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Search Guest Houses in Chestertown

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Calico Cottage Guest House

10.0 out of 10, Exceptional, (8)
"This tiny house is tastefully furnished and, coupled with the quiet neighborhood, provides a relaxing, peaceful environment."
Calico Cottage Guest House

Top Floor East Handicap Accessible

2.0 star property
Top Floor East Handicap Accessible

Center Parlor Room at Sandy Cove

2.5 star property
Center Parlor Room at Sandy Cove

Second Floor Standard Deluxe Bay View

2.0 star property
Second Floor Standard Deluxe Bay View

Second Floor East Standard Deluxe

2.0 star property
Second Floor East Standard Deluxe

Second Floor Standard Suite Bay View

2.0 star property
Second Floor Standard Suite Bay View

First Floor Bay View Deluxe Suite

2.0 star property
First Floor Bay View Deluxe Suite

Top Floor Handicap Accessible Bay View

2.0 star property
Top Floor Handicap Accessible Bay View

Top Floor Standard Suite

2.0 star property
Top Floor Standard Suite

Second Floor Family Deluxe

2.0 star property
Second Floor Family Deluxe

First Floor Family Deluxe Suite

2.5 star property
First Floor Family Deluxe Suite

Top Floor Standard Deluxe

2.5 star property
Top Floor Standard Deluxe

Top Floor Deluxe Suite Bay View

2.5 star property
Top Floor Deluxe Suite Bay View

Top Floor Family Deluxe Bay View

2.0 star property
Top Floor Family Deluxe Bay View

Top Floor Family Deluxe

2.5 star property
Top Floor Family Deluxe
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.
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Other property types in Chestertown

350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock

10.0 out of 10, Exceptional, (61)
"Great!"
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

10.0 out of 10, Exceptional, (202)
"This cozy home was perfect for my coaches & I that were in town for a lacrosse tourney @ the Naval Academy. This home is literally less than 100 steps from the gate of the Naval Base and same distance to dowtown Annapolis city docks, diming, shopping and sight-seeing. We will defintely be back! Thanks John!!"
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

10.0 out of 10, Exceptional, (20)
"Our group had an amazing time staying on this property. There are many areas inside the house as well as outside the house where you can gather with family and friends. It was very quick and easy to order Ubers/lyfts to the downtow Annapolis area whenever we needed. The house is also convientely located near a small shaping center less than a mile away. We would highly recommend this property!"
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
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.
Beautiful view of the beach with palm trees

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