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25 Best Vacation Rentals in Chestertown - Holiday Lettings - Cabins

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103 Vacation rentals

Cottage rental in Chestertown

Chestertown cottage

4 bedrooms / 3 bathrooms / sleeps 10

15

from $544 / night

$3,893 - $4,695 / week

Chestertown Vacation cottage rental

Chestertown cottage

2 bedrooms / 2 bathrooms / sleeps 7

3

Responds fast! avg. 2 hours 45 minutes

from $228 / night

$1,488 - $1,688 / week

Vacation home in Chestertown

Chestertown house

3 bedrooms / 2 bathrooms / sleeps 8

20

from $247 / night

$1,718 / week

B&b rental in Chestertown

Chestertown b&b

2 bedrooms / 2 bathrooms / sleeps 4

9

from $401 / night

$2,748 - $3,550 / week

Chestertown ski apartment to rent.

Chestertown apartment

2 bedrooms / 2 bathrooms / sleeps 6

18

Responds fast! avg. 3 hours 12 minutes

from $172 / night

$974 - $1,432 / week

Vacation home in Chestertown

Chestertown house

6 bedrooms / 4 bathrooms / sleeps 12

from $777 / night

$5,435 / week

Vacation home in Chestertown

Chestertown house

4 bedrooms / 2 bathrooms / sleeps 11

Responds fast! avg. 3 hours 37 minutes

from $487 / night

$3,407 / week

Vacation home in Chestertown

Chestertown house

2 bedrooms / 2 bathrooms / sleeps 5

from $235 / night

$1,643 / week

Chestertown Vacation home rental

Chestertown house

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 1 hour 36 minutes

from $211 / night

$1,475 / week

Vacation home in Chestertown

Chestertown house

5 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 2 hours 11 minutes

from $242 / night

$1,692 / week

Vacation home rental

Chestertown house

4 bedrooms / 2 bathrooms / sleeps 6

1

from $166 / night

$1,163 / week

Vacation chateau in Chestertown

Chestertown chateau

6 bedrooms / 5 bathrooms / sleeps 11

from $843 / night

$5,899 / week

Vacation home in Chestertown

Chestertown house

2 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 1 hour 36 minutes

from $243 / night

$1,700 / week

Vacation home rental

Chestertown house

2 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 2 hours 11 minutes

from $260 / night

$1,820 / week

Chestertown Vacation home rental

Chestertown house

3 bedrooms / 2 bathrooms / sleeps 6

from $322 / night

$2,253 / week

Vacation home with shared pool in Chestertown

Chestertown house

2 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 2 hours 11 minutes

from $240 / night

$1,676 / week

Home rental in Chestertown

Chestertown house

4 bedrooms / 2 bathrooms / sleeps 9

Responds fast! avg. 3 hours 37 minutes

from $410 / night

$2,870 / week

Vacation home with shared pool in Chestertown

Chestertown house

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 2 hours 19 minutes

from $164 / night

$1,147 / week

Vacation home in Chestertown

Chestertown house

1 bedroom / 1 bathroom / sleeps 3

Responds fast! avg. 2 hours 19 minutes

from $154 / night

$1,074 / week

Chestertown Vacation home rental

Chestertown house

4 bedrooms / 2 bathrooms / sleeps 8

from $225 / night

$1,571 / week

Vacation home in Chestertown

Chestertown house

5 bedrooms / 3 bathrooms / sleeps 6

from $535 / night

$3,743 / week

Chestertown Vacation home rental

Chestertown house

4 bedrooms / 4 bathrooms / sleeps 8

from $328 / night

$2,293 / week

Chestertown Vacation home rental

Chestertown house

1 bedroom / 1 bathroom / sleeps 6

Responds fast! avg. 1 hour 36 minutes

from $280 / night

$1,956 / week

Chestertown Vacation home rental

Chestertown house

4 bedrooms / 4 bathrooms / sleeps 8

from $362 / night

$2,533 / week

Home rental in Chestertown

Chestertown house

3 bedrooms / 2 bathrooms / sleeps 6

from $216 / night

$1,507 / week

Great rentals within 20 miles that match your search

Olmstedville ski log cabin to rent.

Olmstedville log cabin

2 bedrooms / 3 bathrooms / sleeps 10

from $544 / night

$2,863 / week

Bolton Landing Vacation cottage rental

Bolton Landing cottage

2 bedrooms / 1 bathroom / sleeps 6

from $270 / night

$1,890 / week

Vacation home in Cleverdale

Cleverdale house

3 bedrooms / 2 bathrooms / sleeps 8

from $527 / night

$3,687 / week

Vacation cottage in Cleverdale

Cleverdale cottage

1 bedroom / 1 bathroom / sleeps 3

from $229 / night

$1,603 / week

Lake George Vacation chalet rental

Lake George chalet

3 bedrooms / 2 bathrooms / sleeps 8

1

from $137 / night

$954 - $1,435 / week

Bolton Landing Vacation cottage rental

Bolton Landing cottage

2 bedrooms / 1 bathroom / sleeps 8

from $436 / night

$3,046 / week

Lake George Vacation home rental

Lake George house

4 bedrooms / 4 bathrooms / sleeps 11

3

Responds fast! avg. 3 hours 23 minutes

from $458 / night

$3,206 / week

Vacation cottage with shared pool in Lake George

Lake George cottage

2 bedrooms / 1 bathroom / sleeps 6

from $304 / night

$1,466 / week

Paradox Vacation home rental

Paradox house

4 bedrooms / 3 bathrooms / sleeps 8

from $524 / night

$3,664 / week

Vacation home in Pottersville

Pottersville house

3 bedrooms / 1 bathroom / sleeps 6

from $217 / night

$1,515 / week

Vacation cottage in Pottersville

Pottersville cottage

4 bedrooms / 1 bathroom / sleeps 4

16

from $155 / night

$945 / week

Bolton Landing Vacation townhouse rental

Bolton Landing townhouse

4 bedrooms / 4 bathrooms / sleeps 10

Responds fast! avg. 3 hours 37 minutes

from $282 / night

$1,972 / week

Vacation home in Severance

Severance house

4 bedrooms / 1 bathroom / sleeps 6

3

from $298 / night

$2,119 - $2,422 / week

Vacation home in Severance

Severance house

5 bedrooms / 2 bathrooms / sleeps 8

3

from $298 / night

$2,061 - $2,554 / week

Vacation home in Severance

Severance house

5 bedrooms / 2 bathrooms / sleeps 6

from $321 / night

$2,176 - $2,680 / week