Search Middletown Cottage Rentals from CA $183

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Check prices for these dates

Next weekend
Nov 13 - Nov 15
In two weeks
Nov 20 - Nov 22
In one month
Dec 4 - Dec 6
In two months
Jan 1 - Jan 3

Our top choices for Middletown cottages

A two-story house with a covered porch and a staircase leading to the upper level.

1. Creek side cottage with awesome porch and fire pit

Creek side cottage with awesome porch and fire pit
Mechanicsburg
9.8 out of 10, Exceptional, (101 reviews)
"It’s a nice place for family vocation!"
United States
Jing Y.
The price is CA $184
CA $347 total
includes taxes & fees
Nov 16 - Nov 17
Creek side cottage with awesome porch and fire pit
A unique, modern building with a curved facade, a central entrance with a staircase, and a small porch area.

2. Iconic Haines Shoe House - Hot Tub, Firepit, Foosball & 300 Game Arcade Machine!

Iconic Haines Shoe House - Hot Tub, Firepit, Foosball & 300 Game Arcade Machine!
Yorkana
10.0 out of 10, Exceptional, (157 reviews)
"We had a great time at the Shoe House! It was a fun and unique experience!"
United States
Janelle C.
The price is CA $245
CA $605 total
includes taxes & fees
Nov 11 - Nov 12
Iconic Haines Shoe House - Hot Tub, Firepit, Foosball & 300 Game Arcade Machine!
A stone house with a gabled roof and a front porch.

3. Fun & Unique Home w/ Vintage Game Room in Annville

Fun & Unique Home w/ Vintage Game Room in Annville
3.0 star property
Annville
9.0 out of 10, Wonderful, (2 reviews)
"Awesome party space with a massive kitchen. Will definitely boom again in the future. A little pricey, but so worth it for all you get."
United States
Mya
The price is CA $381
CA $1,372 total
includes taxes & fees
Nov 12 - Nov 13
Fun & Unique Home w/ Vintage Game Room in Annville
A stone house with a covered patio and string lights.

4. Stone Cottage at Roundtop Estate couples Retreat with hot tub

Stone Cottage at Roundtop Estate couples Retreat with hot tub
Wrightsville
10.0 out of 10, Exceptional, (11 reviews)
"I had a terrific stay , the cottage was so cozy. Decorated beautifully, the views were amazing I had a wonderful relaxing vacation. "
United States
Leslie A.
The price is CA $340
CA $519 total
includes taxes & fees
Nov 10 - Nov 11
Stone Cottage at Roundtop Estate couples Retreat with hot tub
A large, historic stone house with a turret and red roof, surrounded by well-maintained lawns and trees.

5. 8 Mi to Hersheypark: 'millard Mansion' in Annville

8 Mi to Hersheypark: 'millard Mansion' in Annville
3.0 star property
Annville
10.0 out of 10, Exceptional, (1 review)
"We needed a place to be able to have plenty of room and give us the opportunity to relax. This was the perfect rental for us and I’m sure would be the right place for many others. Highly recommended. "
United States
Tim
The price is CA $766
CA $1,988 total
includes taxes & fees
Nov 12 - Nov 13
8 Mi to Hersheypark: 'millard Mansion' in Annville
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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Learn more about Middletown

Sip local wines and craft beers at The Vineyard and Brewery at Hershey, then hop aboard the historic Middletown & Hummelstown Railroad for a scenic journey. Families can enjoy Doc's Family Fun Centre while weekend visitors shouldn't miss Saturday's Market, all just a short drive from the thrilling rides at Hersheypark.

See all hotels in Middletown
An aerial view of a town with a river, a bridge, and various buildings.

Frequently Asked Questions

How much do cottages in Middletown cost?

Cottages in Middletown range between CA $183 and CA $765 per night. These stays offer a chance to soak in nature's beauty — at a price you can afford. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.

Why book your cottage in Middletown with Expedia?

We think that traveling should be a piece of cake, so if you're on the lookout for cottages in Middletown at a competitive rate, Expedia can help. Keep the budget in check and check in to a wallet-friendly option far away from the downtown buzz, or book a 5-star cottage to spoil your favorite people.

How can I find cheap cottages in Middletown?

The best way to track down cheap cottages in Middletown is with Expedia's useful filter tool. Refine your search by amenities, star rating and budget to nab excellent rates in just a few keystrokes.

What is there to do in Middletown near my cottage?

If you'd like to make the most of your time in Middletown, check out The Vineyard and Brewery at Hershey. It's a winner with locals and visitors alike.

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