25 Best Vacation Rentals in Chestertown - Holiday Lettings - Cabins

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155 Vacation rentals

Cottage rental in Chestertown

Chestertown cottage

4 bedrooms / 3 bathrooms / sleeps 10

13

from $487 / night

$3,664 - $4,466 / week

Vacation home in Chestertown

Chestertown house

3 bedrooms / 2 bathrooms / sleeps 8

19

from $229 / night

$1,489 / week

Chestertown ski apartment to rent.

Chestertown apartment

2 bedrooms / 2 bathrooms / sleeps 6

17

Responds fast! avg. 2 hours 3 minutes

from $172 / night

$745 - $974 / week

Chestertown Vacation log cabin rental

Chestertown log cabin

2 bedrooms / 2 bathrooms / sleeps 4

16

Responds fast! avg. 3 hours 20 minutes

from $172 / night

$1,088 / week

B&b rental in Chestertown

Chestertown b&b

2 bedrooms / 2 bathrooms / sleeps 4

8

from $373 / night

$2,519 - $3,080 / week

Chestertown Vacation cottage rental

Chestertown cottage

2 bedrooms / 2 bathrooms / sleeps 7

3

from $228 / night

$1,373 - $1,574 / week

Vacation home in Chestertown

Chestertown house

3 bedrooms / 3 bathrooms / sleeps 14

3

from $344 / night

$2,290 - $2,405 / week

Vacation home rental

Chestertown house

4 bedrooms / 2 bathrooms / sleeps 10

1

Responds fast! avg. 3 hours 55 minutes

from $147 / night

$1,026 / week

Vacation home in Chestertown

Chestertown house

1 bedroom / 1 bathroom / sleeps 3

Responds fast! avg. 2 hours 47 minutes

from $95 / night

$666 / week

Chestertown Vacation home rental

Chestertown house

4 bedrooms / 4 bathrooms / sleeps 8

Responds fast! avg. 3 hours 55 minutes

from $336 / night

$2,349 / week

Vacation home rental

Chestertown house

2 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 2 hours 47 minutes

from $92 / night

$642 / week

Vacation home in Chestertown

Chestertown house

2 bedrooms / 2 bathrooms / sleeps 7

Responds fast! avg. 3 hours 55 minutes

from $82 / night

$569 / week

Home rental in Chestertown

Chestertown house

4 bedrooms / 2 bathrooms / sleeps 9

Responds fast! avg. 3 hours 55 minutes

from $422 / night

$2,950 / week

Vacation home in Chestertown

Chestertown house

2 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 2 hours 47 minutes

from $117 / night

$818 / week

Vacation chateau in Chestertown

Chestertown chateau

6 bedrooms / 5 bathrooms / sleeps 11

Responds fast! avg. 3 hours 55 minutes

from $845 / night

$5,915 / week

Chestertown Vacation home rental

Chestertown house

2 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 2 hours 47 minutes

from $92 / night

$642 / week

Vacation home in Chestertown

Chestertown house

4 bedrooms / 2 bathrooms / sleeps 11

Responds fast! avg. 3 hours 55 minutes

from $370 / night

$2,589 / week

Chestertown Vacation home rental

Chestertown house

2 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 2 hours 47 minutes

from $95 / night

$666 / week

Chestertown Vacation home rental

Chestertown house

3 bedrooms / 4 bathrooms / sleeps 9

Responds fast! avg. 2 hours 47 minutes

from $127 / night

$890 / week

Vacation home in Chestertown

Chestertown house

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 2 hours 47 minutes

from $100 / night

$698 / week

Vacation home in Chestertown

Chestertown house

6 bedrooms / 4 bathrooms / sleeps 12

Responds fast! avg. 3 hours 55 minutes

from $796 / night

$5,571 / week

Chestertown Vacation home rental

Chestertown house

4 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 3 hours 55 minutes

from $162 / night

$1,131 / week

Vacation home with shared pool in Chestertown

Chestertown house

2 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 2 hours 47 minutes

from $100 / night

$698 / week

Vacation home in Chestertown

Chestertown house

5 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 2 hours 47 minutes

from $235 / night

$1,643 / week

Chestertown Vacation home rental

Chestertown house

1 bedroom / 1 bathroom / sleeps 6

Responds fast! avg. 2 hours 47 minutes

from $70 / night

$489 / week

Vacation home in Chestertown

Chestertown house

5 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 3 hours 55 minutes

from $179 / night

$1,251 / week

Chestertown Vacation home rental

Chestertown house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 3 hours 55 minutes

from $279 / night

$1,948 / week

Great rentals within 20 miles that match your search

Vacation home in Severance

Severance house

5 bedrooms / 2 bathrooms / sleeps 6

1

from $311 / night

$2,176 / week

Vacation home in Severance

Severance house

4 bedrooms / 1 bathroom / sleeps 6

from $295 / night

$2,061 / week

Lake George Vacation cottage rental

Lake George cottage

4 bedrooms / 4 bathrooms / sleeps 10

2

from $241 / night

$1,563 / week

Vacation home rental

Diamond Point house

3 bedrooms / 2 bathrooms / sleeps 8

from $224 / night

$1,369 / week

Vacation cottage in Lake George

Lake George cottage

2 bedrooms / 1 bathroom / sleeps 6

2

from $212 / night

$1,311 / week

Lake George Vacation apartment rental

Lake George apartment

3 bedrooms / 1 bathroom / sleeps 8

2

from $218 / night

$1,443 / week

Vacation home in Diamond Point

Diamond Point house

3 bedrooms / 2 bathrooms / sleeps 8

10

Responds fast! avg. 53 minutes

from $321 / night

$2,245 / week

Cottage rental in Paradox

Paradox cottage

2 bedrooms / 1 bathroom / sleeps 5

Responds fast! avg. 3 hours 15 minutes

from $287 / night

$1,374 / week

Home rental in Warrensburg

Warrensburg house

7 bedrooms / 5 bathrooms / sleeps 17

1

from $2,290 / night

$16,030 / week

Lake George Vacation cottage rental

Lake George cottage

2 bedrooms / 1 bathroom / sleeps 4

from $155 / night

$848 - $1,071 / week

Vacation log cabin in Lake George

Lake George log cabin

3 bedrooms / 2 bathrooms / sleeps 7

1

from $212 / night

$1,277 / week

Vacation cottage with shared pool in Lake George

Lake George cottage

2 bedrooms / 1 bathroom / sleeps 4

from $155 / night

$848 - $1,071 / week

Vacation cottage with shared pool in Lake George

Lake George cottage

1 bedroom / 1 bathroom / sleeps 4

from $126 / night

$733 - $956 / week