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In two weeks
Oct 10 - Oct 12
In two months
Nov 21 - Nov 23
In three months
Dec 19 - Dec 21
In four months
Jan 16 - Jan 18

Cottages in Middletown

Thunder Hill Retreat - Spacious/Deck/Hot tub
Outdoor spa tub

Thunder Hill Retreat - Spacious/Deck/Hot tub

10.0 out of 10, Exceptional, (14)
"Our stay was perfect! We had a wonderful time with family celebrating our daughter's UD graduation."
$447 nightly
The price is $493
Oct 9 - Oct 10
Total with taxes and fees
Thunder Hill Retreat - Spacious/Deck/Hot tub
Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC
Outdoor dining

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

10.0 out of 10, Exceptional, (9)
"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
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, (9)
"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 💙"
$230 nightly
The price is $244
Oct 13 - Oct 14
Total with taxes and fees
Quarry Landing - Center of Town & River View - 3 Bedroom
Chesapeake City Pool Retreat – Waterfront Stay in the Woods
Terrace/patio

Chesapeake City Pool Retreat – Waterfront Stay in the Woods

9.2 out of 10, Wonderful, (12)
"Great location right on the water. Great for fishing or just sitting and relaxing. The house is in a quiet secluded area but only 10 minutes from Chesapeake Bay. Pool was an awesome extra. My son enjoyed it. The home was clean and plenty of space. "
Chesapeake City Pool Retreat – Waterfront Stay in the Woods
Cozy Cottage on the North East River in Town!
Exterior

Cozy Cottage on the North East River in Town!

10.0 out of 10, Exceptional, (1)
"Super clean, great location, host communication was top tier, house was fully stocked, and bird watching by the river was fantastic "
Cozy Cottage on the North East River in Town!
Sunset River Shack -amazing waterfront view
Property grounds

Sunset River Shack -amazing waterfront view

2.0 star property
9.4 out of 10, Exceptional, (3)
"The home is nice The view from the deck was wonderful But there wasn’t access to the water Easy to find and we really enjoyed the area"
Sunset River Shack -amazing waterfront view
Waterfront cottage in historic Charlestown, Maryland
Exterior

Waterfront cottage in historic Charlestown, Maryland

9.8 out of 10, Exceptional, (10)
"Such a charming property and town. We loved everything about it!"
Waterfront cottage in historic Charlestown, Maryland
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Outdoor dining

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

9.8 out of 10, Exceptional, (57)
"Lovely cottage, well-equipped, immaculately clean. "
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Eastern shore beachfront cottage with stunning sunset views!
Interior

Eastern shore beachfront cottage with stunning sunset views!

10.0 out of 10, Exceptional, (2)
"Our family had a great time at the cottage. It is very well appointed and a great place to connect with family. They kayaks were fun to use and we caught a catfish right from the bank. "
Eastern shore beachfront cottage with stunning sunset views!
A cottage on the shore of the Delaware River
Exterior

A cottage on the shore of the Delaware River

9.8 out of 10, Exceptional, (65)
"This small home was perfect for a stay on our road trip. Beautiful views and quiet place to stay."
A cottage on the shore of the Delaware River
Waterfront Cottage on the C&D Canal!
Exterior

Waterfront Cottage on the C&D Canal!

8.0 out of 10, Very Good, (5)
"Fantastic location "
Waterfront Cottage on the C&D Canal!
Walk to Town & River: Charming Home in North East!
House (3 Bedrooms) | Interior

Walk to Town & River: Charming Home in North East!

3.0 star property
Walk to Town & River: Charming Home in North East!
3 Mi to Dover Motor Speedway: Pet-friendly Retreat
House (3 Bedrooms) | Interior

3 Mi to Dover Motor Speedway: Pet-friendly Retreat

3.0 star property
3 Mi to Dover Motor Speedway: Pet-friendly Retreat
Charming 2-bedroom water oriented cottage with water access
Exterior

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
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, (2)
"The home was beautiful and well kept. Essential kitchen items are included along with sheets and towels. The host was a super reliable. Communication was wonderful. The host had toiletries and some stocked snacks for the guests. There were corn hole 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. "
Waterfront Historical District Home Near River
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!"
$479 nightly
The price is $502
Oct 6 - Oct 7
Total with taxes and fees
Long Beach Cottage, (romantic couple’s getaway)
Be persuaded to experience this vintage cottage by the Sassa
Outdoor dining

Be persuaded to experience this vintage cottage by the Sassa

9.2 out of 10, Wonderful, (10)
"Had a lovely peaceful stay. Great amenities."
Be persuaded to experience this vintage cottage by the Sassa
Grandma’s Cottage will wrap around you like a warm hug
Exterior

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

$388 nightly
The price is $411
Sep 28 - Sep 29
Total with taxes and fees
Grandma’s Cottage will wrap around you like a warm hug
Outdoor Oasis + Hot Tub: Maryland Home w/ Bar!
House (3 Bedrooms) | Interior

Outdoor Oasis + Hot Tub: Maryland Home w/ Bar!

3.0 star property
Outdoor Oasis + Hot Tub: Maryland Home w/ Bar!
3 Mi to Dtwn: Home w/ Yard in Newark
House (3 Bedrooms) | Interior

3 Mi to Dtwn: Home w/ Yard in Newark

3.0 star property
3 Mi to Dtwn: Home w/ Yard in Newark
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

Bally's Dover Casino Resort

Bally's Dover Casino Resort

10/10 Excellent
"Short n sweet & a good nights sleep"
Alta 1-night trip
Posted 2 days ago
Bally's Dover Casino Resort

Find out more about Middletown

Find out more about Middletown

Middletown Cottages information

Number of reviews
197
Accommodation
32 Cottages
Lowest Price
$244
Highest Price
$502

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