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  • Showing 1-50 of 300+
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Additional fees apply. Taxes may be added.
Excellent! 4.6/5
(16 reviews)
avg/night
  • 1 BR
  • 1 BA
  • Sleeps 6
Condo #3896538
16
Viewed 28 times in the last 48 hours
Wonderful! 4.8/5
(15 reviews)
avg/night
  • 2 BR
  • 1 BA
  • Sleeps 6
Condo #716031vb
15
Viewed 49 times in the last 48 hours
Wonderful! 4.8/5
(13 reviews)
avg/night
  • 4 BR
  • 2 BA
  • Sleeps 12
House #4240841
13
Viewed 35 times in the last 48 hours
Very Good! 4.1/5
(7 reviews)
avg/night
  • 2 BR
  • 1 BA
  • Sleeps 5
Condo #3804012
7
Viewed 18 times in the last 48 hours
Excellent! 4.3/5
(18 reviews)
avg/night
  • 2 BR
  • 1 BA
  • Sleeps 6
Cabin #3014265
18
Viewed 72 times in the last 48 hours
Wonderful! 4.9/5
(16 reviews)
avg/night
  • 2 BR
  • 2 BA
  • Sleeps 4
House #4044539
16
Viewed 33 times in the last 48 hours
Very Good! 4/5
(10 reviews)
avg/night
  • 3 BR
  • 3 BA
  • Sleeps 6
Condo #4014526
10
Viewed 47 times in the last 48 hours
Wonderful! 4.9/5
(10 reviews)
avg/night
  • 3 BR
  • 3 BA
  • Sleeps 8
Cottage #175549
10
Viewed 16 times in the last 48 hours
Exceptional! 5/5
(7 reviews)
avg/night
  • 3 BR
  • 3 BA
  • Sleeps 7
Townhome #689905vb
7
Exceptional! 5/5
(6 reviews)
avg/night
  • 3 BR
  • 2 BA
  • Sleeps 10
House #3924952
6
Viewed 15 times in the last 48 hours
Very Good! 4/5
(6 reviews)
avg/night
  • 2 BR
  • 1 BA
  • Sleeps 5
Cabin #3016070
6
Viewed 42 times in the last 48 hours
  • 3 BR
  • 2 BA
  • Sleeps 9
House #4313390
3
Viewed 21 times in the last 48 hours
Wonderful! 4.9/5
(19 reviews)
avg/night
  • 3 BR
  • 2 BA
  • Sleeps 8
House #4073769
19
Viewed 12 times in the last 48 hours
Wonderful! 4.8/5
(21 reviews)
avg/night
  • 3 BR
  • 1 BA
  • Sleeps 8
House #7080936
21
Viewed 29 times in the last 48 hours
Excellent! 4.6/5
(9 reviews)
avg/night
  • 2 BR
  • 1 BA
  • 1 HF BA
  • Sleeps 7
Cottage #3828287
9
Viewed 17 times in the last 48 hours
Exceptional! 5/5
(9 reviews)
avg/night
  • 4 BR
  • 1 BA
  • Sleeps 7
Cottage #3496194
9
Very Good! 4.2/5
(14 reviews)
avg/night
  • 6 BR
  • 3 BA
  • Sleeps 26
House #258920
14
Viewed 28 times in the last 48 hours
avg/night
  • 4 BR
  • 2 BA
  • Sleeps 8
Cottage #1020543vb
2
Viewed 26 times in the last 48 hours
  • 6 BR
  • 3 BA
  • Sleeps 12
House #557834vb
1
Viewed 13 times in the last 48 hours
avg/night
  • 7 BR
  • 4 BA
  • Sleeps 18
House #1034527vb
Viewed 38 times in the last 48 hours
Excellent! 4.6/5
(16 reviews)
avg/night
  • 2 BR
  • 2 BA
  • 1 HF BA
  • Sleeps 8
Cabin #641786vb
16
Viewed 17 times in the last 48 hours
avg/night
  • 2 BR
  • 2 BA
  • Sleeps 6
Cabin #4087680
Viewed 50 times in the last 48 hours
  • 2 BR
  • 1 BA
  • 1 HF BA
  • Sleeps 7
Condo #1036429vb
Viewed 42 times in the last 48 hours
avg/night
  • 4 BR
  • 2 BA
  • 1 HF BA
  • Sleeps 8
Chalet #593993vb
Viewed 9 times in the last 48 hours
  • 6 BR
  • 2 BA
  • Sleeps 11
Lodge #3727616
1
Viewed 25 times in the last 48 hours
