Middletown Holiday Rentals

Start date: Check-in selected.
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Holiday Rentals in Middletown

Our top choices for Middletown holiday rentals

stayAPT Suites Harrisburg-Hershey

3.5 star property
8.6 out of 10, Excellent, (128)
"Great room for the price!! "
The price is AU$186
includes taxes & fees
4 Sept - 5 Sept
stayAPT Suites Harrisburg-Hershey

The Suites at Hershey

3.0 star property
9.2 out of 10, Wonderful, (265)
"Great amenities "
The Suites at Hershey

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

10.0 out of 10, Exceptional, (122)
"This was a great overnight in a cute spot that we have seen along the higheay for years. Glad our fanily was finally able to check it out!"
The price is AU$634
includes taxes & fees
4 Sept - 5 Sept
Iconic "Haines Shoe House" - Hot Tub & Firepit - Featured On HGTV

Get Hershey Park Happy at Penbrook Alley!

2.0 star property
10.0 out of 10, Exceptional, (2)
"Great property with an ideal location to get around Harrisburg and Hershey. "
The price is AU$488
includes taxes & fees
8 Sept - 9 Sept
Get Hershey Park Happy at Penbrook Alley!

Hershey Trojan, Apt #4 2 Bedroom overlooking the Park

9.6 out of 10, Exceptional, (75)
"I had a good stay was very clean and great location, thank you very much and I would come back and will share with others "
The price is AU$342
includes taxes & fees
9 Sept - 10 Sept
Hershey Trojan, Apt #4 2 Bedroom overlooking the Park

Hershey happiness less than 5 miles to the park!

10.0 out of 10, Exceptional, (81)
"This house may be the cleanest rental I’ve ever stayed in. It’s an older home that has a lot of coziness to it. The beds were very comfortable and there was plenty of room for the four of us. Its location is really convenient to Hershey attractions and restaurants. "
The price is AU$473
includes taxes & fees
15 Sept - 16 Sept
Hershey happiness less than 5 miles to the park!

Fun, Family-friendly Home With A 20x40 Pool 12 Minutes From Hershey Attractions

10.0 out of 10, Exceptional, (251)
"I had a great stay and had great family time. Thank you"
Fun, Family-friendly Home With A 20x40 Pool 12 Minutes From Hershey Attractions

Cocoa Cottage with a Private in-Ground Pool

10.0 out of 10, Exceptional, (241)
"We had the pleasure of staying here over a long holiday weekend. The home was all you would want and more. It was well stocked, clean, and in a great location. Restaurants, coffee shops and many attractions were located near by. The host was a pleasure to deal with and we are looking forward to our next visit! "
Cocoa Cottage with a Private in-Ground Pool

Historic Riverfront Vintage Gem

4.0 star property
The price is AU$321
includes taxes & fees
15 Sept - 16 Sept
Historic Riverfront Vintage Gem

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

2.0 star property
9.6 out of 10, Exceptional, (20)
"Cozy accommodations and quiet but bustling area! Definitely made the trip more enjoyable!! Would definitely stay again next time I’m in the area! "
The price is AU$239
includes taxes & fees
4 Sept - 5 Sept
2-bedroom 2nd Floor apartment in Mount Joy with off street parking

Destination Hershey

9.0 out of 10, Wonderful, (13)
"We stayed overnight in this adorable house with our kids and grandchildren. Perfect location, and the house was exactly what we needed. We would definitely come back! Also loved the convenience of the brewery/restaurant next door! It snowed while we were there, only adding to the magic of the Christmas season! "
The price is AU$612
includes taxes & fees
8 Sept - 9 Sept
Destination Hershey

Charming 4-Bedroom Retreat w/ Pool & Playroom, Near Hersheypark & Harrisburg

9.4 out of 10, Exceptional, (9)
Charming 4-Bedroom Retreat w/ Pool & Playroom, Near Hersheypark & Harrisburg

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

9.6 out of 10, Exceptional, (84)
"We had a wonderful stay! Our kids can't wait to go back. "
The price is AU$239
includes taxes & fees
8 Sept - 9 Sept
Ultimate Barn Stay with lots of space! Visit farm animals and 20 min to Hershey!

Parkview, Apt #5 Parkview Historic Apartment

9.6 out of 10, Exceptional, (30)
"Great location. Close to literally everything. Will def be back. "
The price is AU$233
includes taxes & fees
29 Sept - 30 Sept
Parkview, Apt #5 Parkview Historic Apartment

Hershey Park Friendly Loge Unit 2

2.0 out of 10, (5)
The price is AU$308
includes taxes & fees
14 Sept - 15 Sept
Hershey Park Friendly Loge Unit 2

Near York expo center. It’s half a mile walk to the Carlisle ave entrance.

10.0 out of 10, Exceptional, (4)
"Nice place. Short distance to the York State Fair. "
The price is AU$197
includes taxes & fees
15 Sept - 16 Sept
Near York expo center. It’s half a mile walk to the Carlisle ave entrance.

House of Lights

9.2 out of 10, Wonderful, (28)
"Was an enjoyable stay with good accommodations."
The price is AU$316
includes taxes & fees
4 Sept - 5 Sept
House of Lights

Unique tiny home experience in a one of a kind tiny home community!

9.4 out of 10, Exceptional, (16)
"It's a cute tiny home. Area is really nice and close to everything."
The price is AU$245
includes taxes & fees
4 Sept - 5 Sept
Unique tiny home experience in a one of a kind tiny home community!

An adorable tiny home perfect for your tiny getaway!

9.6 out of 10, Exceptional, (20)
"We had a lovely stay. We were excited to stay in a tiny house. We were comfortable."
The price is AU$247
includes taxes & fees
7 Sept - 8 Sept
An adorable tiny home perfect for your tiny getaway!

Quiet studio apt w large deck. 15 min to Lanc city, >10 to Spooky Nook Sports

10.0 out of 10, Exceptional, (1)
"Such an adorable place! It feels much more spacious and even cozier than the pictures let on. The host was super accommodating and responsive. Lots of good eating spots very nearby!"
The price is AU$237
includes taxes & fees
4 Sept - 5 Sept
Quiet studio apt w large deck. 15 min to Lanc city, >10 to Spooky Nook Sports
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Middletown Hotel Reviews

Find out more about Middletown

Find out more about Middletown

Everything you need to know about Middletown holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Middletown holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Middletown holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Middletown holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Middletown. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Middletown holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Middletown holiday rentals we have selected for you start as low as AU$186 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Middletown rentals

At Expedia, we put the best Middletown holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Middletown rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Middletown holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Middletown. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find a holiday rental in Middletown?

Yes, there are holiday rentals in Middletown close to Middletown & Hummelstown Railroad, or you can select a more secluded option if you're looking for a relaxing stay. Our travellers 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 holiday rentals that Middletown has to offer?

Ultimate Barn Stay with lots of space! Visit farm animals and 20 min to Hershey!: This holiday home rental outside of Middletown is located in a rural location, and offers a selection of books, air conditioning and free WiFi to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

How many holiday rentals are there in Middletown?

With 8 Expedia holiday rentals, you're guaranteed 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 holiday rental in Middletown like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Middletown. Holiday rentals provide amenities such as patios, hot tubs and fire pits so you'll have a home away from home. If you're concerned about cleanliness, holiday rentals can offer a sense of security away from public hotel lifts and busy concierge desks while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive choice for family trips.