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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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Weekly rate:

Min $0, Max $4000

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$2,000
$4,000+

Bedrooms: Min 0, Max 5

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5+







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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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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

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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