avg/night
  • 4 BR
  • 2 BA
  • Sleeps 13
House #948569vb
Viewed 11 times in the last 48 hours
avg/night
  • 2 BR
  • 1 BA
  • Sleeps 8
Cottage #4473478
1
Viewed 13 times in the last 48 hours
Exceptional! 5/5
(31 reviews)
avg/night
  • 3 BR
  • 2 BA
  • Sleeps 9
Chalet #3348vb
31
Viewed 11 times in the last 48 hours
avg/night
  • 3 BR
  • 2 BA
  • Sleeps 9
House #4479049
Viewed 16 times in the last 48 hours
  • 2 BR
  • 1 BA
  • Sleeps 6
Apartment #948565vb
3
Viewed 9 times in the last 48 hours
avg/night
  • 1 BR
  • 1 BA
  • Sleeps 2
Cabin #1021229vb
Viewed 8 times in the last 48 hours
avg/night
  • 1 BR
  • 1 BA
  • Sleeps 4
Cabin #4537664
1
Viewed 20 times in the last 48 hours
  • 5 BR
  • 2 BA
  • Sleeps 8
House #239560
Viewed 7 times in the last 48 hours
avg/night
  • 4 BR
  • 1 BA
  • Sleeps 7
Cottage #3667204
1
Viewed 7 times in the last 48 hours
avg/night
  • 4 BR
  • 4 BA
  • 1 HF BA
  • Sleeps 16
Apartment #3726412
1
Viewed 21 times in the last 48 hours
Wonderful! 4.9/5
(76 reviews)
avg/night
  • 5 BR
  • 3 BA
  • 1 HF BA
  • Sleeps 18
House #179508
76
Viewed 145 times in the last 48 hours
Exceptional! 5/5
(105 reviews)
avg/night
  • 7 BR
  • 6 BA
  • 1 HF BA
  • Sleeps 19
House #3001286
105
Viewed 121 times in the last 48 hours
Wonderful! 4.8/5
(12 reviews)
avg/night
  • 3 BR
  • 2 BA
  • Sleeps 7
House #863326vb
12
Viewed 126 times in the last 48 hours
Wonderful! 4.9/5
(12 reviews)
avg/night
  • 2 BR
  • 1 BA
  • Sleeps 6
Cabin #802195vb
12
Viewed 183 times in the last 48 hours
Wonderful! 4.9/5
(38 reviews)
avg/night
  • 6 BR
  • 3 BA
  • 2 HF BA
  • Sleeps 15
House #3876403
38
Viewed 47 times in the last 48 hours
Excellent! 4.4/5
(14 reviews)
avg/night
  • 2 BR
  • 1 BA
  • Sleeps 4
Cabin #7006524
14
Viewed 54 times in the last 48 hours
Exceptional! 5/5
(26 reviews)
avg/night
  • 2 BR
  • 1 BA
  • Sleeps 6
Cottage #3678055
26
Viewed 10 times in the last 48 hours
Wonderful! 4.9/5
(17 reviews)
avg/night
  • 1 BR
  • 1 BA
  • Sleeps 2
Cabin #4066619
17
Viewed 17 times in the last 48 hours
Wonderful! 4.9/5
(49 reviews)
avg/night
  • 3 BR
  • 2 BA
  • Sleeps 10
House #423420vb
49
Viewed 81 times in the last 48 hours
Exceptional! 5/5
(42 reviews)
avg/night
  • 6 BR
  • 4 BA
  • Sleeps 19
House #3858756
42
Viewed 28 times in the last 48 hours
Excellent! 4.3/5
(10 reviews)
avg/night
  • 2 BR
  • 1 BA
  • Sleeps 5
Cottage #3953323
10
Viewed 18 times in the last 48 hours
Wonderful! 4.8/5
(11 reviews)
avg/night
  • 4 BR
  • 3 BA
  • 1 HF BA
  • Sleeps 11
Townhome #145704
11
Viewed 103 times in the last 48 hours
Exceptional! 5/5
(16 reviews)
avg/night
  • 3 BR
  • 2 BA
  • Sleeps 8
Cabin #976461
16
Viewed 115 times in the last 48 hours
Wonderful! 4.8/5
(20 reviews)
avg/night
  • 5 BR
  • 3 BA
  • Sleeps 12
House #189443
20
Viewed 86 times in the last 48 hours
Very Good! 4.1/5
(14 reviews)
avg/night
  • 3 BR
  • 2 BA
  • Sleeps 10
House #3969518
14
Viewed 127 times in the last 48 hours
  • 1 - 50 of 300+

Vacation Rentals in Chestertown, New York (300+)