Middletown Vacation Rentals

Start date: Check-in selected.
To Date
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
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Oct 17 - Oct 19
In two months
Nov 28 - Nov 30
In three months
Dec 26 - Dec 28
In four months
Jan 23 - Jan 25

Vacation Rentals in Middletown

Fire Pit, Game Room, 15 min to Hershey with King Bed, Entire house
Terrace/patio

Fire Pit, Game Room, 15 min to Hershey with King Bed, Entire house

10.0 out of 10, Exceptional, (8)
"A very nice and cozy house with perfect facilities"
The price is ￥26,748
￥68,239 total
includes taxes & fees
Oct 13 - Oct 14
Fire Pit, Game Room, 15 min to Hershey with King Bed, Entire house
stayAPT Suites Harrisburg-Hershey
Courtyard

stayAPT Suites Harrisburg-Hershey

3.5 star property
8.6 out of 10, Excellent, (137)
"Great room for the price!! "
The price is ￥16,197
￥17,979 total
includes taxes & fees
Oct 1 - Oct 2
stayAPT Suites Harrisburg-Hershey
Iconic "Haines Shoe House" - Hot Tub & Firepit - Featured On HGTV
Outdoor spa tub

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 ￥20,988
￥59,698 total
includes taxes & fees
Oct 6 - Oct 7
Iconic "Haines Shoe House" - Hot Tub & Firepit - Featured On HGTV
The Suites at Hershey
Indoor pool, seasonal outdoor pool

The Suites at Hershey

3.0 star property
9.2 out of 10, Wonderful, (269)
"Great amenities "
The Suites at Hershey
BurgBnB Riverfront
Loft, 2 Bedrooms, River View | Private kitchen | Full-size fridge, microwave, oven, stovetop

BurgBnB Riverfront

4.0 star property
10.0 out of 10, Exceptional, (1)
The price is ￥24,153
￥26,810 total
includes taxes & fees
Oct 28 - Oct 29
BurgBnB Riverfront
Tranquility: near Carlisle, Harrisburg, Messiah, Lancaster, Hershey attractions
Property grounds

Tranquility: near Carlisle, Harrisburg, Messiah, Lancaster, Hershey attractions

10.0 out of 10, Exceptional, (35)
"Wonderful place to stay. Loved the organization of everything in the house, snacks were great, and everything was clean. "
Tranquility: near Carlisle, Harrisburg, Messiah, Lancaster, Hershey attractions
Cocoa Cottage with a Private in-Ground Pool
Terrace/patio

Cocoa Cottage with a Private in-Ground Pool

10.0 out of 10, Exceptional, (241)
"Great location! Pool and home was clean. Local grocery store and restaurants are all walkable. Will book again next summer if available. "
Cocoa Cottage with a Private in-Ground Pool
Ultimate Barn Stay with lots of space! Visit farm animals and 20 min to Hershey!
Smart TV, books

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

9.6 out of 10, Exceptional, (86)
"We had a wonderful stay! Our kids can't wait to go back. "
The price is ￥8,158
￥19,628 total
includes taxes & fees
Oct 14 - Oct 15
Ultimate Barn Stay with lots of space! Visit farm animals and 20 min to Hershey!
Working Horse Ranch With Indoor Pool!!
Exterior

Working Horse Ranch With Indoor Pool!!

9.4 out of 10, Exceptional, (252)
"We LOVE coming to this house yearly! We come with multiple families and there is so much to keep everyone occupied and only 20 mins to Hershey! Between the pool, game room and garage with sporting stuff, we never hear "we're bored"!"
Working Horse Ranch With Indoor Pool!!
Charming 4-Bedroom Retreat w/ Pool & Playroom, Near Hersheypark & Harrisburg
Pool

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

9.4 out of 10, Exceptional, (10)
"We had a wonderful stay. The house is comfortable (especially for multiple kids), the pool was awesome, and great location central to many places."
Charming 4-Bedroom Retreat w/ Pool & Playroom, Near Hersheypark & Harrisburg
Destination Hershey
Fridge, microwave, oven, stovetop

Destination Hershey

9.2 out of 10, Wonderful, (16)
"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 ￥37,893
￥66,274 total
includes taxes & fees
Oct 1 - Oct 2
Destination Hershey
Sweet Escape on Reese Avenue - 5 minutes away from Hershey Park!
Interior

Sweet Escape on Reese Avenue - 5 minutes away from Hershey Park!

