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Exceptional! 5/5
(7 reviews)
avg/night
  • 3 BR
  • 2 BA
  • Sleeps 6
House #759063vb
7
  • 4 BR
  • 3 BA
  • Sleeps 8
House #4487352
4
  • 4 BR
  • 2 BA
  • 1 HF BA
  • Sleeps 8
House #4558937
1
  • 4 BR
  • 3 BA
  • Sleeps 8
House #1054955vb
Exceptional! 5/5
(60 reviews)
avg/night
  • 3 BR
  • 3 BA
  • Sleeps 8
House #294688vb
60
Viewed 18 times in the last 48 hours
Wonderful! 4.9/5
(14 reviews)
avg/night
  • 1 BR
  • 1 BA
  • 1 HF BA
  • Sleeps 4
Apartment #844031vb
14
Viewed 8 times in the last 48 hours
Exceptional! 5/5
(10 reviews)
avg/night
  • 3 BR
  • 2 BA
  • Sleeps 8
Cottage #883977vb
10
Viewed 15 times in the last 48 hours
Wonderful! 4.8/5
(21 reviews)
avg/night
  • 4 BR
  • 3 BA
  • Sleeps 12
House #3786046
21
Viewed 16 times in the last 48 hours
Wonderful! 4.9/5
(26 reviews)
avg/night
  • 5 BR
  • 5 BA
  • 1 HF BA
  • Sleeps 10
House #3592853
26
Viewed 36 times in the last 48 hours
Wonderful! 4.8/5
(19 reviews)
avg/night
  • 5 BR
  • 4 BA
  • Sleeps 18
House #581725vb
19
Viewed 9 times in the last 48 hours
Wonderful! 4.9/5
(12 reviews)
avg/night
  • 3 BR
  • 2 BA
  • Sleeps 9
Apartment #409821vb
12
Viewed 19 times in the last 48 hours
Exceptional! 5/5
(25 reviews)
avg/night
  • 2 BR
  • 2 BA
  • Sleeps 5
Cottage #608459vb
25
Viewed 14 times in the last 48 hours
Exceptional! 5/5
(41 reviews)
View details for price
  • 4 BR
  • 4 BA
  • 1 HF BA
  • Sleeps 13
House #356548vb
41
Excellent! 4.7/5
(23 reviews)
avg/night
  • 4 BR
  • 2 BA
  • Sleeps 10
House #704799vb
23
Viewed 18 times in the last 48 hours
Excellent! 4.6/5
(34 reviews)
avg/night
  • 3 BR
  • 1 BA
  • 1 HF BA
  • Sleeps 7
House #429782vb
34
Exceptional! 5/5
(25 reviews)
avg/night
  • 3 BR
  • 2 BA
  • 1 HF BA
  • Sleeps 8
Cottage #503705vb
25
Viewed 7 times in the last 48 hours
Excellent! 4.6/5
(39 reviews)
avg/night
  • 3 BR
  • 3 BA
  • Sleeps 12
House #7002752
39
Viewed 26 times in the last 48 hours
Wonderful! 4.9/5
(19 reviews)
avg/night
  • 4 BR
  • 2 BA
  • Sleeps 10
House #398147vb
19
Viewed 10 times in the last 48 hours
Wonderful! 4.8/5
(16 reviews)
avg/night
  • 6 BR
  • 2 BA
  • Sleeps 11
House #235930
16
Viewed 12 times in the last 48 hours
Wonderful! 4.8/5
(11 reviews)
avg/night
  • 3 BR
  • 1 BA
  • 1 HF BA
  • Sleeps 8
House #571411vb
11
Viewed 6 times in the last 48 hours
Wonderful! 4.8/5
(6 reviews)
avg/night
  • 1 BR
  • 1 BA
  • Sleeps 5
Apartment #838035vb
6
Wonderful! 4.9/5
(15 reviews)
avg/night
  • 4 BR
  • 2 BA
  • Sleeps 8
Estate #730130vb
15
Viewed 23 times in the last 48 hours
  • 3 BR
  • 1 BA
  • Sleeps 8
House #440251vb
5
Wonderful! 4.9/5
(35 reviews)
