Middletown Cottages

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Cottages in Middletown

Charming 2-bedroom cottage at Murphy's Beach in lovely Charlestown Maryland

Charlestown MD

With a stay at this cottage in Perryville, you'll be within a 15-minute walk of Charlestown Town Hall and Fair Green Park.

Kitchen

Washer

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

Earleville MD

With a stay at this cottage in Earleville, you'll be near the beach, within a 15-minute drive of Chesapeake Bay and Earleville Wildlife Management Area.

Kitchen

Washer

Charming Cottage - Northeast River / Chesapeake Bay

Perryville MD

With a stay at this cottage in Perryville, you'll be within a 5-minute drive of Chesapeake Bay and Chestnut Point Estates and Marina.

Kitchen

Washer

Waterfront Home, Private Dock, A/C, Amazing Views, Boating, Fishing & Kayaking

North East MD

With a stay at this cottage in North East, you'll be on the waterfront, within a 15-minute drive of Chesapeake Bay and Upper Bay Museum.

Kitchen

Washer

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

Charming 2-bedroom water oriented cottage with water access

North East MD

With a stay at this cottage in North East, you'll be on a river, within a 15-minute drive of Chesapeake Bay and Chesapeake Bay Golf Club.

Kitchen

Washer

Life is better at the RIVER!--Cozy waterfront cottage

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

Free WiFi

Eastern shore beachfront cottage with stunning sunset views!

Worton MD

With a stay at this cottage in Worton, you'll be on the beach, within a 15-minute drive of Chesapeake Bay and Betterton Community Park.

Kitchen

Washer

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

Port Deposit MD

$291 nightly

$308 total

Sep 1 - Sep 2

Total with taxes and fees

A stay at this cottage places you in the heart of Port Deposit, within a 10-minute walk of Community Connecting - Labyrinth and Susquehanna River.

Kitchen

Washer

Waterfront cottage in historic Charlestown, Maryland

Charlestown MD

With a stay at this cottage in Charlestown, you'll be just steps from Fair Green Park and Charlestown Town Hall.

Kitchen

Washer

Chesapeake City Pool Retreat – Waterfront Stay in the Woods

Elkton MD

Located in Elkton, this cottage is within a 15-minute drive of Chesapeake City Bridge and Elk Forest Wildlife Management Area.

Pool

Kitchen

Long Beach Cottage, (romantic couple’s getaway)

Charlestown MD

Located in Perryville, this cottage is on the waterfront, within a 15-minute walk of Charlestown Town Hall and Fair Green Park.

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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.