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Search results; 213 places
213 places
Guest favorite
Guest favorite
Guest suite in Chestertown
Beautiful Waterfront Chestertown Getaway
2 beds
2 beds
Jun 24 – 29
Jun 24 – 29
$130
night
$130 per night
4.99 out of 5 average rating, 191 reviews
4.99 (191)
Guest favorite
Guest favorite
Home in Chestertown
River front cottage with private dock & water fun
11 beds
11 beds
Apr 19 – 24
Apr 19 – 24
$450
night
$450 per night
5.0 out of 5 average rating, 75 reviews
5.0 (75)
Guest favorite
Guest favorite
Home in Rock Hall
Chesapeake Bay Retreat w/ Views!
4 beds
4 beds
May 12 – 17
May 12 – 17
$250
$139
night
$139 per night, originally $250
5.0 out of 5 average rating, 16 reviews
5.0 (16)
Guest favorite
Guest favorite
Home in Chestertown
Simple Living on the Pond
2 queen beds
2 queen beds
Apr 29 – May 4
Apr 29 – May 4
$107
night
$107 per night
4.93 out of 5 average rating, 73 reviews
4.93 (73)
Guest favorite
Guest favorite
Farm stay in Centreville
Farm Stay at Lansdowne Manor
7 beds
7 beds
Apr 24 – 29
Apr 24 – 29
$284
night
$284 per night
5.0 out of 5 average rating, 22 reviews
5.0 (22)
Guest favorite
Guest favorite
Farm stay in Centreville
3 bedroom home with pool and game room
4 beds
4 beds
Apr 27 – May 2
Apr 27 – May 2
$200
night
$200 per night
4.96 out of 5 average rating, 51 reviews
4.96 (51)
Guest favorite
Guest favorite
Home in Chestertown
Cozy 3-bedroom home w/ screened in porch & firepit
3 queen beds
3 queen beds
Apr 19 – 24
Apr 19 – 24
$219
$184
night
$184 per night, originally $219
4.96 out of 5 average rating, 71 reviews
4.96 (71)
Guest favorite
Guest favorite
Home in Millington
The Peaceful Getaway (with private pool & hot tub)
3 beds
3 beds
Apr 22 – 27
Apr 22 – 27
$199
night
$199 per night
4.91 out of 5 average rating, 34 reviews
4.91 (34)
Guest favorite
Guest favorite
Apartment in Chestertown
Waterfront historic district 1BR Apartment
1 king bed
1 king bed
Apr 28 – May 3
Apr 28 – May 3
$149
night
$149 per night
5.0 out of 5 average rating, 67 reviews
5.0 (67)
Guest favorite
Guest favorite
Home in Chestertown
2 Beds, 2.5 Baths, Perfect Downtown Location
2 queen beds
2 queen beds
Apr 28 – May 3
Apr 28 – May 3
$181
night
$181 per night
4.98 out of 5 average rating, 41 reviews
4.98 (41)
Guest favorite
Guest favorite
Home in Chestertown
Pet friendly, historic house, near town center.
6 beds
6 beds
Jun 16 – 21
Jun 16 – 21
$289
night
$289 per night
5.0 out of 5 average rating, 154 reviews
5.0 (154)
Guest favorite
Guest favorite
Farm stay in Chestertown
Outrange at Blue Heron Farm
Apr 19 – 24
Apr 19 – 24
$214
night
$214 per night
4.94 out of 5 average rating, 107 reviews
4.94 (107)
Guest favorite
Guest favorite
Home in Chestertown
Heron Creek
5 beds
5 beds
Apr 19 – 24
Apr 19 – 24
$393
night
$393 per night
5.0 out of 5 average rating, 8 reviews
5.0 (8)
Guest favorite
Guest favorite
Guesthouse in Chestertown
Piney Grove 2 Bedroom Carriage House Apartment
3 beds
3 beds
Apr 27 – May 2
Apr 27 – May 2
$250
night
$250 per night
4.97 out of 5 average rating, 33 reviews
4.97 (33)
Guest favorite
Guest favorite
Home in Chestertown
Harbor View Haven | Waterfront w/ HOT TUB + Dock!
6 beds
6 beds
May 9 – 14
May 9 – 14
$392
night
$392 per night
4.93 out of 5 average rating, 30 reviews
4.93 (30)
Guest favorite
Guest favorite
Home in Chestertown
Waterfront Paradise w/ Pier - kayak to Chestertown
7 beds
7 beds
Apr 28 – May 3
Apr 28 – May 3
$465
night
$465 per night
4.91 out of 5 average rating, 22 reviews
4.91 (22)
Guest favorite
Guest favorite
Home in Church Hill
Private Peaceful Waterfront House w/ Pool, Hot Tub
12 beds
12 beds
Apr 19 – 24
Apr 19 – 24
$684
$499
night
$499 per night, originally $684
4.94 out of 5 average rating, 47 reviews
4.94 (47)
Guest favorite
Guest favorite
Home in Chestertown
Duchess of Kent: Walk to downtown & College
8 beds
8 beds
Apr 21 – 26
Apr 21 – 26
$346
night
$346 per night
4.99 out of 5 average rating, 148 reviews
4.99 (148)
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