Middletown Cottages

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Cottages in Middletown

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

Elkton MD

Located in Elkton, this cottage is on the waterfront, a 5-minute drive from Chesland Park and 6 minutes from Brantwood Park.

Kitchen

Washer

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

Port Deposit MD

$200 nightly

$212 total

Jan 26 - Jan 27

Total with taxes and fees

A stay at this cottage places you in the heart of Port Deposit, a 1-minute drive from Susquehanna River and 6 minutes from Hollywood Casino.

Kitchen

Washer

Chesapeake City Pool Retreat – Waterfront Stay in the Woods

Elkton MD

With a stay at this cottage in Elkton, you'll be within a 10-minute drive of Brantwood Park and Chesapeake City Bridge.

Pool

Kitchen

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

Earleville MD

Located in Earleville, this cottage is in a rural location, within a 15-minute drive of Earleville Wildlife Management Area and Earleville Wildlife Management Area.

Kitchen

Washer

Eastern shore beachfront cottage with stunning sunset views!

Worton MD

Located in Worton, this cottage is on the waterfront, within a 10-minute drive of Betterton Community Park and Betterton Historic District.

Be persuaded to experience this vintage cottage by the Sassa

Galena MD

Located in Galena, this cottage is on a river, within a 10-minute drive of Galena Town Hall and Galena Town Park.

Kitchen

Washer

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

North East MD

Located in North East, this cottage is a 2-minute drive from Upper Bay Museum and 5 minutes from Milburn Stone Theater.

Kitchen

Parking included

Waterfront Cottage on the C&D Canal!

Chesapeake City MD

When you a stay at this cottage in Chesapeake City, you'll be on the waterfront, just steps from Chesapeake Inn Marina and Chesapeake City Town Hall.

Kitchen

Free WiFi

Charming 2-bedroom water oriented cottage with water access

North East MD

Located in North East, this cottage is on a river, a 4-minute drive from Upper Bay Museum and 9 minutes from Roachs Shore.

Kitchen

Washer

Thunder Hill Retreat - Spacious/Deck/Hot tub

Lincoln University PA

$404 nightly

$446 total

Jan 21 - Jan 22

Total with taxes and fees

This cottage is 11.1 mi (17.9 km) from University of Delaware and 3.9 mi (6.3 km) from Lower Chrome Serpentine Barrens.

Waterfront Historical District Home Near River

Charlestown MD

With a stay at this cottage in Charlestown, you'll be within a 5-minute walk of Long Point Park and Fair Green Park.

3 Mi to Dover Motor Speedway: Pet-friendly Retreat

Dover DE

With a stay at this cottage in Dover, you'll be within a 10-minute drive of Dover International Speedway and Greentree Village Shopping Center.

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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.