Photo by Michelle Gonzalez

Search Cottages in Middletown

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Check prices for these dates

Next weekend
9 Jum. I - 11 Jum. I
In two weeks
16 Jum. I - 18 Jum. I
In one month
30 Jum. I - 1 Jum. II
In two months
27 Jum. II - 29 Jum. II

Compare 29 Cottages in Middletown with updated reviews, rates, and availability.

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, (60)
"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
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Beach nearby, sun loungers

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

9.8 out of 10, Exceptional, (47)
"We really enjoyed the water views & walking by the water. It was a very enjoyable and relaxing stay."
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
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
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 💙"
The price is SAR 806
SAR 1,157 total
includes taxes & fees
19 May - 20 May
Quarry Landing - Center of Town & River View - 3 Bedroom
Chesapeake Romantic Waterfront Home with Private Pool
Interior

Chesapeake Romantic Waterfront Home with Private Pool

8.8 out of 10, Excellent, (5)
"Great communication, easy to access, accommodations true to listing. Spacious, renovated living space. Great outdoor pool."
Chesapeake Romantic Waterfront Home with Private Pool
Thunder Hill Retreat - Spacious/Deck/Hot tub
Outdoor spa tub

Thunder Hill Retreat - Spacious/Deck/Hot tub

10.0 out of 10, Exceptional, (12)
"Had a nice stay."
The price is SAR 788
SAR 1,812 total
includes taxes & fees
5 May - 6 May
Thunder Hill Retreat - Spacious/Deck/Hot tub
Sunset River Shack - Waterfront Boho Cottage on the Elk River /Chesapeake Bay
Terrace/patio

Sunset River Shack - Waterfront Boho Cottage on the Elk River /Chesapeake Bay

2.0 star property
9.0 out of 10, Wonderful, (2)
"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 - Waterfront Boho Cottage on the Elk River /Chesapeake Bay
Waterfront cottage in historic Charlestown, Maryland
Interior

Waterfront cottage in historic Charlestown, Maryland

9.6 out of 10, Exceptional, (5)
"Such a charming property and town. We loved everything about it!"
Waterfront cottage in historic Charlestown, Maryland
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
Charming 2-bedroom water oriented cottage with water access
Fridge, microwave, oven, stovetop

Charming 2-bedroom water oriented cottage with water access

Charming 2-bedroom water oriented cottage with water access
Vintage Waterfront Cottage with Stunning Sunsets
Beach nearby, sun loungers, beach towels

Vintage Waterfront Cottage with Stunning Sunsets

10.0 out of 10, Exceptional, (5)
"thoroughly enjoyed our time at this lovely property. the quiet location, attention to detail, and communication with owners all made for an delightful stay. "
Vintage Waterfront Cottage with Stunning Sunsets
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!
Long Beach Cottage, (romantic couple’s getaway)
Property grounds

Long Beach Cottage, (romantic couple’s getaway)

10.0 out of 10, Exceptional, (3)
"Loved the property and the decor. Very well done and luxurious!"
The price is SAR 1,218
SAR 1,897 total
includes taxes & fees
8 May - 9 May
Long Beach Cottage, (romantic couple’s getaway)
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
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!
Waterfront Historical District Home Near River
House (3 Bedrooms) | Private kitchen | Microwave, oven, stovetop, dishwasher

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
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
Wilmington Home ~ 28 Mi to Downtown Philadelphia!
Interior

Wilmington Home ~ 28 Mi to Downtown Philadelphia!

3.0 star property
Wilmington Home ~ 28 Mi to Downtown Philadelphia!
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
Waterfront Millington Vacation Rental w/ Hot Tub!
House (Multiple Bedrooms) | Interior

Waterfront Millington Vacation Rental w/ Hot Tub!

3.0 star property
Waterfront Millington Vacation Rental w/ 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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Other property types in Middletown

Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck
Fridge, microwave, oven, stovetop

Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck

9.0 out of 10, Wonderful, (2)
"Nice and quiet place to stay"
The price is SAR 506
SAR 1,053 total
includes taxes & fees
6 May - 7 May
Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck
Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.
Property grounds

Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.

9.6 out of 10, Exceptional, (24)
"Decided to try something different, and luckily found the Dockside Doghouse. Very comfortable, incredibly relaxing."
Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.
Captivating Chesapeake experience
Beach

Captivating Chesapeake experience

10.0 out of 10, Exceptional, (259)
"Such a hidden gem of a spot! Pictures were exactly like the house and the owners were super responsive!"
Captivating Chesapeake experience
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.