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Vacation Rentals in Chestertown, Maryland

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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


Schooner Woodwind

So glad we did this! My fiance and I decided to do the two hour trip and it was perfect. The captain and crew were attentive, funny, but not more


Freestate Gun Range

No fuss no attitude .The range master asked some basic questions and gave a safety briefing and off to the range I went. They were helpful . I took my 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

Just joined today and looking forward to starting swimming lessons. This review is focused on the signing up process. Sherryl warmly greeted us. She 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


Sherwood Garden

stop and smell the flowers. why? they just smell like... flowers... i'm not much of a flower person, but visiting this 6 acre open space filled with more


Ojas Wellness Center

I am a huge fan of this place. The staff is so great and they are open late, so you can get your spa time in after work. I go with Ashby for my more


Beltway Movies

Honestly I love this place. The prices are great and the theaters are nice. They have a decent selection of films and the staff that I have dealt with more


Sail Selina II

When it comes to rating stars, I wish there were more than 5!!! Selina II, Captain Iris and her first mate (Frank) provided an unforgettable more


McFaul's IronHorse Tavern

I've driven by this place a few times and never thought anything of it until I pulled it up on Yelp and saw the number of high ratings. At that point, more


National Great Blacks In Wax Museum

WOW what a hidden gem! The exhibit starts with a basement replica of the bowels of a slave ship. The life-like wax figures and descriptions of the more


Maryland Science Center

I remember coming here as a child on a field trip-and that's clearly their bread and butter. My boyfriend and I-both in our mid-late 20's-decided to more


The Hippo

Karaoke!!!! I love, love, love The Hippo for impromptu and totally random fun. No matter the night they have awesomely priced drinks and colorful 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


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 .

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) $1,200 - $1,800 /wk
    $900 - $5,000 /mth

1 reviews write a review

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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Chesapeake Bay Waterfront Home, Huge Deck, Spectacular Sunsets, 2 Fireplaces
Chestertown House Rental Picture
  • bedrooms 5
  • rental type House
  • sleeps 12
  • baths 3
  • rates (USD) $375 - $500 /nt
    $2,500 - $3,500 /wk

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Beautiful Cottage On Maryland's Eastern Shore
Chestertown Cottage Rental Picture
  • bedrooms 3
  • rental type Cottage
  • sleeps 8
  • baths
  • rates (USD) $186 - $300 /nt
    $1,300 /wk

2 reviews write a review

Stunning Home on a 25-acre Private Woodland Estate
Chestertown Estate Rental Picture
  • bedrooms 4
  • rental type Estate
  • sleeps 10
  • baths
  • rates (USD) $500 - $600 /nt
    $3,500 /wk
    $10,000 /mth

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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

14 reviews write a review