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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)
$89
avg/night
  • 1 BR
  • 1 BA
  • Sleeps 6
Condo #3896538ha
16
Viewed 28 times in the last 48 hours
Wonderful! 4.8/5
(15 reviews)
avg/night
  • 2 BR
  • 1 BA
  • Sleeps 6
Condo #716031
15
Viewed 49 times in the last 48 hours
Wonderful! 4.8/5
(13 reviews)
avg/night
  • 4 BR
  • 2 BA
  • Sleeps 12
House #4240841ha
13
Viewed 35 times in the last 48 hours
Excellent! 4.3/5
(8 reviews)
avg/night
  • 2 BR
  • 1 BA
  • Sleeps 5
Condo #3804012ha
8
Viewed 18 times in the last 48 hours
Excellent! 4.3/5
(18 reviews)
avg/night
  • 2 BR
  • 1 BA
  • Sleeps 6
Cabin #3014265ha
18
Viewed 72 times in the last 48 hours
Wonderful! 4.9/5
(16 reviews)
avg/night
  • 2 BR
  • 2 BA
  • Sleeps 4
House #4044539ha
16
Viewed 33 times in the last 48 hours
Very Good! 4/5
(10 reviews)
avg/night
  • 3 BR
  • 3 BA
  • Sleeps 6
Condo #4014526ha
10
Viewed 47 times in the last 48 hours
Wonderful! 4.9/5
(10 reviews)
avg/night
  • 3 BR
  • 3 BA
  • Sleeps 8
Cottage #175549ha
10
Viewed 16 times in the last 48 hours
Exceptional! 5/5
(7 reviews)
avg/night
  • 3 BR
  • 3 BA
  • Sleeps 7
Townhome #689905
7
Exceptional! 5/5
(6 reviews)
avg/night
  • 3 BR
  • 2 BA
  • Sleeps 10
House #3924952ha
6
Viewed 15 times in the last 48 hours
Very Good! 4/5
(6 reviews)
avg/night
  • 2 BR
  • 1 BA
  • Sleeps 5
Cabin #3016070ha
6
Viewed 42 times in the last 48 hours
  • 3 BR
  • 2 BA
  • Sleeps 9
House #4313390ha
3
Viewed 21 times in the last 48 hours
Wonderful! 4.9/5
(19 reviews)
avg/night
  • 3 BR
  • 2 BA
  • Sleeps 8
House #4073769ha
19
Viewed 12 times in the last 48 hours
Wonderful! 4.8/5
(21 reviews)
avg/night
  • 3 BR
  • 1 BA
  • Sleeps 8
House #7080936ha
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 #3828287ha
9
Viewed 17 times in the last 48 hours
Exceptional! 5/5
(9 reviews)
avg/night
  • 4 BR
  • 1 BA
  • Sleeps 7
Cottage #3496194ha
9
Very Good! 4.2/5
(14 reviews)
avg/night
  • 6 BR
  • 3 BA
  • Sleeps 26
House #258920ha
14
Viewed 28 times in the last 48 hours
avg/night
  • 4 BR
  • 2 BA
  • Sleeps 8
Cottage #1020543
2
Viewed 26 times in the last 48 hours
  • 6 BR
  • 3 BA
  • Sleeps 12
House #557834
1
Viewed 13 times in the last 48 hours
avg/night
  • 7 BR
  • 4 BA
  • Sleeps 18
House #1034527
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 #641786
16
Viewed 17 times in the last 48 hours
avg/night
  • 2 BR
  • 2 BA
  • Sleeps 6
Cabin #4087680ha
Viewed 50 times in the last 48 hours
  • 2 BR
  • 1 BA
  • 1 HF BA
  • Sleeps 7
Condo #1036429
Viewed 42 times in the last 48 hours
avg/night
  • 4 BR
  • 2 BA
  • 1 HF BA
  • Sleeps 8
Chalet #593993
Viewed 9 times in the last 48 hours
  • 6 BR
  • 2 BA
  • Sleeps 11
Lodge #3727616ha
1
Viewed 25 times in the last 48 hours
avg/night
  • 4 BR
  • 2 BA
  • Sleeps 13
House #948569
Viewed 11 times in the last 48 hours
avg/night
  • 2 BR
  • 1 BA
  • Sleeps 8
Cottage #4473478ha
1
Viewed 13 times in the last 48 hours
Exceptional! 5/5
(31 reviews)
avg/night
  • 3 BR
  • 2 BA
  • Sleeps 9
Chalet #3348
31
Viewed 11 times in the last 48 hours
avg/night
  • 3 BR
  • 2 BA
  • Sleeps 9
House #4479049ha
Viewed 16 times in the last 48 hours
$89
avg/night
  • 2 BR
  • 1 BA
  • Sleeps 6
Apartment #948565
3
Viewed 9 times in the last 48 hours
avg/night
  • 1 BR
  • 1 BA
  • Sleeps 2
Cabin #1021229
