COVID-19 Update: The impact of COVID-19 on travel is unprecedented. Like you, we’re monitoring the situation. Rest assured, we’re here to help with questions about your plans. Learn more here: About the coronavirus outbreak (COVID-19)

Updating

5 Best Vacation Rentals in Chestertown - Holiday Lettings - Cabins

All filters

Filters

63 Vacation rentals

Cottage rental in Chestertown

Chestertown cottage

4 bedrooms • 3 bathrooms • sleeps 10

15 reviews

from $573 / night

$4,122 - $4,924 / week

1 / 36

Chestertown Vacation cottage rental

Chestertown cottage

2 bedrooms • 2 bathrooms • sleeps 7

3 reviews

from $308 / night

$2,862 - $3,263 / week

1 / 22

Vacation home in Chestertown

Chestertown house

3 bedrooms • 2 bathrooms • sleeps 8

20 reviews

from $247 / night

$1,724 / week

1 / 36

B&b rental in Chestertown

Chestertown b&b

2 bedrooms • 2 bathrooms • sleeps 4

9 reviews

from $401 / night

$2,977 - $3,779 / week

1 / 24

Chestertown ski apartment to rent.

Chestertown apartment

2 bedrooms • 2 bathrooms • sleeps 6

19 reviews

from $172 / night

$974 / week

1 / 25

Vacation home in Chestertown

Chestertown house

4 bedrooms • 2 bathrooms • sleeps 11

from $487 / night

$3,407 / week

1 / 37

Home rental in Chestertown

Chestertown house

4 bedrooms • 2 bathrooms • sleeps 9

from $410 / night

$2,870 / week

1 / 40

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

1 / 5

Bolton Landing Vacation cottage rental

Bolton Landing cottage

2 bedrooms • 1 bathroom • sleeps 6

from $270 / night

$1,890 / week

1 / 18

Vacation home in Cleverdale

Cleverdale house

3 bedrooms • 2 bathrooms • sleeps 8

from $527 / night

$3,687 / week

1 / 16

Vacation cottage in Cleverdale

Cleverdale cottage

1 bedroom • 1 bathroom • sleeps 3

from $229 / night

$1,603 / week

1 / 13

Paradox Vacation home rental

Paradox house

4 bedrooms • 3 bathrooms • sleeps 8

from $524 / night

$3,664 / week

1 / 25

Vacation home in Pottersville

Pottersville house

3 bedrooms • 1 bathroom • sleeps 6

from $217 / night

$1,515 / week

1 / 29

Bolton Landing Vacation townhouse rental

Bolton Landing townhouse

4 bedrooms • 4 bathrooms • sleeps 10

from $282 / night

$1,972 / week

1 / 29

Fort Ann Vacation tented camp rental

Fort Ann tented camp

8 bedrooms • 8 bathrooms • sleeps 4

from $58 / night

$401 / week

1 / 13

Bolton Landing Vacation cottage rental

Bolton Landing cottage

2 bedrooms • 1 bathroom • sleeps 8

from $436 / night

$3,046 / week

1 / 71

Vacation home in Severance

Severance house

3 bedrooms • 2 bathrooms • sleeps 6

from $338 / night

$2,205 - $2,680 / week

1 / 11

Vacation cottage in Pottersville

Pottersville cottage

4 bedrooms • 1 bathroom • sleeps 4

16 reviews

from $172 / night

$945 / week

1 / 15

Ski log cabin to rent in Johnsburg

Johnsburg log cabin

3 bedrooms • 3 bathrooms • sleeps 16

from $745 / night

$5,153 / week

1 / 17

Lake George Vacation home rental

Lake George house

4 bedrooms • 4 bathrooms • sleeps 11

3 reviews

from $458 / night

$3,206 / week

1 / 20

Vacation home in Severance

Severance house

3 bedrooms • 1 bathroom • sleeps 8

2 reviews

from $321 / night

$2,004 - $2,497 / week

1 / 11

Vacation home in Schroon Lake

Schroon Lake house

3 bedrooms • 5 bathrooms • sleeps 12

from $516 / night

$3,435 / week

1 / 11

Vacation home in Severance

Severance house

5 bedrooms • 2 bathrooms • sleeps 6

1 review

from $321 / night

$2,176 - $2,680 / week

1 / 12

Severance Vacation home rental

Severance house

3 bedrooms • 1 bathroom • sleeps 6

from $287 / night

$1,976 - $2,308 / week

1 / 11

Vacation home in Severance

Severance house

4 bedrooms • 1 bathroom • sleeps 6

from $298 / night

$2,061 - $2,451 / week

1 / 5

Vacation home in Severance

Severance house

4 bedrooms • 2 bathrooms • sleeps 8

5 reviews

from $321 / night

$2,176 - $2,840 / week

1 / 12

Vacation home in Severance

Severance house

4 bedrooms • 1 bathroom • sleeps 6

3 reviews

from $298 / night

$2,119 - $2,422 / week

1 / 9

Vacation home in Severance

Severance house

5 bedrooms • 2 bathrooms • sleeps 6

from $321 / night

$2,176 - $2,680 / week

1 / 8

Vacation log cabin rental

Warrensburg log cabin

4 bedrooms • 3 bathrooms • sleeps 8

1 review

from $453 / night

$2,863 / week

1 / 20

Vacation log cabin in North Creek

North Creek log cabin

2 bedrooms • 1 bathroom • sleeps 4

13 reviews

from $201 / night

$1,203 - $1,603 / week

1 / 20

Schroon Lake ski home to rent.

Schroon Lake house

5 bedrooms • 4 bathrooms • sleeps 14

from $567 / night

$3,968 / week

1 / 28

Vacation cottage with shared pool in Lake George

Lake George cottage

2 bedrooms • 1 bathroom • sleeps 6

from $331 / night

$1,586 / week

1 / 10

Lake George Vacation chalet rental

Lake George chalet

3 bedrooms • 2 bathrooms • sleeps 8

1 review

from $200 / night

$954 - $1,435 / week

1 / 14

Vacation home in Diamond Point

Diamond Point house

4 bedrooms • 2 bathrooms • sleeps 10

from $572 / night

$3,664 / week

1 / 7

Vacation home in Severance

Severance house

5 bedrooms • 2 bathrooms • sleeps 8

3 reviews

from $298 / night

$2,061 - $2,554 / week

1 / 10

Vacation home in Diamond Point

Diamond Point house

3 bedrooms • 2 bathrooms • sleeps 8

13 reviews

from $321 / night

$2,245 / week

1 / 19

Bakers Mills Vacation lodge rental

Bakers Mills lodge

3 bedrooms • 1 bathroom • sleeps 8

1 review

from $172 / night

$1,145 - $1,546 / week

1 / 11

Severance Vacation home accommodation

Severance house

1 bedroom • 1 bathroom • sleeps 2

from $157 / night

$1,088 - $1,260 / week

1 / 5

Lake George Vacation home rental

Lake George house

4 bedrooms • 5 bathrooms • sleeps 10

from $591 / night

$4,136 / week

1 / 44

Cottage rental in Athol

Athol cottage

2 bedrooms • 2 bathrooms • sleeps 6

from $261 / night

$1,828 / week

1 / 25