Verified Review icon check navigate-up navigate-left navigate-right expand mail svg-lightning svg-24hr svg-house svg-sleeps svg-bedrooms svg-bathrooms svg-stay svg-toilet calendar svg-report-flag pet-dog svg-multiunit Default Owner Icon heart-filled Family icon
Cancel Clear Filters Apply Filters
More Filters

Price Per Night

$ $

Bedrooms

Bathrooms

Booking Options

Property Type

Location Type

Even More Filters

Features

Managed By

Clear Filters
Use filters to narrow your search results!
Viewed 5 times in the last 48 hours
  • Studio Guest House
  • 1 BA
  • 1400 sq. ft.
$83
avg/night
Viewed 11 times in the last 48 hours
  • 3 BR House
  • 2 BA
  • 1 HF BA
Exceptional! 5/5
(5 reviews)
avg/night
5
Viewed 10 times in the last 48 hours
  • 4 BR House
  • 3 BA
  • 2100 sq. ft.
Exceptional! 5/5
(7 reviews)
avg/night
7
Viewed 16 times in the last 48 hours
  • 4 BR House
  • 2 BA
  • 1 HF BA
Exceptional! 5/5
(6 reviews)
avg/night
6
  • 3 BR House
  • 1 BA
  • 1800 sq. ft.
avg/night
1
Viewed 17 times in the last 48 hours
  • 2 BR House
  • 1 BA
avg/night
2
  • 3 BR House
  • 2 BA
Exceptional! 5/5
(10 reviews)
avg/night
10
  • 1 BR Bed And Breakfast
  • 1 BA
avg/night
Viewed 38 times in the last 48 hours
  • 3 BR Cottage
  • 2 BA
  • 1435 sq. ft.
Exceptional! 5/5
(25 reviews)
avg/night
Premier Partner
25
Viewed 28 times in the last 48 hours
  • 3 BR House
  • 1 BA
  • 1 HF BA
Excellent! 4.6/5
(39 reviews)
avg/night
39
Viewed 37 times in the last 48 hours
  • 4 BR House
  • 2 BA
  • 2000 sq. ft.
Excellent! 4.6/5
(10 reviews)
avg/night
Premier Partner
10
Viewed 26 times in the last 48 hours
  • 4 BR House
  • 2 BA
Exceptional! 5/5
(21 reviews)
avg/night
21
Viewed 10 times in the last 48 hours
  • 1 BR Apartment
  • 1 BA
  • 650 sq. ft.
Wonderful! 4.9/5
(36 reviews)
avg/night
36
Viewed 49 times in the last 48 hours
  • 4 BR House
  • 2 BA
Excellent! 4.7/5
(27 reviews)
avg/night
27
Viewed 7 times in the last 48 hours
  • 3 BR House
  • 1 BA
  • 1 HF BA
  • 1150 sq. ft.
Wonderful! 4.8/5
(13 reviews)
avg/night
13
Viewed 11 times in the last 48 hours
  • 4 BR Cottage
  • 2 BA
Wonderful! 4.9/5
(22 reviews)
avg/night
22
Viewed 12 times in the last 48 hours
  • 3 BR Cottage
  • 1 BA
  • 1200 sq. ft.
Wonderful! 4.8/5
(26 reviews)
avg/night
26
Viewed 19 times in the last 48 hours
  • 2 BR Cottage
  • 2 BA
  • 1000 sq. ft.
Exceptional! 5/5
(30 reviews)
avg/night
30
Viewed 11 times in the last 48 hours
  • 3 BR House
  • 3 BA
  • 2000 sq. ft.
Exceptional! 5/5
(77 reviews)
avg/night
Premier Partner
77
Viewed 14 times in the last 48 hours
  • 3 BR House
  • 1 BA
Very Good! 4/5
(5 reviews)
avg/night
5
Viewed 8 times in the last 48 hours
  • 2 BR House
  • 1 BA
  • 1 HF BA
  • 1500 sq. ft.
Wonderful! 4.8/5
(32 reviews)
avg/night
32
  • 2 BR House
  • 1 BA
  • 1200 sq. ft.
$36
avg/night
Viewed 82 times in the last 48 hours
  • 6 BR House
  • 2 BA