Viewed 8 times in the last 48 hours
avg/night
  • 1 BR
  • 1 BA
  • Sleeps 4
Cabin #4537664ha
1
Viewed 20 times in the last 48 hours
avg/night
  • 3 BR
  • 1 BA
  • Sleeps 6
Cabin #740351
4
Viewed 8 times in the last 48 hours
  • 5 BR
  • 2 BA
  • Sleeps 8
House #239560ha
Viewed 7 times in the last 48 hours
avg/night
  • 4 BR
  • 1 BA
  • Sleeps 7
Cottage #3667204ha
1
Viewed 7 times in the last 48 hours
avg/night
  • 4 BR
  • 4 BA
  • 1 HF BA
  • Sleeps 16
Apartment #3726412ha
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 #179508ha
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 #3001286ha
105
Viewed 121 times in the last 48 hours
Wonderful! 4.8/5
(12 reviews)
avg/night
  • 3 BR
  • 2 BA
  • Sleeps 7
House #863326
12
Viewed 126 times in the last 48 hours
Wonderful! 4.9/5
(12 reviews)
avg/night
  • 2 BR
  • 1 BA
  • Sleeps 6
Cabin #802195
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 #3876403ha
38
Viewed 47 times in the last 48 hours
Excellent! 4.4/5
(14 reviews)
avg/night
  • 2 BR
  • 1 BA
  • Sleeps 4
Cabin #7006524ha
14
Viewed 54 times in the last 48 hours
Exceptional! 5/5
(26 reviews)
avg/night
  • 2 BR
  • 1 BA
  • Sleeps 6
Cottage #3678055ha
26
Viewed 10 times in the last 48 hours
Wonderful! 4.9/5
(17 reviews)
avg/night
  • 1 BR
  • 1 BA
  • Sleeps 2
Cabin #4066619ha
17
Viewed 17 times in the last 48 hours
Wonderful! 4.9/5
(49 reviews)
avg/night
  • 3 BR
  • 2 BA
  • Sleeps 10
House #423420
49
Viewed 81 times in the last 48 hours
Exceptional! 5/5
(42 reviews)
avg/night
  • 6 BR
  • 4 BA
  • Sleeps 19
House #3858756ha
42
Viewed 28 times in the last 48 hours
Excellent! 4.3/5
(10 reviews)
avg/night
  • 2 BR
  • 1 BA
  • Sleeps 5
Cottage #3953323ha
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 #145704ha
11
Viewed 103 times in the last 48 hours
Exceptional! 5/5
(16 reviews)
avg/night
  • 3 BR
  • 2 BA
  • Sleeps 8
Cabin #976461ha
16
Viewed 115 times in the last 48 hours
Wonderful! 4.8/5
(20 reviews)
avg/night
  • 5 BR
  • 3 BA
  • Sleeps 12
House #189443ha
20
Viewed 86 times in the last 48 hours
  • 1 - 50 of 300+
 

Recent Chestertown Reviews

Great stay!

5 of 5
Nice quiet home. Perfect distance to everything we wanted to do while still being in our isolated retreat.
  • Submitted: Jun 25, 2017
  • Stayed: Jun 2017

Beautiful house in a gorgeous nature setting!

5 of 5
Tripp Lake Retreat was the perfect choice for our weekend getaway. I am kind of a perfectionist, so I actually browsed through atleast 20 other properties before settling on this one, and it was the best decision. We were 7 friends in the age range of 30-36, looking for a peaceful weekend getaway to just relax and have a good time. Tripp Lake Retreat provided just that. The house came with all the amenities and the kitchen was loaded with all that we needed to cook every day. We mostly grilled outside and sat on the deck to enjoy the sound of birds and beautiful views. The house has a large wrap around deck which is perfect to sit out and relax. Debby was a warm and kind host who made sure we had everything we needed to have a comfortable stay. The house is private, surrounded with trees and in the front a very short walk away is the lake which was great for boating and fishing. There is also a small golf course close by, but we didn't have the time to play. Easily a 5*!
  • Submitted: Jun 23, 2017
  • Stayed: Jun 2017