avg/night
  • 1 BR
  • 1 BA
  • Sleeps 5
Apartment #494798vb
35
Viewed 49 times in the last 48 hours
Wonderful! 4.9/5
(8 reviews)
avg/night
  • 3 BR
  • 2 BA
  • 1 HF BA
  • Sleeps 8
House #797359vb
8
Viewed 18 times in the last 48 hours
  • 5 BR
  • 2 BA
  • Sleeps 10
Farmhouse #623923vb
5
Exceptional! 5/5
(6 reviews)
avg/night
  • 2 BR
  • 1 BA
  • Sleeps 4
Chateau / Country House #738311vb
6
Viewed 13 times in the last 48 hours
Wonderful! 4.8/5
(5 reviews)
avg/night
  • 1 BR
  • 1 BA
  • Sleeps 3
Apartment #589368vb
5
Viewed 5 times in the last 48 hours
Wonderful! 4.9/5
(9 reviews)
avg/night
  • 4 BR
  • 3 BA
  • 1 HF BA
  • Sleeps 8
House #458295vb
9
Viewed 7 times in the last 48 hours
Exceptional! 5/5
(5 reviews)
avg/night
  • 2 BR
  • 1 BA
  • Sleeps 4
Apartment #1045032vb
5
Viewed 7 times in the last 48 hours
Wonderful! 4.8/5
(20 reviews)
avg/night
  • 4 BR
  • 4 BA
  • 1 HF BA
  • Sleeps 10
Estate #606821vb
20
Viewed 7 times in the last 48 hours
Wonderful! 4.8/5
(31 reviews)
avg/night
  • 2 BR
  • 1 BA
  • 1 HF BA
  • Sleeps 6
House #431733vb
31
Viewed 7 times in the last 48 hours
  • 4 BR
  • 2 BA
  • Sleeps 10
Farmhouse #598989vb
3
  • 5 BR
  • 2 BA
  • Sleeps 10
Farmhouse #582873vb
11
  • 4 BR
  • 2 BA
  • Sleeps 8
House #3917327
3
Exceptional! 5/5
(7 reviews)
avg/night
  • 7 BR
  • 4 BA
  • 1 HF BA
  • Sleeps 13
House #935769vb
7
Wonderful! 4.9/5
(20 reviews)
avg/night
  • 2 BR
  • 1 BA
  • Sleeps 6
House #53282vb
20
Viewed 15 times in the last 48 hours
avg/night
  • 8 BR
  • 8 BA
  • Sleeps 4
Hotel #4093884
Viewed 8 times in the last 48 hours
avg/night
  • 5 BR
  • 4 BA
  • 1 HF BA
  • Sleeps 10
House #1089471vb
Viewed 5 times in the last 48 hours
Wonderful! 4.8/5
(24 reviews)
avg/night
  • 3 BR
  • 1 BA
  • Sleeps 6
Cottage #418738vb
24
Viewed 12 times in the last 48 hours
avg/night
  • 5 BR
  • 5 BA
  • 1 HF BA
  • Sleeps 10
House #600779vb
3
Viewed 5 times in the last 48 hours
  • 4 BR
  • 4 BA
  • Sleeps 8
House #410328vb
29
  • 2 BR
  • 1 BA
  • Sleeps 5
House #4112420
1
Viewed 14 times in the last 48 hours
  • 3 BR
  • 1 BA
  • Sleeps 8
House #4204088
1
Wonderful! 4.9/5
(20 reviews)
avg/night
  • 4 BR
  • 2 BA
  • Sleeps 8
Cottage #431105vb
20
Viewed 9 times in the last 48 hours
  • 2 BR
  • 1 BA
  • 1 HF BA
  • Sleeps 4
Cottage #1139912vb
1
Viewed 6 times in the last 48 hours
avg/night
  • 5 BR
  • 2 BA
  • Sleeps 10
House #4647406
1
Viewed 8 times in the last 48 hours
  • 2 BR
  • 1 BA
  • Sleeps 2
House #4533503
  • 6 BR
  • 4 BA
  • 1 HF BA
  • Sleeps 11
Estate #1015635vb
  • 4 BR
  • 2 BA
  • 1 HF BA
  • Sleeps 11
House #592542vb

Vacation Rentals in Chestertown, Maryland (65)