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Exceptional! 5/5
(11 reviews)
avg/night
  • 3 BR
  • 2 BA
  • Sleeps 6
House #220506vb
11
Exceptional! 5/5
(7 reviews)
avg/night
  • 3 BR
  • 2 BA
  • Sleeps 6
House #759063vb
7
  • 4 BR
  • 3 BA
  • Sleeps 8
House #4487352
Viewed 7 times in the last 48 hours
avg/night
  • 3 BR
  • 3 BA
  • Sleeps 8
House #1054955vb
Viewed 8 times in the last 48 hours
avg/night
  • 1 BR
  • 1 BA
  • Sleeps 2
Apartment #975033vb
Viewed 5 times in the last 48 hours
  • 4 BR
  • 2 BA
  • 1 HF BA
  • Sleeps 8
House #4558937
Exceptional! 5/5
(50 reviews)
avg/night
  • 3 BR
  • 3 BA
  • Sleeps 8
House #294688vb
50
Exceptional! 5/5
(22 reviews)
avg/night
  • 2 BR
  • 2 BA
  • Sleeps 5
Cottage #608459vb
22
Viewed 6 times in the last 48 hours
Exceptional! 5/5
(4 reviews)
avg/night
  • 3 BR
  • 2 BA
  • Sleeps 8
Cottage #883977vb
4
Viewed 13 times in the last 48 hours
  • 1 BR
  • 1 BA
  • 1 HF BA
  • Sleeps 4
Apartment #844031vb
8
Wonderful! 4.8/5
(14 reviews)
avg/night
  • 4 BR
  • 3 BA
  • Sleeps 12
House #3786046
14
Viewed 6 times in the last 48 hours
Excellent! 4.7/5
(19 reviews)
avg/night
  • 4 BR
  • 2 BA
  • Sleeps 10
House #704799vb
19
Viewed 10 times in the last 48 hours
  • 3 BR
  • 2 BA
  • Sleeps 9
Apartment #409821vb
10
Excellent! 4.7/5
(14 reviews)
avg/night
  • 6 BR
  • 2 BA
  • Sleeps 11
House #235930
14
Viewed 10 times in the last 48 hours
Exceptional! 5/5
(40 reviews)
avg/night
  • 4 BR
  • 4 BA
  • 1 HF BA
  • Sleeps 13
House #356548vb
40
Viewed 11 times in the last 48 hours
Exceptional! 5/5
(17 reviews)
avg/night
  • 3 BR
  • 2 BA
  • 1 HF BA
  • Sleeps 8
Cottage #503705vb
17
  • 4 BR
  • 2 BA
  • Sleeps 10
House #398147vb
12
Excellent! 4.7/5
(29 reviews)
avg/night
  • 3 BR
  • 1 BA
  • 1 HF BA
  • Sleeps 7
House #429782vb
29
Viewed 10 times in the last 48 hours
Wonderful! 4.8/5
(25 reviews)
avg/night
  • 2 BR
  • 1 BA
  • 1 HF BA
  • Sleeps 6
House #431733vb
25
Viewed 17 times in the last 48 hours
Excellent! 4.6/5
(31 reviews)
avg/night
  • 3 BR
  • 2 BA
  • Sleeps 12
House #7002752
31
Viewed 13 times in the last 48 hours
Wonderful! 4.9/5
(10 reviews)
avg/night
  • 3 BR
  • 1 BA
  • 1 HF BA
  • Sleeps 8
House #571411vb
10
Viewed 6 times in the last 48 hours
Wonderful! 4.9/5
(31 reviews)
avg/night
  • 1 BR
  • 1 BA
  • Sleeps 5
Apartment #494798vb
31
Viewed 15 times in the last 48 hours
  • 3 BR
  • 2 BA
  • 1 HF BA
  • Sleeps 8
House #797359vb
6
Wonderful! 4.9/5
(12 reviews)
avg/night
  • 4 BR
  • 2 BA
  • Sleeps 8
Estate #730130vb
12
Viewed 13 times in the last 48 hours
Wonderful! 4.9/5
(9 reviews)
avg/night
  • 5 BR
  • 2 BA
  • Sleeps 10
Farmhouse #582873vb
9
Viewed 15 times in the last 48 hours
  • 4 BR
  • 2 BA
  • Sleeps 10
Farmhouse #598989vb
2
Viewed 9 times in the last 48 hours
  • 1 BR
  • 1 BA
  • Sleeps 3
Apartment #589368vb
4
  • 2 BR
  • 1 BA
  • Sleeps 4
Chateau / Country House #738311vb
5
avg/night
  • 3 BR
  • 1 BA
  • Sleeps 8
House #440251vb
1
Viewed 7 times in the last 48 hours
  • 4 BR
  • 2 BA
  • Sleeps 8
House #3917327
1
Viewed 8 times in the last 48 hours
  • 3 BR
  • 2 BA
  • Sleeps 9
House #706116vb
9
Wonderful! 4.9/5
(18 reviews)
avg/night
  • 2 BR
  • 1 BA
  • Sleeps 6
House #53282vb
18
Viewed 11 times in the last 48 hours
Wonderful! 4.8/5
(22 reviews)
avg/night
  • 3 BR
  • 1 BA
  • Sleeps 6
Cottage #418738vb
22
Viewed 20 times in the last 48 hours
Wonderful! 4.8/5
(18 reviews)
avg/night
  • 4 BR
  • 4 BA
  • 1 HF BA
  • Sleeps 10
Estate #606821vb
18
Viewed 20 times in the last 48 hours
  • 4 BR
  • 3 BA
  • 1 HF BA
  • Sleeps 8
House #458295vb
8
  • 2 BR
  • 1 BA
  • Sleeps 5
House #4112420
1
  • 3 BR
  • 1 BA
  • Sleeps 8
House #4204088
1
avg/night
  • 8 BR
  • 8 BA
  • Sleeps 4
Hotel #4093884
Viewed 7 times in the last 48 hours
Exceptional! 5/5
(9 reviews)
avg/night
  • 2 BR
  • 1 BA
  • 1 HF BA
  • Sleeps 4
House #473897vb
9
  • 3 BR
  • 2 BA
  • 1 HF BA
  • Sleeps 8
House #565548vb
3
Wonderful! 4.8/5
(19 reviews)
avg/night
  • 4 BR
  • 2 BA
  • Sleeps 12
House #395841vb
19
Viewed 9 times in the last 48 hours
  • 5 BR
  • 5 BA
  • 1 HF BA
  • Sleeps 10
House #600779vb
3
  • 4 BR
  • 2 BA
  • 1 HF BA
  • Sleeps 11
House #592542vb
  • 4 BR
  • 4 BA
  • Sleeps 10
House #732410vb
  • 4 BR
  • 4 BA
  • Sleeps 8
House #4176971
  • 6 BR
  • 4 BA
  • Sleeps 14
Estate #4200107
1
avg/night
  • 1 BR
  • 1 BA
  • Sleeps 10
Recreational Vehicle #4243662
Viewed 25 times in the last 48 hours
avg/night
  • 3 BR
  • 1 BA
  • Sleeps 6
House #4247910
Viewed 7 times in the last 48 hours
  • 6 BR
  • 4 BA
  • 1 HF BA
  • Sleeps 11
Estate #1015635vb
Viewed 8 times in the last 48 hours
  • 2 BR
  • 1 BA
  • Sleeps 4
Apartment #1045032vb
Viewed 13 times in the last 48 hours
  • 1 - 50 of 63

Vacation Rentals in Chestertown, Maryland (63)