Title: Where to Stay in Chestertown: Best neighborhoods | Expedia.com

[Hotels in Chestertown](https://expedia.com/Chestertown-Hotels.d7215.Travel-Guide-Hotels)[Vacation Rentals in Chestertown](https://expedia.com/Chestertown-Vacation-Rentals.d7215.Travel-Guide-VacationRentals)[Flights to Chestertown](https://expedia.com/Cheap-Flights-To-Chestertown.d7215.Travel-Guide-Flights)[Car Rentals in Chestertown](https://expedia.com/Car-Rentals-In-Chestertown.d7215.Car-Rental-Guide)[Chestertown Vacation Packages](https://expedia.com/Chestertown.d7215.Destination-Travel-Guides)

# Where to stay

## in Chestertown

## Visit Chestertown

Best places to stay for families

Best places to stay with pools

[Chestertown Travel Guide](https://expedia.com/Chestertown.dx7215)

## Quaint Chestertown awaits: its sports, university life, wildlife, and more! 

Venture to sights like Historical Society of Kent County Maryland and Rolphs Wharf Marina as you discover Chestertown—a city also notable for its college vibe.

![Aerial summer view of colonial Chestertown on the Chesapeake Bay in Maryland USA](https://images.trvl-media.com/place/7215/2810851e-b7cc-4dfb-bf7e-dc0611ab1b49.jpg)

![Aerial summer view of colonial Chestertown on the Chesapeake Bay in Maryland USA](https://images.trvl-media.com/place/7215/2127ed08-151b-4865-9870-3d0463a3d88b.jpg)

![Eastern Shore Maryland, USA is between the Chesapeake bay and Delaware Bay. There are so many farms and fresh produce in this area just 20 minutes from the surrounding water ways. There are also small venues to eat and all have great crabs and crab bisque.](https://images.trvl-media.com/place/7215/6507b0e9-7981-44e0-9a0d-e95b6eb38908.jpg)

![Eastern Shore small towns in Maryland, USA. Traveling the Eastern Shore points o f Maryland this weekend, we came across this local church with gravestones. We found several of these local churches along with the many farms and inlets leading to the Chesapeake bay.](https://images.trvl-media.com/place/7215/39d32fed-717d-4f49-ae4c-a7eb875f5cb2.jpg)

![Somewhere over the rainbow... Terrific view on the plane back to the North. ](https://images.trvl-media.com/place/7215/bcea7b39-67dd-4c9c-ac85-acb331a5426e.jpg)

## Best places to stay for families

[Comfort Inn & Suites Chestertown](https://www.expedia.com/Chestertown-Hotels-Comfort-Inn-Suites.h1700736.Hotel-Information) is a hotel featuring free parking and free full breakfast that guests like for its helpful staff and clean rooms. [Red Roof Inn & Suites Chestertown](https://www.expedia.com/Chestertown-Hotels-Red-Roof-Inn-Suites-Chestertown.h40352.Hotel-Information) is a hotel featuring free parking and laundry facilities that guests like for its helpful staff. 

#### Recommended hotels

## Best places to stay with pools

[The Lodge at Great Oak Landing](https://www.expedia.com/Chestertown-Hotels-The-Lodge-At-Great-Oak-Landing.h96826266.Hotel-Information) is a lodge featuring a seasonal outdoor pool and a golf course. You'll also be close to Chesapeake Bay and Northern Chesapeake Bay. 

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