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25 Best Vacation Rentals in Chestertown - Holiday Lettings - Cabins

151 Vacation rentals

Vacation home in Chestertown

Chestertown house

19

  • Beach/lakeside relaxation
  • •  Child friendly
  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from $229 / night

$1,489 / week

Cottage rental in Chestertown

Chestertown cottage

13

  • Beach/lakeside relaxation
  • •  Nearest beach 26 mi
  • •  Child friendly
  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

from $487 / night

$3,664 - $4,466 / week

Chestertown Vacation cottage rental

Chestertown cottage

3

  • Beach/lakeside relaxation
  • •  Nearest beach 0.1 mi
  • •  Child friendly
  • 2 bedrooms
  • 2 bathrooms
  • sleeps 7

from $228 / night

$1,373 - $1,574 / week

Chestertown Vacation log cabin rental

Chestertown log cabin

16

  • Nearest beach 5 mi
  • •  Child friendly
  • •  Private garden
  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $172 / night

$1,088 / week

B&b rental in Chestertown

Chestertown b&b

8

  • Beach/lakeside relaxation
  • •  Child friendly
  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $373 / night

$2,519 - $3,080 / week

Chestertown ski apartment to rent.

Chestertown apartment

17

  • Beach/lakeside relaxation
  • •  Nearest beach 0 mi
  • •  Ski
  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $172 / night

$916 / week

Vacation chateau in Chestertown

Chestertown chateau

  • Child friendly
  • •  Car not necessary
  • •  Air conditioning
  • 6 bedrooms
  • 5 bathrooms
  • sleeps 11

from $233 / night

$1,627 / week

Vacation home in Chestertown

Chestertown house

  • Child friendly
  • •  Car not necessary
  • •  Pet friendly
  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from $235 / night

$1,643 / week

Vacation home with shared pool in Chestertown

Chestertown house

  • Swimming pool
  • •  Child friendly
  • •  Car not necessary
  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

from $166 / night

$1,163 / week

Vacation home in Chestertown

Chestertown house

  • Child friendly
  • •  Car not necessary
  • 2 bedrooms
  • 2 bathrooms
  • sleeps 7

from $82 / night

$569 / week

Vacation home in Chestertown

Chestertown house

  • Child friendly
  • •  Car not necessary
  • 6 bedrooms
  • 4 bathrooms
  • sleeps 12

from $772 / night

$5,403 / week

Home rental in Chestertown

Chestertown house

  • Child friendly
  • •  Car not necessary
  • 4 bedrooms
  • 2 bathrooms
  • sleeps 9

from $477 / night

$3,335 / week

Vacation home in Chestertown

Chestertown house

  • Child friendly
  • •  Car not necessary
  • 4 bedrooms
  • 2 bathrooms
  • sleeps 11

from $503 / night

$3,519 / week

Chestertown Vacation home rental

Chestertown house

  • Swimming pool
  • •  Child friendly
  • •  Car not necessary
  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from $100 / night

$698 / week

Vacation home in Chestertown

Chestertown house

  • Swimming pool
  • •  Child friendly
  • •  Car not necessary
  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

from $168 / night

$1,171 / week

Chestertown Vacation home rental

Chestertown house

  • Child friendly
  • •  Car not necessary
  • •  Pet friendly
  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from $275 / night

$1,924 / week

Chestertown Vacation home rental

Chestertown house

  • Swimming pool
  • •  Child friendly
  • •  Car not necessary
  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from $116 / night

