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Check prices for these dates

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

Our top choices for Middletown cottages

A two-story house with a front lawn and trees in the background.

1. Walk to Stores: Home in Historic Shepherdstown!

Walk to Stores: Home in Historic Shepherdstown!
3.0 star property
Shepherdstown
The price is Rp2.188.769
Rp6.424.851 total
includes taxes & fees
19 Nov - 20 Nov
Walk to Stores: Home in Historic Shepherdstown!
A covered porch with wooden benches, a red mailbox, and a view of a park with trees and a fence.

2. Rural & Historic Detour Escape w/ Horses On-site!

Rural & Historic Detour Escape w/ Horses On-site!
3.0 star property
Keymar
The price is Rp2.948.507
Rp7.816.619 total
includes taxes & fees
13 Nov - 14 Nov
Rural & Historic Detour Escape w/ Horses On-site!
A stone house with a white picket fence, a front porch, and potted plants.

3. Cottage w/ Furnished Patio & Garden: Dtwn Leesburg

Cottage w/ Furnished Patio & Garden: Dtwn Leesburg
3.0 star property
Leesburg's Old and Historic District
The price is Rp7.362.223
Rp12.283.516 total
includes taxes & fees
22 Nov - 23 Nov
Cottage w/ Furnished Patio & Garden: Dtwn Leesburg
A two-story house with a front porch, a garage, and a driveway.

4. Large Family Home: 5 Mi to Dtwn Hagerstown!

Large Family Home: 5 Mi to Dtwn Hagerstown!
3.0 star property
Williamsport
10.0 out of 10, Exceptional, (1 review)
"The place was just beautiful "
United States
Derrick
Large Family Home: 5 Mi to Dtwn Hagerstown!
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

Nestled in the scenic Middletown Valley, this historic town offers charming Main Street shops and the annual Middletown Heritage Festival each September. Outdoor enthusiasts can explore nearby South Mountain State Park's hiking trails or visit local wineries for tastings with spectacular valley views.

See all hotels in Middletown
A stone tower with a staircase leading up to it.

Top reviews in Middletown

A Hampton Inn & Suites hotel with a modern facade, large columns, and a well-lit entrance.
Hampton Inn & Suites Frederick-Fort Detrick

Hampton Inn & Suites Frederick-Fort Detrick

Hampton Inn & Suites Frederick-Fort Detrick
Frederick

10/10 Excellent

Staff was great! Helpful and polite.
United Kingdom
Ana
Reviewed May 8, 2024
Hampton Inn & Suites Frederick-Fort Detrick

Frequently Asked Questions

Why book your cottage in Middletown with Expedia?

Reserving a cottage in Middletown is as simple as working out your travel dates and picking your ideal place for outdoor recreation and relaxation. From luxurious retreats to inexpensive properties and cottages that offer amenities like a kitchenette, Expedia has something for all traveller tastes. As for terrific deals? We've have them as well!

How can I find cheap cottages in Middletown?

With Expedia's helpful filter tool, booking cheap cottages in Middletown is a cinch. To find stays that are friendly on the wallet, narrow your search by star rating, amenities and budget.

What is there to do in Middletown near my cottage?

If you're ready to fill up your itinerary in Middletown, check out Maryland National Golf Club. It's a winner with locals and travellers alike.