Help on Feeds

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

more destinations

Check out more areas which feature homes, villas, cabins, cottages, or condos.

rental results

availability


Weekly rate:

Min $0, Max $4000

$0
$2,000
$4,000+

Bedrooms: Min 0, Max 5

0
5+







Property Type:


legend

savings
freebies
has photos
has calendar
has swimming pool
has hot tub
pets allowed
owner badge

* 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
 
 
 
 
 

write a review

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