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Vacation Rentals in Chestertown, Maryland

about Chestertown

We feature rental homes, villas, cabins, cottages, and condos in destinations all over the world. If you're looking for Chestertown, Maryland vacation rentals, click the "rental results" tab and inquire about your favorite listings. Browse Chestertown vacation deals, family-friendly amenities, and more. If you can't find what you're looking for, remember that vacation rentals in Chestertown, Maryland are added and updated every week, so please bookmark us and come back for a visit! Feel free to peruse other destinations as well, as we've got everything from large family vacation rentals to lake cabins to luxury beach houses.

Chestertown, Maryland Vacation Rentals and Tourism

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Chestertown things to do

 

The Prince Theatre

A lovely and lovingly-restored historic theater in quaint but still thriving Chestertown Maryland. While tourism seems to keep part of the Eastern Shore...read more

 

Carla Massoni Fine Art Gallery

This is a nice, fairly laid back gallery in the nice (i.e. historic part of town). Ms. Massoni was more than happy to talk about her hangings when I...read more

 

Kentmore Park

Even people who know the Chesapeake Eastern Shore don't know about this little place. After you've crossed the Sassafras River in Georgetown, and you're...read more

 

Hopkins Game Farm

Wow. Just... wow. A business-related trip brought our office here for lunch today. The vegetarians in our party were all "wtf." I'm omnivorous but not...read more

 

Chester 5 Theatres

I watch a ton of movies, and there are worse theatres to be had than Chester 5. The sound isn't phenomenal and there is no stadium seating, but the tickets...read more

 

Kent Athletic & Wellness Ctr

Was visiting family in the area and went to this gym as a IHRSA affiliate (discount from my home gym). The gym was small, and hot. The cardio equipment is...read more

 

National Cryptological Museum

What a fascinating place. I only had an hour to spare but could have spent a lot more time exploring this museum. Our docent was incredibly knowledgeable -...read more

 

Geppi's Entertainment Museum

Comic books are as American as apple pie, Nat King Cole's "Unforgettable", Life Magazine, and baseball. In a matter of minutes Geppi's Entertainment...read more

 

The Senator Theatre

I thought the experience here was time-traveling goodness. I went to see Mr. Smith goes to Washington during their anniversary throw back movies. I am not...read more

 

Empowered Yoga

Damn it's hot in here 106 degrees hot! I visited the first time last week with a very dear friend. I had to make a second trip after my first experience...read more

 

Rams Head On Stage

THE BEST PLACE TO WATCH MUSIC IN MARYLAND!!!!! Talk about getting to hear music as it is supposed to be heard. This is a small venue with tables and as...read more

 

The Metro Gallery

This is a little bitty art gallery/bar/performance space. It was pretty in a modern art way, warm and inviting. There were a few couches and tables...read more

 

Centennial Park

This is a great park! My favorite in the Howard County area by far. They have a huge playground for the children that my son absolutely loves. The little...read more

 

Yelp Baltimore / Yelp DC Joint CMYE @ Paladar in Annapolis!

Woo Hoo! I love CMYE's in Annapolis! Big Props to Kristen and Elsa for putting these things together! So I have been here several times and I can't get...read more

 

B & O Railroad Museum

I haven't actually been to the museum for museum purposes, but I went to it as a venue for a college event. I think it is an amazing venue, with a gorgeous...read more

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Cottage on the Sassafras
Chestertown House Rental Picture
  • bedrooms 2
  • community Kentmore Park
  • rental type House
  • sleeps 5
  • baths 1
  • rates (USD) $900 - $950 /wk
 
 
 
 
 

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Waterfront "GLASS TREE HOUSE" with Boating and Swimming Pier
Chestertown House Rental Picture
  • bedrooms 5
  • community Quaker Neck
  • rental type House
  • sleeps 12
  • baths 2
  • rates (USD) $1,200 - $1,800 /wk
    $995 - $5,800 /mth
 
 
 
 
 

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