Middletown Holiday Rentals

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Holiday Rentals in Middletown

Property grounds
Iconic "Haines Shoe House" - Hot Tub & Firepit - Featured On HGTV!
10.0 out of 10, Exceptional, (70)
"We all had a good time. Weather wasn't that great but we enjoyed the hot tub and firepit regardless."
The price is NZ$887
includes taxes & fees
23 May - 24 May
Iconic "Haines Shoe House" - Hot Tub & Firepit - Featured On HGTV!
Exterior
Insta-Worthy! Funky & Fabulous Cottage with Striking, One-of-a-Kind Design! NEW
10.0 out of 10, Exceptional, (22)
"This was my second time at this cottage and hope to stay again. It rained the whole time! But, with such a cozy place to read and relax, listen to the rain and enjoy the ambiance it was lovely. I walked for a nice dinner at the Hideaway. I walked to Mt Gretna Mercantile for a few treats and always enjoy chatting with the sweet owners. I had an incredible lunch at Porch and Pantry. All without getting in my car. I highly recommend!"
Insta-Worthy! Funky & Fabulous Cottage with Striking, One-of-a-Kind Design! NEW
Interior
Hershey Family Home in Chocolate town🍫
10.0 out of 10, Exceptional, (1)
"One can truly smell the Reese's in the air. Great location to get to Hershey Park campus. We had a lovely stay."
The price is NZ$701
includes taxes & fees
18 May - 19 May
Hershey Family Home in Chocolate town🍫
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Fridge, microwave, oven, stovetop
Meadow View Cottage
10.0 out of 10, Exceptional, (4)
"We enjoyed every bit of our stay! Everything about the cottage was adorable and relaxing. We hope to stay again someday!"
Meadow View Cottage
Property grounds
Farmstay with pool and firepit
10.0 out of 10, Exceptional, (169)
"This beautiful farm stay comes as advertised. There are so many layers of beauty to this stay from the cabin, to the location, to the farm animals, that you can't help but hear God's whisper in all of it. My partner and I were delighted with our stay and are already planning on when we can return. This is a worthwhile investment."
Farmstay with pool and firepit
Fridge, microwave, oven, stovetop
Hershey happiness less than 5 miles to the park!
10.0 out of 10, Exceptional, (22)
"Our family decided to find a place to stay somewhere in the middle of where we all live, and found this sweet place near Hershey, PA. We were thinking about staying in Lancaster, but found this and changed our plans. Six adults and two young children were perfectly comfortable here and we still had one empty bed since we had a pack 'n play for our one year old granddaughter. There is a bedroom downstairs with the bathroom right next to it and then two more bedrooms upstairs with another...
The price is NZ$474
includes taxes & fees
27 May - 28 May
Hershey happiness less than 5 miles to the park!
Property grounds
Beautiful Mount Joy Cabin w/ Pool + Sauna!
10.0 out of 10, Exceptional, (17)
"Spacious, clean, private, and well laid out. Love it. Will go back in future"
Beautiful Mount Joy Cabin w/ Pool + Sauna!
Exterior
Mountain Stone Manor 7 Miles to Hershey and Close to Lancaster
10.0 out of 10, Exceptional, (127)
"Nice place to stay."
Mountain Stone Manor 7 Miles to Hershey and Close to Lancaster
Fridge, microwave, oven, stovetop
Hershey Park and amenities 2 miles away!
10.0 out of 10, Exceptional, (86)
"Our third stay in 'our Palmyra house'. Always the same....a welcoming hostess, exceptionally clean, a well-stocked kitchen. The addition of a washer/dryer is a plus as we stay for an extended time. Already planned our October getaway!"
Hershey Park and amenities 2 miles away!
Pool
Cozy, 4 bedroom, 2 1/2 bath, Hot tub/Swim spa, 10 minutes to Hershey attractions
10.0 out of 10, Exceptional, (42)
"Our group of friends had a wonderful stay! Everything about this home exceeded our expectations! The house was very clean and had plenty of room for our group of 6. The kitchen was very well stocked with everything we needed and our group also enjoyed viewing the stars at night in the very large hot tub! We enjoyed visiting Hershey for dinner and also ventured to a local farm to pick tulips. This home was fantastic and I 100% recommend staying here! Thank you to Mark and Carol for making our...
Cozy, 4 bedroom, 2 1/2 bath, Hot tub/Swim spa, 10 minutes to Hershey attractions
Exterior
Beautiful open and spacious ranch home in country setting
10.0 out of 10, Exceptional, (61)
"This is a lovely, welcoming home with plenty of room for family. We had no complaints at all. We were in PA for the funeral of a wonderful man, brother in law. Sad reason for a road trip but a lovely destination. We will def stay again if the opportunity arises."
Beautiful open and spacious ranch home in country setting
Fridge, microwave, oven, stovetop
Modern Farmhouse Getaway Close to Hershey
10.0 out of 10, Exceptional, (41)
"Amazing property. Thank you for sharing and helping our family make core memories."
The price is NZ$518
includes taxes & fees
27 May - 28 May
Modern Farmhouse Getaway Close to Hershey
Exterior
Creek side cottage with awesome porch and fire pit
10.0 out of 10, Exceptional, (35)
"We enjoyed staying at Lynne's property along a beautiful creek (even if the weather didn't allow us to enjoy it fully). The house was spacious for our family and convenient to the event we were attending in Mechanicsburg. We would recommend it to others. Our interactions with Lynne went smoothly."
The price is NZ$403
includes taxes & fees
20 May - 21 May
Creek side cottage with awesome porch and fire pit
4 bedrooms, iron/ironing board, travel cot, free WiFi
Charming Riverfront Cottage with stunning views of the Susquehanna River
10.0 out of 10, Exceptional, (309)
"We were up here on a weekend fishing trip with some buddies. This was the perfect place for us to stay and had everything we needed. The Host was very responsive and a pleasure to deal with."
Charming Riverfront Cottage with stunning views of the Susquehanna River
Fridge, microwave, stovetop, coffee/tea maker
Pet-Friendly Pennsylvania Retreat w/ Fire Pit!
10.0 out of 10, Exceptional, (5)
"Its a cute house very clean perfect for what we needed it for. We went to visit family and we were just miles to where we needed to go! We will use this place again if its available. Thank you!!"
Pet-Friendly Pennsylvania Retreat w/ Fire Pit!
Pool
HARRISBURG HERSHEY PARK GIANT CENTER FARM SHOW PETS WELCOME GATED YARD SAFE FUN
10.0 out of 10, Exceptional, (76)
"Very clean, charming and comfortable stay- for parents and three adult children and two small dogs. Stayed for son’s graduation from Penn State- Harrisburg. It is in a busy area but inside was private and location close to everything and perfect hangout for kids downstairs. Enjoyed outdoor space and fenced areas for dogs. Would definitely stay again and recommend!"
HARRISBURG HERSHEY PARK GIANT CENTER FARM SHOW PETS WELCOME GATED YARD SAFE FUN
Beach
Riverfront, Mountain View, Private Dock, Kayaks - Hershey, Amish, Gettysburg
10.0 out of 10, Exceptional, (253)
"I chose to stay here for a conference in Hershey and turn it into a little weekend getaway with friends for my husband and kids. We loved the quiet location and the amazing view of the River. Janice and Dave were extremely helpful and available if we had any questions. They bought a new fire pit since the fire pit by the water was wet, provided fishing rods for our daughter and worms to go fishing at the nearby trout hatchery, offered a bike to my daughter and a book for bedtime. The little...
Riverfront, Mountain View, Private Dock, Kayaks - Hershey, Amish, Gettysburg
Fridge, microwave, oven, stovetop
3 Miles to Hersheypark - Crickie's Corner
9.8 out of 10, Exceptional, (41)
"Much older home with 2 bathrooms ,one on second floor and one on third floor . There was an awful smell coming from the tub on 3rd, floor. My son being a plumber said it was not vented properly. Bedrooms were all upstairs 2nd and 3rd floor, very comfortable beds and clean, Stairs were narrow and hard to climb for the older ones staying, especially just to go to bathroom. Only 1 parking space for property so any extra vehicles had to park elsewhere away from the house, We had to be dropped off...
The price is NZ$721
includes taxes & fees
20 May - 21 May
3 Miles to Hersheypark - Crickie's Corner
Private kitchen
Modern Mount Gretna Cottage with Cool Minimalist Design
9.8 out of 10, Exceptional, (35)
"We really enjoyed our stay. The cottage was spacious for us and the beds were comfortable. I thought it could have been a little cleaner. There were some cobwebs around the house. Overall though it was a lovely experience."
Modern Mount Gretna Cottage with Cool Minimalist Design
Exterior
Cozy Wrightsville Cottage w/ Private Hot Tub!
9.8 out of 10, Exceptional, (27)
"I needed a few days of peace and quiet and this place was perfect. Being in the hot tub while looking uo and the stars was so relaxing. The history behind the house is awesome with it being an old school house. Thank you for a peaceful weekend, we did not want to leave!"
Cozy Wrightsville Cottage w/ Private Hot Tub!
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See all available properties in Middletown
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.

