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Vacation Rentals in Chestertown, Maryland

about Chestertown

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


Freestate Gun Range

Although I grew up in Maryland, this time I came to visit my family was my first time shooting. And I am hooked. My hands have been itching for a gun more


Schooner Woodwind

My husband took me (plus our 2 month old) for a sunset sail for my birthday last month. It certainly didn't hurt that the weather and wind were more


Heavy Seas Brewing Company

I have actually never been to Heavy Seas for a normal tour, but I have attended the Pyrates, Pigs, and Pints festival two years in a row. The brewery more


Baltimore Museum of Industry

Nice museum that always seems to have children running around in it. It's not too interactive as some have already noted and the exhibits require lots more


Maryland Athletic Club, MAC Harbor East

I was happy with it as the environment is nice and the high price keeps the crowds down. I did register complaints about broken equipment ( more


Sherwood Garden

80,000 tulip bulbs on six acres averages to ... well lots and lots of colorful beauty per square foot, I can assure you. (0.31 bulbs/sq ft, I think - more


Ojas Wellness Center

This establishment is the premier establishment in Mount Washington. The service is top-notch. This is the luxury spa that you are looking for in more


Beltway Movies

A great place to see that movie you missed at the first-run theaters, or to take your kids to see their new favorite movie multiple times, or - if you' more


Sail Selina II

One of the main activities my friends and I wanted to partake in on our trip to St. Michael's was a sailing venture, which we ended up thoroughly more


Maryland Science Center

They have great exhibits but you'll never get to see them. I travelled 1.5 hours to this center/museum to see the Mummy exhibit back in January and I more


National Great Blacks In Wax Museum

3.5 stars. Low lite and emotional as you walk through history. From the first thing we read as we walked in the place. It just puts you back in the more


McFaul's IronHorse Tavern

Had dinner lastnight with a couple of my gals and it was great. The guy who waited on us- Steve was awesome. He was attentive and gave good suggestions more


Ivey League Mixed Martial Arts

I've been training under Master Ives for a couple of years now and he is without a doubt the best coach I have ever trained with. My job has taken me more


The Hippo

I went to The Hippo last night with nine of my closest friends to ring in my birthday and it was FABULOUS. I love that if you're within a week of more


Evolutions Body Clinic

Love this place. It's a small enough gym that it isn't intimidating, but large enough that it has everything you need. The locker rooms are more like more

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* Nightly rates and average rates per bedroom are based on actual rates in this area. Learn More .

Cottage on the Sassafras
Chestertown House Rental Picture
  • bedrooms 2
  • community Kentmore Park
  • rental type House
  • sleeps 5
  • baths 1
  • rates (USD) $950 - $975 /wk

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Waterfront "GLASS TREE HOUSE" with Private Pier
Chestertown House Rental Picture
  • bedrooms 5
  • community Quaker Neck
  • rental type House
  • sleeps 12
  • baths 2
  • rates (USD) $1,100 - $1,800 /wk
    $900 - $6,800 /mth

1 reviews write a review

Waterfront Farm with Pool, Private Dock, Kayaks and WiFi
Chestertown House Rental Picture
  • bedrooms 4
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths 4
  • rates (USD) $400 - $600 /nt
    $2,100 - $3,500 /wk
    $14,100 /mth

13 reviews write a review