A steel arch bridge over a river with surrounding trees and buildings.

Search Middletown Cottages

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Aug 14 - Aug 16
In two months
Sep 25 - Sep 27
In three months
Oct 23 - Oct 25
In four months
Nov 20 - Nov 22

Our top choices for Middletown cottages

House (3 Bedrooms) | Interior

1. Dover Home Base: 3 Mi to Motor Speedway!

Dover Home Base: 3 Mi to Motor Speedway!
3.0 star property
Dover
$427 nightly
The price is $427
Aug 2 - Aug 3
Total with taxes and fees
Dover Home Base: 3 Mi to Motor Speedway!
Exterior

2. Thunder Hill Retreat - Spacious/Deck/Hot tub

Thunder Hill Retreat - Spacious/Deck/Hot tub
Lincoln University
10.0 out of 10, Exceptional, (24 reviews)
"Everything was good. Had a great time."
United States
Todd H.
$463 nightly
The price is $512
Aug 3 - Aug 4
Total with taxes and fees
Thunder Hill Retreat - Spacious/Deck/Hot tub
Terrace/patio

3. Long Beach Cottage, (romantic couple’s getaway)

Long Beach Cottage, (romantic couple’s getaway)
Charlestown
10.0 out of 10, Exceptional, (6 reviews)
"Nice, quaint house, right on the water. Perfect for couples looking to relax. "
United States
Mike F.
$697 nightly
The price is $733
Aug 11 - Aug 12
Total with taxes and fees
Long Beach Cottage, (romantic couple’s getaway)
Property grounds

4. Quarry Landing - Center of Town & River View - 3 Bedroom

Quarry Landing - Center of Town & River View - 3 Bedroom
Port Deposit
10.0 out of 10, Exceptional, (14 reviews)
"Was a great stay would definitely stay again "
United States
jerel p.
$292 nightly
The price is $310
Aug 4 - Aug 5
Total with taxes and fees
Quarry Landing - Center of Town & River View - 3 Bedroom
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

Great Wolf Lodge Perryville

Great Wolf Lodge Perryville

10/10 Excellent
"Ay mucho entretenimiento en solo lugar para los niños eso me guato"
Yaneth 1-night trip
Posted less than an hour ago
Great Wolf Lodge Perryville

Find out more about Middletown

Middletown Cottages information

Number of reviews
44
Accommodation
24 Cottages
Lowest Price
$310
Highest Price
$733

Frequently asked questions

Why book your cottage in Middletown with Expedia?
Expedia has some terrific cottages in Middletown, so start planning for a memorable vacay close to nature. If you have a set budget, select how much you'd like to spend and the preferred star rating of your property. Or, make use of our filters to search for cottages with a kitchen or a pool. We'll help you find the perfect fit whatever your plans or style of travel.
How can I find cheap cottages in Middletown?
Expedia can help you locate cheap cottages in Middletown. To lock in a fantastic stay in a few quick clicks, try out our convenient filter tool to tailor your search results by budget, star rating and amenities.
What is there to do in Middletown near my cottage?
Once you've unpacked your bags, venture out and discover the wonderful things Middletown has on offer. Frog Hollow Golf Club is a top attraction to add to your must-do list.

Explore a world of travel with Expedia