Photo by Michelle Gonzalez

Search Cottages in Middletown

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Compare 23 Cottages in Middletown with updated reviews, rates, and availability.

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

9.8 out of 10, Exceptional, (45)
"Great little home away from home. A small orientation list for newcomers would be helpful. Closest groceries, gas and such. Outside of that all and all VERY pleasing. "
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

A cottage on the shore of the Delaware River

9.8 out of 10, Exceptional, (59)
"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

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

9.8 out of 10, Exceptional, (7)
"On a small hillside. Very quaint accommodation. Close to restaurants and river. Parking a little difficult to figure out, train is a bit loud and frequent but everything else was as advertised and nice. "
The price is SAR 555
SAR 855 total
includes taxes & fees
11 Mar - 12 Mar
Quarry Landing - Center of Town & River View - 3 Bedroom

Thunder Hill Retreat - Spacious/Deck/Hot tub

10.0 out of 10, Exceptional, (11)
"Had a nice stay."
The price is SAR 788
SAR 1,848 total
includes taxes & fees
11 Mar - 12 Mar
Thunder Hill Retreat - Spacious/Deck/Hot tub

Waterfront cottage in historic Charlestown, Maryland

9.6 out of 10, Exceptional, (5)
"Our stay was amazing! Extremely cute and clean cottage. Water view was beautiful. Very relaxing weekend. Great communication with host. Can’t wait to go back. "
Waterfront cottage in historic Charlestown, Maryland

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

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

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

Be persuaded to experience this vintage cottage by the Sassa

9.4 out of 10, Exceptional, (8)
"We had one of the best vacations ever. Our 9 and 7 year old grandchildren wanted to live there forever! We had a beautiful house and access to the outdoor spaces including a dock for gishing, crabbing and swimming. We were able to make smores over a great fire pit and enjoyed phenominal sunsets from a sitting area overlooking the river. Gene and Suzie, the hosts were on-site and so warm and welcoming. Our every need was met immediately. We will definitely be vacationing at Gregg Neck Cottage...
Be persuaded to experience this vintage cottage by the Sassa

Elsinboro Retreat I 3BR I 2BA I - enjoy fishing , hunting, jet skiing,& hiking.

8.8 out of 10, Excellent, (3)
"Enjoyed our stay. House was perfect for the 2 of us. Definitely better than staying in a noisy hotel!"
Elsinboro Retreat I 3BR I 2BA I - enjoy fishing , hunting, jet skiing,& hiking.

Long Beach Cottage, (romantic couple’s getaway)

10.0 out of 10, Exceptional, (3)
"We had a wonderful time! Being near the water is my happy place. The size of the home is perfect for me. And the weather was perfect! Thank you!"
The price is SAR 1,086
SAR 1,755 total
includes taxes & fees
13 Mar - 14 Mar
Long Beach Cottage, (romantic couple’s getaway)

Adorable 100-year-old tiny home in historic town. Gym membership included!

10.0 out of 10, Exceptional, (1)
Adorable 100-year-old tiny home in historic town. Gym membership included!

Waterfront Cottage on the C&D Canal!

8.0 out of 10, Very Good, (5)
"Fantastic location "
Waterfront Cottage on the C&D Canal!

Charming 2-bedroom water oriented cottage with water access

Charming 2-bedroom water oriented cottage with water access

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

Family-Friendly Cottage, Walk to the Beach!

10.0 out of 10, Exceptional, (18)
"Another amazing stay at Robin’s Rest. Highly recommend for a quiet weekend getaway "
Family-Friendly Cottage, Walk to the Beach!

Waterfront Historical District Home Near River

3.0 star property
Waterfront Historical District Home Near River

3 Mi to Dover Motor Speedway: Pet-friendly Retreat

3.0 star property
3 Mi to Dover Motor Speedway: Pet-friendly Retreat

Wilmington Home ~ 28 Mi to Downtown Philadelphia!

3.0 star property
Wilmington Home ~ 28 Mi to Downtown Philadelphia!

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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Other property types in Middletown

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

9.4 out of 10, Exceptional, (22)
"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.

Charming 2-bedroom house with WiFi, AC in marvelous Wilmington

Charming 2-bedroom house with WiFi, AC in marvelous Wilmington

Cozy on the Hill. Close to Riverfront, Brandywine park and great food

9.8 out of 10, Exceptional, (9)
"It was fine"
Cozy on the Hill. Close to Riverfront, Brandywine park and great food
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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