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

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Middletown cottages

A wooden deck with a hot tub, lounge chairs, and a view of the water.

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

Long Beach Cottage, (romantic couple’s getaway)
Charlestown
10.0 out of 10, Exceptional, (8 reviews)
"Nice, quaint house, right on the water. Perfect for couples looking to relax. "
United States
Mike F.
$442 nightly
The price is $463
Nov 9 - Nov 10
Total with taxes and fees
Long Beach Cottage, (romantic couple’s getaway)
A residential area with houses, a parking lot, and a body of water in the background.

2. 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, (18 reviews)
"Was a great stay would definitely stay again "
United States
jerel p.
$192 nightly
The price is $204
Nov 9 - Nov 10
Total with taxes and fees
Quarry Landing - Center of Town & River View - 3 Bedroom
A two-story house with a deck, a barbecue grill, and a covered patio area.

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

Thunder Hill Retreat - Spacious/Deck/Hot tub
Lincoln University
10.0 out of 10, Exceptional, (25 reviews)
"Great place to get away! Peaceful, serene with amenities to boast!"
United States
Arthur B.
$433 nightly
The price is $480
Nov 9 - Nov 10
Total with taxes and fees
Thunder Hill Retreat - Spacious/Deck/Hot tub
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

DoubleTree by Hilton Downtown Wilmington - Legal District

DoubleTree by Hilton Downtown Wilmington - Legal District

10/10 Excellent
"Good"
carlton 1-night trip
Posted 6 hours ago
DoubleTree by Hilton Downtown Wilmington - Legal District

Find out more about Middletown

Middletown Cottages information

Number of reviews
26
Accommodation
24 Cottages
Lowest Price
$204
Highest Price
$480

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.

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