Middletown Cottages

Get more for your budget and save up to 50% off select Secret Bargain hotels

Get even more value with CheapTickets Price Guarantee!

Change your flight without a fee on select flights

Cottages in Middletown

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

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 Chesland Park and Brantwood Park.

Pool

Kitchen

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

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

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 North East Community Park.

Kitchen

Washer

Waterfront Cottage on the C&D Canal!

Chesapeake City MD

When you 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

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

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

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

$218 nightly

$231 total

Nov 11 - Nov 12

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

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

Don't see what you're looking for?

See all available properties in Middletown

View all properties

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.