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Middletown Holiday Rentals

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Check prices for these dates

In two weeks
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Middletown holiday rentals

Interior

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

Fire Pit, Game Room, 15 min to Hershey with King Bed, Entire house
Middletown
10.0 out of 10, Exceptional, (21 reviews)
"We had 2 families stay together for a sporting event. The house was clean and very cozy. "
United States
Jennifer B.
The price is HK$1,363
HK$4,094 total
includes taxes & fees
2 Sept - 3 Sept
Fire Pit, Game Room, 15 min to Hershey with King Bed, Entire house
Dining

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

*Newly* Renovated Stay at modern 3BR Townhome (15 minutes from Harris-Hershey)
Highspire
9.0 out of 10, Wonderful, (12 reviews)
"The place worked for us well. "
United States
Anonymous traveller
The price is HK$1,448
HK$3,369 total
includes taxes & fees
18 Aug - 19 Aug
*Newly* Renovated Stay at modern 3BR Townhome (15 minutes from Harris-Hershey)
Exterior detail

3. ❤️ Perfect for traveling nurses! - Wifi, AC, 4-6 minute commute to Hershey Med

❤️ Perfect for traveling nurses! - Wifi, AC, 4-6 minute commute to Hershey Med
Hummelstown
10.0 out of 10, Exceptional, (11 reviews)
"Apartment was clean and comfortable."
United States
Dorothy G.
❤️ Perfect for traveling nurses! - Wifi, AC, 4-6 minute commute to Hershey Med
Outdoor dining

4. Cozy Corner Cottage .5 mi from HersheyPark

Cozy Corner Cottage .5 mi from HersheyPark
Union Deposit
10.0 out of 10, Exceptional, (47 reviews)
"Fantastic stay for a family with a dog. So close to Hershey Park."
United States
Corey H.
The price is HK$1,900
HK$3,145 total
includes taxes & fees
16 Aug - 17 Aug
Cozy Corner Cottage .5 mi from HersheyPark
Exterior

5. 5-bedroom vacation home 12 minutes from Hersheypark

5-bedroom vacation home 12 minutes from Hersheypark
Hummelstown
10.0 out of 10, Exceptional, (36 reviews)
"Lots of room for everyone in our party! Enough parking for multiple cars. Host was accommodating with check in as well! "
United States
Lisa P.
The price is HK$2,550
HK$5,690 total
includes taxes & fees
13 Sept - 14 Sept
5-bedroom vacation home 12 minutes from Hersheypark
Coffee/tea maker, fridge, microwave, oven

6. Elizabethtown Ranch House|Hot Tub|Outdoor Dining

Elizabethtown Ranch House|Hot Tub|Outdoor Dining
Elizabethtown
10.0 out of 10, Exceptional, (3 reviews)
"House was very Nice. Our family had a funeral to attend to. It was so nice to have such large nice home so our family could stay together. Rooms were well appointed and very clean!"
United States
Timothy S.
The price is HK$2,276
HK$4,678 total
includes taxes & fees
7 Sept - 8 Sept
Elizabethtown Ranch House|Hot Tub|Outdoor Dining
Outdoor dining

7. Hershey Music Box 2 - Duplex near HersheyPark, Giant Center, Hershey, Palmyra

Hershey Music Box 2 - Duplex near HersheyPark, Giant Center, Hershey, Palmyra
Hummelstown
9.8 out of 10, Exceptional, (13 reviews)
"Our Host was amazing. She met all of our needs. We will definitely book this place again. "
United States
William B.
The price is HK$1,962
HK$3,715 total
includes taxes & fees
8 Sept - 9 Sept
Hershey Music Box 2 - Duplex near HersheyPark, Giant Center, Hershey, Palmyra
Interior

8. The Jolly Rancher

The Jolly Rancher
Hummelstown
10.0 out of 10, Exceptional, (21 reviews)
"The house was beautiful and included many everyday necessities unlike some others I stayed in…garbage bags, zip locks, beach tools for the hot tub etc. Coffee bar was also amazing! Would definitely stay here again. "
United States
Michelle S.
The price is HK$2,456
HK$5,754 total
includes taxes & fees
23 Aug - 24 Aug
The Jolly Rancher
Property grounds

9. The Goldfinch I Luxe Stay for 2 w/ Hot Tub

The Goldfinch I Luxe Stay for 2 w/ Hot Tub
Elizabethtown
10.0 out of 10, Exceptional, (55 reviews)
"The property was just as listed. My husband loved the hot tub. The privacy of the courtyard was very nice. "
United States
Buffie Elaine W.
The price is HK$785
HK$1,897 total
includes taxes & fees
16 Aug - 17 Aug
The Goldfinch I Luxe Stay for 2 w/ Hot Tub
Interior

10. The Cardinal I 2 BR Apartment, Sleeps 4

The Cardinal I 2 BR Apartment, Sleeps 4
Elizabethtown
10.0 out of 10, Exceptional, (37 reviews)
"Great location within a few miles from Hershey. Found great local restaurants too! Very clean and great beds!"
United States
Kelley S.
The price is HK$832
HK$2,044 total
includes taxes & fees
27 Aug - 28 Aug
The Cardinal I 2 BR Apartment, Sleeps 4
Coffee/tea maker, fridge, microwave, oven

