10 Best Vacation Rentals in Chestertown - Holiday Lettings - Cabins

Close

Chestertown

No dates Enter dates for accurate prices -

Adults, Children

Enter dates for more accurate prices

Payment Protection
To book this vacation rental you need to pay through the Holiday Lettings website. We can’t protect your payment if you don’t pay through us. Learn more

12 Vacation rentals

(12) Excellent 

34

New York / Chestertown

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Child friendly

 …see more

from $196 / night

$1225 - $1400 / week

Book View

from $196 / night

(11) Excellent 

25

New York / Chestertown

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Ski

 …see more

from $151 / night

$600 - $1250 / week

Book View

from $151 / night

(4) Excellent 

6

New York / Chestertown

4 16 2 nights min

  • 4 bedrooms
  • Sleeps 16
  • 2 nights min
  • Nearest beach 2 mi
  • Child friendly
  • Air conditioning

 …see more

from $498 / night

$1496 - $4295 / week

Book View

from $498 / night

(10) Excellent 

34

New York / Chestertown

4 10 7 nights min

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 26 mi
  • Child friendly

 …see more

from $400 / night

$3000 - $3701 / week

Book View

from $400 / night

(6) Excellent 

23

New York / Chestertown

2 4 2 nights min

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

 …see more

from $251 / night

$1800 - $2700 / week

Book View

from $251 / night

(5) Excellent 

19

New York / Chestertown

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Ski

 …see more

from $151 / night

$1050 - $1300 / week

Book View

from $151 / night

(8) Excellent 

18

New York / Chestertown

3 6 2 nights min

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min
  • Nearest beach 5 mi
  • Child friendly
  • Private garden

 …see more

from $151 / night

$950 / week

Book View

from $151 / night

42

New York / Chestertown

4 10 2 nights min

  • 4 bedrooms
  • Sleeps 10
  • 2 nights min
  • Child friendly

 …see more

from $451 / night

$2900 / week

Book View

from $451 / night

9

New York / Chestertown

2 5 2 nights min

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min
  • Air conditioning
  • Pet friendly

 …see more

from $160 / night

$901 / week

Book View

from $160 / night

22

New York / Chestertown

19 12 7 nights min

  • 19 bedrooms
  • Sleeps 12
  • 7 nights min
  • Child friendly
  • Pet friendly

 …see more

from $100 / night

$701 / week

Book View

from $100 / night

10

New York / Chestertown

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning

 …see more

from $176 / night

$996 / week

Book View

from $176 / night

22

New York / Chestertown

2 7 2 nights min

  • 2 bedrooms
  • Sleeps 7
  • 2 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Pet friendly

 …see more

from $159 / night

$1500 / week

Book View

from $159 / night