Other types of properties in Middletown you may be interested in

Exterior
Fairfield Inn & Suites by Marriott Harrisburg International Airport
2.5 star property
9.0 out of 10, Wonderful, (821)
"Clean, fresh smell, quiet, and just five minutes walking to the airport terminal. "
The price is NZ$216
includes taxes & fees
9 Jun - 10 Jun
Fairfield Inn & Suites by Marriott Harrisburg International Airport
Suite, 1 King Bed, Non Smoking, Jetted Tub
Country Inn & Suites by Radisson, Harrisburg Northeast - Hershey
3.0 star property
8.4 out of 10, Very good, (1000)
"Quick and smooth check-in. Nice room for the price."
The price is NZ$168
includes taxes & fees
29 May - 30 May
Country Inn & Suites by Radisson, Harrisburg Northeast - Hershey
Exterior
La Quinta Inn & Suites by Wyndham Harrisburg-Hershey
2.5 star property
7.8 out of 10, Good, (951)
"Very friendly welcome. Fresh cookies at check-in. Room was perfect. Very quiet."
The price is NZ$129
includes taxes & fees
20 May - 21 May
La Quinta Inn & Suites by Wyndham Harrisburg-Hershey
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Middletown holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Middletown. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Middletown. Seeing all the best attractions is bound to make you fall in love with Middletown. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Middletown short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find a holiday rental in Middletown?

Yes, we give you a choice of holiday rentals where you'll be only 7.3 mi (11.8 km) from Hersheypark, giving you a secluded option if you want a quiet place to 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?

Hershey Family Home in Chocolate town🍫: This holiday home rental outside of Middletown has air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

How many holiday rentals are there in Middletown?

With 12 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.

Recent reviews of Middletown properties
Expedia verified reviews