Vacation Rentals in Chestertown, Maryland
Search vacation deals on homes, villas, cabins, cottages, apartments and condos in destinations all over the world. Click the "rental results" tab to browse Chestertown, Maryland vacation rentals and inquire about your favorites. If you cant find what youre looking for, consider nearby destinations, or come back for a visit - vacation home rentals in Chestertown are added and updated every week!
Compared to hotels, Chestertown vacation rentals are much more family-friendly and flexible, offering a lot more space, a lot more savings, and a lot more amenities - like private pools, gourmet kitchens, and pet-friendly accommodations! Tip: Save money by taking advantage of cheap weekly rates.
Chestertown, Maryland Vacation Rentals and Tourism
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Chestertown things to do
Chestertown 1st Fridays
I've been studying here in Chestertown since August, and I had heard about 1st Fridays, but this was my first time attending. I had my wife join me on Good...read more
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
Chestertown Marina Inc
Bring your life vest with you when you get off your boat because the dock is sinking! At high tide the water covered the dock in several places and was...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
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
Crow Farm & Vineyard
Only two of four wines available for tastings at this time. Very quaint rustic tasting room. The 2 wines we tasted today were on the dry side, but were...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
Commitment Fitness 24-Hr Gym
The staff is very friendly and helpful and the location is very conveinient! Working out is a big stress reliever for me and there are always trainers...read more
Tucker House
Take in a walk around town with a coffee our lunch. Then stop by and see the historic sites. Well worth an afternoon in this great town.read more
Schooner Woodwind
My husband and I bought tickets on a spur of the moment during the Annapolis Boat Show - what a great idea. Several of us [customers] had a chance to...read more
Heavy Seas Brewing Company
Went on a tour here shortly after moving to Baltimore as something fun to do/cute date idea... my boyfriend was so happy! Don't judge me but since moving...read more
Ojas Wellness Center
getting a prenatal massage as part of my birthday present..and i have to say, I am a fan. I had this amazing prenatal massage done with most focus on my...read more
Baltimore Museum of Industry
I always start with the good! Not this time. There's so much good, let me get the bad out of the way. It's not big enough! There. Goods- This is one HECK...read more
- bedrooms 2
- community Kentmore Park
- rental type House
- sleeps 5
- baths 1
- rates (USD)
$950
- $975
/wk
- bedrooms 5
- community Quaker Neck
- rental type House
- sleeps 12
- baths 2
- rates (USD)
$1,500
- $1,900
/wk
$2,200 - $6,800 /mth
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