacation rentals can offer a sense of security away from public hotel elevators and lobbies packed with people while still allowing you a great travel experience. You'll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a great option for a small group gathering.