Vacation Rentals in Chestertown, Maryland
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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
- bedrooms 2
- community Kentmore Park
- rental type House
- sleeps 5
- baths 1
- rates (USD)
$900
- $950
/wk
- bedrooms 5
- community Quaker Neck
- rental type House
- sleeps 12
- baths 2
- rates (USD)
$1,200
- $1,800
/wk
$995 - $5,800 /mth







