Chestertown Cottages from CA $425

An aerial view of a town with a river, buildings, and surrounding greenery.

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Our top choices for Chestertown cottages

A two-story house with a wooden deck, a garage, and a shed in the backyard.

1. Lakefront Home Firepit BWI Marleycreek River

Marley

CA $425 total

includes taxes & fees

Sep 9 - Sep 10

A wooden deck with wicker furniture, a round table, and a fire pit.

2. Chesapeake Cottages- 2 Quaint Waterfront Retreats

Pasadena

Buu T.

CA $917 total

includes taxes & fees

Sep 8 - Sep 9

A marina with multiple sailboats docked.

3. Secluded Cozy Cottage in Historic Downtown

Historic District

Tim G.

CA $1,033 total

includes taxes & fees

Sep 8 - Sep 9

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Top Chestertown Hotel Reviews

Best Western Kent Narrows Inn

8/10 Good

"A little out of date"

Historic Inns of Annapolis

8/10 Good

"I liked the archaeological displays and the historically preserved property. The room was very comfortable. Some of the front desk staff were not very friendly. Some of the parking attendants were often seen glued to their cell phones rather than offering assistance. The valet online service was inconvenient and too expensive. I wanted to leave an online gratuity but did not like the convenience fee charged!"

Best Western Plus Hotel & Conference Center

10/10 Excellent

"Multiple Elevators were out of service and had longer wait for available one to use. Buttons seemed to not work in that one elevator that was working and light kept going out for the floor I needed to be and kept stopping one floor below instead. But staff were so kind and friendly. Very helpful staff with information in area, shuttle information and very welcoming. I did enjoy staying and if coming to Baltimore again, I will choose to stay here again. Hope the elevator will be in good condition by the time I go back."

Hampton Inn Baltimore/Glen Burnie

8/10 Good

"Only one elevator working and it was the slowest elevator ever, especially since there is only 5 floors! The lobby is bright and welcoming, but the room, while clean, had dark furniture and dark carpeting and are generally just not very bright and cheery. We have stayed here before and had no issues either the room but this time the air conditioner seemed to blow bad smelling air. It might have been due to the standing water on the flat roof outside our window."

The Lodge at Great Oak Landing

10/10 Excellent

"Gem of a local place on the water. The rooms are big and the beds are soooo comfy. The pool is cute and the beach has bands on weekends. There are gas grills and a decent restaurant. It's not fancy (for fancy stay at the manor next door). But it's not corporate either. It's authentic, peaceful and fun."

Find out more about Chestertown

Chestertown Cottages information

Number of reviews	22
Accommodation	63 Cottages
Lowest Price	CA $425
Highest Price	CA $1,033

Frequently asked questions

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What is there to do in Chestertown near my cottage?

If you'd like to fill up your itinerary in Chestertown, find your way to Rolphs Wharf Marina. It's a winner with locals and tourists alike.

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Stevensville Vacation Rentals

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Room 1

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Treat yourself

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Check prices for these dates

Our top choices for Chestertown cottages

1. Lakefront Home Firepit BWI Marleycreek River

2. Chesapeake Cottages- 2 Quaint Waterfront Retreats

3. Secluded Cozy Cottage in Historic Downtown

Find vacation rentals that suit your style

Top Chestertown Hotel Reviews

Best Western Kent Narrows Inn

Hyatt Place Kent Narrows & Marina

Historic Inns of Annapolis

Best Western Plus Hotel & Conference Center

Hampton Inn Baltimore/White Marsh

Hampton Inn Baltimore/Glen Burnie

The Lodge at Great Oak Landing

Find out more about Chestertown

Chestertown Cottages information

Frequently asked questions

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Search Chestertown Cottage Rentals from CA $425

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Chestertown cottages

1. Lakefront Home Firepit BWI Marleycreek River

2. Chesapeake Cottages- 2 Quaint Waterfront Retreats

3. Secluded Cozy Cottage in Historic Downtown

Find vacation rentals that suit your style

Top Chestertown Hotel Reviews

Best Western Kent Narrows Inn

Find out more about Chestertown

Chestertown Cottages information

Frequently asked questions

Explore a world of travel with Expedia