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Jul 4 - Jul 6
In two weeks
Jul 11 - Jul 13
In one month
Jul 25 - Jul 27
In two months
Aug 22 - Aug 24

Cottages in Middletown

Chesapeake Romantic Waterfront Home with Private Pool
Fireplace

Chesapeake Romantic Waterfront Home with Private Pool

9.0 out of 10, Wonderful, (6)
"Great communication, easy to access, accommodations true to listing. Spacious, renovated living space. Great outdoor pool."
Chesapeake Romantic Waterfront Home with Private Pool
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Smart TV, books

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

9.8 out of 10, Exceptional, (50)
"This was our second time staying at the property with our two kids and the accommodations continue to impress. We will happily stay again."
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC
Property grounds

Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC

10.0 out of 10, Exceptional, (2)
"Great, cozy, quiet little spot! Perfect for 4 adults and a baby. My 1.5 year old loved exploring the deck with an amazing water view, and gained lots of confidence navigating the little steps throughout the house and worked on her balance. Kitchen was well appointed and suited our needs. Would stay here again!"
Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC
Thunder Hill Retreat - Spacious/Deck/Hot tub
Outdoor spa tub

Thunder Hill Retreat - Spacious/Deck/Hot tub

10.0 out of 10, Exceptional, (13)
"Had a nice stay."
$490 nightly
The price is $542
Jun 30 - Jul 1
Total includes taxes and fees
Thunder Hill Retreat - Spacious/Deck/Hot tub
Private Carriage House Retreat on a 33 Acre Historic Working Estate
Exterior

Private Carriage House Retreat on a 33 Acre Historic Working Estate

10.0 out of 10, Exceptional, (11)
"Place was great !"
Private Carriage House Retreat on a 33 Acre Historic Working Estate
Waterfront Cottage on the C&D Canal!
Fridge, microwave, oven, stovetop

Waterfront Cottage on the C&D Canal!

8.0 out of 10, Very Good, (5)
"Fantastic location "
Waterfront Cottage on the C&D Canal!
Quarry Landing - Center of Town & River View - 3 Bedroom
Property grounds

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

9.8 out of 10, Exceptional, (7)
"Great stay in a relaxing community. We loved to be able to walk to places from the house! The hosts were very helpful and easy to communicate with 💙"
$329 nightly
The price is $349
Jun 29 - Jun 30
Total includes taxes and fees
Quarry Landing - Center of Town & River View - 3 Bedroom
A cottage on the shore of the Delaware River
On the beach

A cottage on the shore of the Delaware River

9.8 out of 10, Exceptional, (61)
"The coziest house we have ever stayed at ! The host went above and beyond to have everything we could need! Would definitely recommend ! "
A cottage on the shore of the Delaware River
Waterfront cottage in historic Charlestown, Maryland
Interior

Waterfront cottage in historic Charlestown, Maryland

9.8 out of 10, Exceptional, (7)
"Such a charming property and town. We loved everything about it!"
Waterfront cottage in historic Charlestown, Maryland
Be persuaded to experience this vintage cottage by the Sassa
Outdoor dining

Be persuaded to experience this vintage cottage by the Sassa

9.4 out of 10, Exceptional, (8)
"Had a lovely peaceful stay. Great amenities."
Be persuaded to experience this vintage cottage by the Sassa
Waterfront Historical District Home Near River
House (3 Bedrooms) | Interior

Waterfront Historical District Home Near River

3.0 star property
10.0 out of 10, Exceptional, (1)
"The home was beautiful and well kept. Essential kitchen items are included along with sheets and towels. Dawn was a super reliable host. Communication was wonderful. She had toiletries and some stocked snacks for the guests. Although we did not have time to use them, there were cornhole boards and ladder ball for guests to use. The home is about a block to the river where fishing is a must. There is also a public beach within walking distance. I would recommend this house to anyone looking for...
Waterfront Historical District Home Near River
Charming 2-bedroom water oriented cottage with water access
Marina

Charming 2-bedroom water oriented cottage with water access

10.0 out of 10, Exceptional, (1)
"This adorable cottage provided the perfect atmosphere for a week long getaway. The kitchen was immaculate and the center island quickly became our favorite place to sip our morning coffee. The bathroom was roomy with a beautiful shower and a large washer and dryer.The host was gracious and left cookies and candy as well as beautiful flowers upon our arrival. If our family is ever visiting the area again, we will definitely stay here!"
Charming 2-bedroom water oriented cottage with water access
3 Mi to Dover Motor Speedway: Pet-friendly Retreat
Interior

3 Mi to Dover Motor Speedway: Pet-friendly Retreat

3.0 star property
3 Mi to Dover Motor Speedway: Pet-friendly Retreat
Vintage Waterfront Cottage with Stunning Sunsets
Terrace/patio

Vintage Waterfront Cottage with Stunning Sunsets

10.0 out of 10, Exceptional, (5)
"This was a perfect spot for a quick getaway for my husband and I! The house is lovely with plenty of charm, a well-appointed kitchen and comfortable furniture. The yard is lovely and it’s just a short walk to the private beach to bird watch or just take a stroll. Would highly recommend!"
Vintage Waterfront Cottage with Stunning Sunsets
Long Beach Cottage, (romantic couple’s getaway)
Property grounds

Long Beach Cottage, (romantic couple’s getaway)

10.0 out of 10, Exceptional, (4)
"Loved the property and the decor. Very well done and luxurious!"
$722 nightly
The price is $759
Jul 17 - Jul 18
Total includes taxes and fees
Long Beach Cottage, (romantic couple’s getaway)
Family-Friendly Cottage, Walk to the Beach!
Interior

Family-Friendly Cottage, Walk to the Beach!

10.0 out of 10, Exceptional, (18)
"Great location "
Family-Friendly Cottage, Walk to the Beach!
Grandma’s Cottage will wrap around you like a warm hug
Terrace/patio

Grandma’s Cottage will wrap around you like a warm hug

$339 nightly
The price is $359
Jun 26 - Jun 27
Total includes taxes and fees
Grandma’s Cottage will wrap around you like a warm hug
3 Mi to Dtwn: Home w/ Yard in Newark
Interior

3 Mi to Dtwn: Home w/ Yard in Newark

3.0 star property
3 Mi to Dtwn: Home w/ Yard in Newark
Family-friendly Cottage, Walk to the Beach!
Interior

Family-friendly Cottage, Walk to the Beach!

3.0 star property
Family-friendly Cottage, Walk to the Beach!
Spacious North East Home w/ Fenced Yard & Fire Pit
Interior

Spacious North East Home w/ Fenced Yard & Fire Pit

3.0 star property
Spacious North East Home w/ Fenced Yard & Fire Pit
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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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.