$810 / week

Vacation home in Chestertown

Chestertown house

  • Swimming pool
  • •  Child friendly
  • •  Car not necessary
  • 5 bedrooms
  • 3 bathrooms
  • sleeps 4

from $122 / night

$850 / week

Vacation home rental

Chestertown house

  • Swimming pool
  • •  Child friendly
  • •  Car not necessary
  • 5 bedrooms
  • 2 bathrooms
  • sleeps 8

from $99 / night

$690 / week

Chestertown Vacation home rental

Chestertown house

  • Child friendly
  • •  Car not necessary
  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

from $190 / night

$1,331 / week

Vacation home rental

Chestertown house

1

  • Child friendly
  • •  Car not necessary
  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

from $146 / night

$1,018 / week

Vacation home in Chestertown

Chestertown house

  • Child friendly
  • •  Car not necessary
  • 5 bedrooms
  • 3 bathrooms
  • sleeps 6

from $290 / night

$2,028 / week

Vacation home in Chestertown

Chestertown house

3

  • Child friendly
  • •  Private garden
  • 3 bedrooms
  • 3 bathrooms
  • sleeps 14

from $344 / night

$2,290 - $2,405 / week

Chestertown Vacation home rental

Chestertown house

  • Child friendly
  • •  Car not necessary
  • •  Air conditioning
  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from $276 / night

$1,932 / week

Chestertown Vacation home rental

Chestertown house

  • Child friendly
  • 4 bedrooms
  • 2 bathrooms
  • sleeps 6

from $100 / night

$698 / week

Great rentals within 20 miles that match your search

Vacation cottage with shared pool in Lake George

Lake George cottage

  • Swimming pool
  • •  Child friendly
  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

from $304 / night

$1,466 / week

Vacation log cabin rental

Warrensburg log cabin

1

  • Beach/lakeside relaxation
  • •  Nearest beach 0.5 mi
  • •  Child friendly
  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from $338 / night

$2,233 / week

Cottage rental in Paradox

Paradox cottage

  • Child friendly
  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

from $229 / night

$1,203 / week

Vacation home in Severance

Severance house

  • Beach/lakeside relaxation
  • •  Nearest beach 0 mi
  • •  Child friendly
  • 4 bedrooms
  • 1 bathroom
  • sleeps 6

from $295 / night

$2,061 / week

Vacation cottage with shared pool in Lake George

Lake George cottage

  • Swimming pool
  • •  Child friendly
  • •  Air conditioning
  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from $126 / night

$733 - $813 / week

Lake George Vacation home rental

Lake George house

  • Swimming pool
  • •  Child friendly
  • •  Air conditioning
  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from $138 / night

$762 - $842 / week

Cottage rental in Paradox

Paradox cottage

  • Child friendly
  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

from $229 / night

$1,203 / week

Vacation cottage with shared pool in Lake George

Lake George cottage

1

  • Swimming pool
  • •  Child friendly
  • •  Air conditioning
  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

from $149 / night

$808 - $1,128 / week

Vacation home in Johnsburg

Johnsburg house

22

  • Ask about children
  • •  Air conditioning
  • •  Ask about pets
  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

from $201 / night

$1,203 - $1,804 / week

Lake George Vacation cottage rental

Lake George cottage

  • Swimming pool
  • •  Child friendly
  • •  Air conditioning
  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

from $149 / night

$808 - $1,128 / week

Lake George Vacation cottage rental

Lake George cottage

2

  • Beach/lakeside relaxation
  • •  Child friendly
  • •  Air conditioning
  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

from $241 / night

$1,563 / week

Vacation home in Severance

Severance house

2

  • Child friendly
  • •  Pet friendly
  • •  Private garden
  • 4 bedrooms
  • 1 bathroom
  • sleeps 6

from $291 / night

$2,033 - $2,193 / week

Vacation cottage in Lake George

Lake George cottage

5

  • Beach/lakeside relaxation
  • •  Child friendly
  • •  Air conditioning
  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from $229 / night

$1,443 / week

Home rental in Lake George

Lake George house

2

  • Beach/lakeside relaxation
  • •  Child friendly
  • •  Air conditioning
  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from $195 / night

$1,140 / week

Minerva Vacation bungalow rental

Minerva bungalow

2

  • Child friendly
  • •  Private garden
  • 3 bedrooms
  • 1 bathroom
  • sleeps 8

from $172 / night

$1,203 / week