Book Guest Houses in Chestertown, MD

Top Guest Houses in Chestertown

Island Life! Kent Island Waterfront with Pool-Bring your boat!

This guesthouse features an outdoor pool and a hot tub. A garden, laundry facilities, and barbecue grills are also on offer.

Pool

Hot Tub

Calico Cottage Guest House

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This guesthouse includes a garden and laundry facilities.

Air conditioning

Parking available

Top Floor Handicap Accessible Bay View

60 Sandy Cove Road, North East, MD

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A marina and an outdoor pool are featured at this smoke-free guesthouse. Enjoy the gym and perks like free self parking. A convenience store is also provided.

Pool

Parking included

Top Floor East Handicap Accessible

60 Sandy Cove Road, North East, MD

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A marina and an outdoor pool are featured at this smoke-free guesthouse. Enjoy the gym and perks like free self parking. A convenience store is also provided.

Pool

Parking included

Top Floor Family Deluxe Bay View

60 Sandy Cove Road, North East, MD

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A marina and an outdoor pool are featured at this smoke-free guesthouse. Enjoy the gym and perks like free self parking. A convenience store is also provided.

Pool

Parking included

Second Floor Standard Deluxe Bay View

60 Sandy Cove Road, North East, MD

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A marina and an outdoor pool are featured at this smoke-free guesthouse. Enjoy the gym and perks like free self parking. A convenience store is also provided.

Pool

Parking included

Top Floor Standard Suite

60 Sandy Cove Road, North East, MD

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A marina and an outdoor pool are featured at this smoke-free guesthouse. Enjoy the gym and perks like free self parking. A convenience store is also provided.

Pool

Parking included

Second Floor Standard Suite Bay View

60 Sandy Cove Road, North East, MD

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A marina and an outdoor pool are featured at this smoke-free guesthouse. Enjoy the gym and perks like free self parking. A convenience store is also provided.

Pool

Parking included

Second Floor East Standard Deluxe

60 Sandy Cove Road, North East, MD

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A marina and an outdoor pool are featured at this smoke-free guesthouse. Enjoy the gym and perks like free self parking. A convenience store is also provided.

Pool

Parking included

Top Floor Standard Deluxe

60 Sandy Cove Road, North East, MD

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A marina and an outdoor pool are featured at this smoke-free guesthouse. Enjoy the gym and perks like free self parking. A convenience store is also provided.

Pool

Parking included

Second Floor Family Deluxe

60 Sandy Cove Road, North East, MD

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A marina and an outdoor pool are featured at this smoke-free guesthouse. Enjoy the gym and perks like free self parking. A convenience store is also provided.

Pool

Parking included

First Floor Family Deluxe Suite

60 Sandy Cove Road, North East, MD

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A marina and an outdoor pool are featured at this smoke-free guesthouse. Enjoy the gym and perks like free self parking. A convenience store is also provided.

Pool

Parking included

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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.

Top hotels in Chestertown

Sagamore Pendry Baltimore

1715 Thames St., Baltimore, MD

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9.4/10 Exceptional! (1,003 reviews)

Chestertown Guest Houses essential information

Accommodation	17 Guest Houses
Lowest Price
Highest Price
Popular accommodation	Island Life! Kent Island Waterfront with Pool-Bring your boat!, Calico Cottage Guest House, Top Floor Handicap Accessible Bay View, Top Floor East Handicap Accessible, Top Floor Family Deluxe Bay View, Second Floor Standard Deluxe Bay View, Top Floor Standard Suite, Second Floor Standard Suite Bay View, Second Floor East Standard Deluxe, Top Floor Standard Deluxe, Second Floor Family Deluxe, First Floor Family Deluxe Suite