11. Hershey Kiss Home

Hershey Kiss Home
Hummelstown
9.8 out of 10, Exceptional, (48 reviews)
"Clean and stock with everything we needed for a weekend in Hershey."
United States
Heather M.
The price is HK$1,985
HK$3,742 total
includes taxes & fees
30 Aug - 31 Aug
Hershey Kiss Home
Dining

12. Elizabethtown Guest house|HOT TUB|SAUNA

Elizabethtown Guest house|HOT TUB|SAUNA
Elizabethtown
9.2 out of 10, Wonderful, (5 reviews)
"Very clean, lovely decor. Responsive host. "
United States
Hanna
The price is HK$1,872
HK$3,942 total
includes taxes & fees
20 Aug - 21 Aug
Elizabethtown Guest house|HOT TUB|SAUNA
Terrace/patio

13. In the heart of Hershey!

In the heart of Hershey!
Hershey
10.0 out of 10, Exceptional, (4 reviews)
"Quiet, clean, comfortable and private. Excellent booking. "
United States
Michael S.
The price is HK$2,982
HK$6,011 total
includes taxes & fees
26 Aug - 27 Aug
In the heart of Hershey!
Exterior

14. Hersheypark in 2 miles,w/ large private yard

Hersheypark in 2 miles,w/ large private yard
Downtown Hershey
9.8 out of 10, Exceptional, (10 reviews)
"Extremely clean home very close to Hersey Park! Great value, comfortable, and couldn’t be more perfect for touring Hersey Park and the area. House description is accurate. Would stay here again!"
United States
Lauren M.
The price is HK$1,201
HK$2,893 total
includes taxes & fees
19 Aug - 20 Aug
Hersheypark in 2 miles,w/ large private yard
Coffee/tea maker, fridge, microwave, oven

15. Located right at the center of Elizabethtown , Lancaster, York and Hershey park.

Located right at the center of Elizabethtown , Lancaster, York and Hershey park.
Elizabethtown
10.0 out of 10, Exceptional, (47 reviews)
"The property was perfect for us. It had everything we needed, was comfortable, clean and spacious. We will definitely be back."
United States
Robert T.
The price is HK$1,412
HK$3,568 total
includes taxes & fees
2 Sept - 3 Sept
Located right at the center of Elizabethtown , Lancaster, York and Hershey park.
Coffee/tea maker, fridge, microwave, oven

16. Modern Farmhouse Getaway I 2 BR, Sleeps 6

Modern Farmhouse Getaway I 2 BR, Sleeps 6
Elizabethtown
10.0 out of 10, Exceptional, (86 reviews)
"Was awesome, quiet, clean, kitchen stocked, beds very comfortable. "
United States
Sharon W.
The price is HK$1,036
HK$2,573 total
includes taxes & fees
17 Aug - 18 Aug
Modern Farmhouse Getaway I 2 BR, Sleeps 6
Indoor pool, seasonal outdoor pool

17. Bluegreen Vacations Suites at Hershey, an Ascend Collection Resort

Bluegreen Vacations Suites at Hershey, an Ascend Collection Resort
3.0 star property
North Hershey
9.2 out of 10, Wonderful, (303 reviews)
"Family friendly"
United States
Cierra
The price is HK$2,061
HK$2,288 total
includes taxes & fees
9 Sept - 10 Sept
Bluegreen Vacations Suites at Hershey, an Ascend Collection Resort
Exterior

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

Sweet Escape on Reese Avenue - 5 minutes away from Hershey Park!
Downtown Hershey
8.6 out of 10, Excellent, (64 reviews)
"The House was roomy, clean, close to Hershey. The beds were super comfy"
United States
Megan K.
The price is HK$1,801
HK$3,512 total
includes taxes & fees
16 Aug - 17 Aug
Sweet Escape on Reese Avenue - 5 minutes away from Hershey Park!
Interior

19. 2 Full Bed|Smk|New Cumberland, PA

2 Full Bed|Smk|New Cumberland, PA
New Cumberland, PA
10.0 out of 10, Exceptional, (38 reviews)
"Ideal spot for an overnight stay! Can't beat the access to nearby attractions."
United States
Anonymous traveller
The price is HK$667
HK$819 total
includes taxes & fees
19 Aug - 20 Aug
2 Full Bed|Smk|New Cumberland, PA
Smart TV, books, offices, computer monitors

20. Family Friendly, Peaceful Yard, Dedicated Work Space, Close to Local Attractions

Family Friendly, Peaceful Yard, Dedicated Work Space, Close to Local Attractions
New Cumberland
9.6 out of 10, Exceptional, (21 reviews)
"This was the perfect property for us to stay while we were in town visiting for a graduation weekend. Plenty of space for everyone, plenty of necessities in the kitchen. Cute little house on a quiet street and a quiet neighborhood, but close to everything. We would definitely stay here again."
United States
Shannon N.
The price is HK$1,236
HK$2,880 total
includes taxes & fees
16 Aug - 17 Aug
Family Friendly, Peaceful Yard, Dedicated Work Space, Close to Local Attractions
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

Tru By Hilton Hershey Chocolate Avenue

Tru By Hilton Hershey Chocolate Avenue

10/10 Excellent
"The room was very clean and beds were comfortable."
Jennifer 3-night trip
Posted 9 hours ago
Tru By Hilton Hershey Chocolate Avenue

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 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?

Luxury Angus Ranch Estate • Pool & HotTub • Private 50-Acre Retreat Near Hershey: This holiday home rental outside Middletown offers an outdoor pool, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

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 Middletown & Hummelstown Railroad and The Vineyard and Brewery at Hershey.

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.