8.8 out of 10, Excellent, (49)
"Cozy"
The price is ￥35,441
￥73,413 total
includes taxes & fees
Oct 1 - Oct 2
Sweet Escape on Reese Avenue - 5 minutes away from Hershey Park!
Hershey Trojan, Apt #4 2 Bedroom overlooking the Park
Fridge, microwave, oven, stovetop

Hershey Trojan, Apt #4 2 Bedroom overlooking the Park

9.6 out of 10, Exceptional, (79)
"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 ￥16,197
￥29,376 total
includes taxes & fees
Oct 13 - Oct 14
Hershey Trojan, Apt #4 2 Bedroom overlooking the Park
5-bedroom vacation home 12 minutes from Hersheypark
Exterior

5-bedroom vacation home 12 minutes from Hersheypark

9.8 out of 10, Exceptional, (19)
"Unique Home We Loved the Location, Home is Huge!"
The price is ￥43,837
￥102,182 total
includes taxes & fees
Oct 20 - Oct 21
5-bedroom vacation home 12 minutes from Hersheypark
Cozy family home, close to all things Hershey and Central Pennsylvania...
Fridge, microwave, oven, stovetop

Cozy family home, close to all things Hershey and Central Pennsylvania...

9.6 out of 10, Exceptional, (156)
"This house was so charming and clean. We enjoyed the area and the closeness to Hersheypark as well as other areas. 100% recommend for your family vacation home!"
The price is ￥39,988
￥87,931 total
includes taxes & fees
Oct 13 - Oct 14
Cozy family home, close to all things Hershey and Central Pennsylvania...
Stay Near Hershey – Family-Friendly Suite for 6 with WiFi, AC and Private Entry
Smart TV

Stay Near Hershey – Family-Friendly Suite for 6 with WiFi, AC and Private Entry

10.0 out of 10, Exceptional, (1)
"The only two issues - had to struggle to lock the sliding door; inability to regulate the A/C - it was extremely cold. Otherwise it was wonderful - clean, cute, confortable beds, well furnished. I’d definitely stay again. I’ll just know to bring warm clothes."
Stay Near Hershey – Family-Friendly Suite for 6 with WiFi, AC and Private Entry
Charming Riverfront Cottage with stunning views of the Susquehanna River
Interior

Charming Riverfront Cottage with stunning views of the Susquehanna River

10.0 out of 10, Exceptional, (352)
"This is an awesome place to stay. The host are top notch an if you send a message asking something about the place they respond quickly. This makes my 4th time staying there an each time was great."
Charming Riverfront Cottage with stunning views of the Susquehanna River
House of Lights
Exterior

House of Lights

9.2 out of 10, Wonderful, (34)
"Super cute house and great location "
The price is ￥10,164
￥30,574 total
includes taxes & fees
Oct 5 - Oct 6
House of Lights
Joyful 5-Bedroom Home w/ Private Backyard
Fridge, microwave, oven, stovetop

Joyful 5-Bedroom Home w/ Private Backyard

9.4 out of 10, Exceptional, (17)
"Excellent experience. The house was beautiful, beds were comfy and even had towels/ bedding included. Glad we stayed. "
The price is ￥37,150
￥82,852 total
includes taxes & fees
Oct 21 - Oct 22
Joyful 5-Bedroom Home w/ Private Backyard
Unique tiny home experience in a one of a kind tiny home community!
Fridge

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

9.4 out of 10, Exceptional, (17)
"It's a cute tiny home. Area is really nice and close to everything."
The price is ￥15,447
￥23,462 total
includes taxes & fees
Oct 1 - Oct 2
Unique tiny home experience in a one of a kind tiny home community!
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Middletown Hotel Reviews

Ramada by Wyndham Harrisburg/Hershey Area

Ramada by Wyndham Harrisburg/Hershey Area

10/10 Excellent
"The room was clean, staff was friendly and our cats had a great stay. Thank you Ramada!!"
Matthew 2-night trip
Posted 1 day ago
Ramada by Wyndham Harrisburg/Hershey Area

Find out more about Middletown

Find out more about Middletown

Search for holiday rentals in Middletown on Expedia! You can easily find your home rentals, villas, holiday apartments in Middletown using one of the methods below:

  • View our selection of featured holiday rentals in Middletown
  • Use the map to find apartments and other holiday homes in the Middletown neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Middletown while they last

Look no further and take a look at our great range of rental properties in Middletown!

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?

Ultimate Barn Stay with lots of space! Visit farm animals and 20 min to Hershey!: Located near Middletown, this vacation home rental is located in a rural location and offers a selection of books, air-conditioning, and a Smart TV to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

How many vacation rentals are there in Middletown?

With 9 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.