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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


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


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


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

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


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

This place was really nice! Lots of parking, discounted price for the 3D movie ($5.50), clean and very friendly people. I will definitely be coming more


Sail Selina II

We decided to do our wedding ceremony aboard the Salina II on our anniversary. Capt. Iris and crew were amazing! Despite the bleak weather and more


National Great Blacks In Wax Museum

I'd give this place a 4.5. The NGBIWM is situated in East unexpected gem about 2 miles off the tourist route of downtown and the more


McFaul's IronHorse Tavern

Stopped by on a Thursday evening during the summer for dinner. Parking was hard to come by, and while there were a few seats inside, there were no 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


Jonas Green Park

Beautiful place to sit and chill while enjoying the awesome weather, view, and peacefulness. We brought crab and lobster rolls and ice cream and it was more


Ivey League Mixed Martial Arts

Beware. I went here for my aspergers son and they assured they could deal with him. After about 10 classes I was so disapponted by the instructor, 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

write a review

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

2 reviews write a review

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

3 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

15 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) $350 - $700 /nt
    $3,000 - $3,500 /wk
    $6,500 - $10,000 /mth

2 reviews write a review