  • 1700 sq. ft.
Excellent! 4.7/5
(19 reviews)
avg/night
19
Viewed 10 times in the last 48 hours
  • 1 BR House
  • 1 BA
  • 200 sq. ft.
$48
avg/night
Viewed 39 times in the last 48 hours
  • 5 BR House
  • 5 BA
  • 1 HF BA
  • 10021 sq. ft.
Wonderful! 4.8/5
(31 reviews)
avg/night
31
Viewed 18 times in the last 48 hours
  • 4 BR Estate
  • 4 BA
  • 1 HF BA
  • 5500 sq. ft.
Wonderful! 4.8/5
(22 reviews)
avg/night
22
  • 2 BR Apartment
  • 1 BA
  • 1 HF BA
avg/night
Viewed 9 times in the last 48 hours
  • 2 BR Apartment
  • 1 BA
Exceptional! 5/5
(9 reviews)
avg/night
9
  • 2 BR House
  • 1 BA
avg/night
  • 1 BR House
  • 1 BA
avg/night
1
Viewed 5 times in the last 48 hours
  • 4 BR House
  • 3 BA
  • 1 HF BA
  • 4200 sq. ft.
Wonderful! 4.9/5
(10 reviews)
avg/night
10
Viewed 10 times in the last 48 hours
  • 3 BR House
  • 1 BA
$97
avg/night
  • 3 BR House
  • 1 BA
avg/night
1
  • 2 BR House
  • 1 BA
  • 1000 sq. ft.
Wonderful! 4.9/5
(20 reviews)
avg/night
20
  • 2 BR Cottage
  • 1 BA
  • 1 HF BA
  • 1200 sq. ft.
avg/night
2
Viewed 9 times in the last 48 hours
  • 1 BR House
  • 1 BA
$60
avg/night
  • 2 BR Hotel
  • 1 BA
$82
avg/night
  • 2 BR Guest House
  • 1 BA
avg/night
Viewed 19 times in the last 48 hours
  • 5 BR House
  • 2 BA
avg/night
1
Viewed 17 times in the last 48 hours
  • 6 BR Estate
  • 4 BA
  • 5000 sq. ft.
avg/night
1
Viewed 10 times in the last 48 hours
  • 7 BR House
  • 4 BA
  • 1 HF BA
  • 10000 sq. ft.
Exceptional! 5/5
(9 reviews)
avg/night
9
Viewed 7 times in the last 48 hours
  • 1 BR House
  • 1 BA
  • 200 sq. ft.
$50
avg/night
Viewed 13 times in the last 48 hours
  • 5 BR House
  • 4 BA
  • 1 HF BA
avg/night
2
Viewed 14 times in the last 48 hours
  • 6 BR Estate
  • 4 BA
  • 1 HF BA
  • 6000 sq. ft.
avg/night
Viewed 10 times in the last 48 hours
  • 2 BR House
  • 1 BA
avg/night
  • 5 BR House
  • 5 BA
  • 1 HF BA
  • 4000 sq. ft.
avg/night
3
Viewed 7 times in the last 48 hours
  • 1 BR Recreational Vehicle
  • 1 BA
$43
avg/night
Viewed 8 times in the last 48 hours
  • 4 BR House
  • 4 BA
  • 1 HF BA
Exceptional! 5/5
(42 reviews)
avg/night
42
Viewed 14 times in the last 48 hours
  • 5 BR House
  • 3 BA
  • 1 HF BA
avg/night
2
Viewed 21 times in the last 48 hours
  • 11 BR Estate
  • 8 BA
  • 1 HF BA
  • 10000 sq. ft.
avg/night
1
 

Recent Chestertown Reviews

Perfect Weekend Getaway!

5 of 5
A perfect small family getaway to celebrate a 5 year old’s birthday! Game room and pool were a huge hit. The house was stunning, definitely worthy of a repeat stay. Plenty of room for everyone to have their own space! Thanks again for memories that will be talked about for quite some time.
  • Submitted: Feb 19, 2018
  • Stayed: Feb 2018

We love it here!

5 of 5
Great house and property for a relaxing time by the water. We highly recommend booking a stay here!
  • Submitted: Feb 15, 2018
  • Stayed: Feb 2018