5 Best Vacation Rentals in Chestertown - Holiday Lettings - Cabins

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Chestertown

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7 Vacation rentals

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(2) Very Good 

11

Maryland / Chestertown

3 7 2 nights min

  • 3 bedrooms
  • Sleeps 7
  • 2 nights min
  • Child friendly

 …see more

from $145 / night

$941 - $1150 / week

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from $145 / night

(3) Excellent 

28

Maryland / Chestertown

1 4 7 nights min

  • 1 bedroom
  • Sleeps 4
  • 7 nights min
  • Nearest beach 2 mi
  • Child friendly
  • Air conditioning

 …see more

from $120 / night

$650 / week

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from $120 / night

(6) Excellent 

10

Maryland / Chestertown

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Nearest beach 24 mi
  • Child friendly
  • Air conditioning

 …see more

from $99 / night

$686 / week

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from $99 / night

(1) Excellent 

21

Maryland / Chestertown

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning

 …see more

from $156 / night

$901 - $1101 / week

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from $156 / night

(1) Excellent 

16

Maryland / Chestertown

4 8 2 nights min

  • 4 bedrooms
  • Sleeps 8
  • 2 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning

 …see more

from $451 / night

$3151 / week

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from $451 / night

(3) Very Good 

22

Maryland / Chestertown

3 8 2 nights min

  • 3 bedrooms
  • Sleeps 8
  • 2 nights min
  • Child friendly
  • Air conditioning

 …see more

from $296 / night

$1995 / week

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from $296 / night

14

Maryland / Chestertown

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Child friendly
  • Air conditioning
  • Private garden

 …see more

from $111 / night

$650 - $1070 / week

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from $111 / night