208 places

Guest favorite
Guest suite in Chestertown
Beautiful Waterfront Chestertown Getaway
2 beds
Jun 24 – 29
4.99 out of 5 average rating, 191 reviews
Superhost
Guesthouse in Chestertown
Cozy Carriage House
1 queen bed
Apr 29 – May 4
4.88 out of 5 average rating, 156 reviews
Guest favorite
Farm stay in Centreville
3 bedroom home with pool and game room
4 beds
Apr 27 – May 2
4.96 out of 5 average rating, 51 reviews
Guest favorite
Home in Chestertown
River front cottage with private dock & water fun
11 beds
Apr 19 – 24
5.0 out of 5 average rating, 75 reviews
Guest favorite
Home in Rock Hall
Chesapeake Bay Retreat w/ Views!
4 beds
May 12 – 17
5.0 out of 5 average rating, 16 reviews
Guest favorite
Farm stay in Chestertown
Outrange at Blue Heron Farm
Apr 19 – 24
4.94 out of 5 average rating, 107 reviews
Guest favorite
Home in Chestertown
Simple Living on the Pond
2 queen beds
Apr 29 – May 4
4.93 out of 5 average rating, 73 reviews
Guest favorite
Apartment in Chestertown
Waterfront historic district 1BR Apartment
1 king bed
Apr 28 – May 3
5.0 out of 5 average rating, 67 reviews
Guest favorite
Farm stay in Centreville
Farm Stay at Lansdowne Manor
7 beds
Apr 24 – 29
5.0 out of 5 average rating, 22 reviews
Guest favorite
Home in Chestertown
Cozy 3-bedroom home w/ screened in porch & firepit
3 queen beds
Apr 30 – May 5
4.96 out of 5 average rating, 71 reviews
Guest favorite
Home in Chestertown
2 Beds, 2.5 Baths, Perfect Downtown Location
2 queen beds
Apr 28 – May 3
4.98 out of 5 average rating, 41 reviews
Guest favorite
Home in Millington
The Peaceful Getaway (with private pool & hot tub)
3 beds
Apr 22 – 27
4.91 out of 5 average rating, 34 reviews
Guest favorite
Home in Chestertown
Pet friendly, historic house, near town center.
6 beds
Jun 16 – 21
5.0 out of 5 average rating, 154 reviews
Guest favorite
Home in Chestertown
Waterfront Paradise w/ Pier - kayak to Chestertown
7 beds
Apr 28 – May 3
4.91 out of 5 average rating, 22 reviews
Guest favorite
Guesthouse in Chestertown
Piney Grove 2 Bedroom Carriage House Apartment
3 beds
Apr 27 – May 2
4.97 out of 5 average rating, 33 reviews
Guest favorite
Home in Chestertown
Heron Creek
5 beds
Apr 19 – 24
5.0 out of 5 average rating, 8 reviews
Guest favorite
Farm stay in Chestertown
Piney Grove Farm
5 beds
Apr 28 – May 3
4.97 out of 5 average rating, 86 reviews
Guest favorite
Home in Chestertown
Harbor View Haven | Waterfront w/ HOT TUB + Dock!
6 beds
May 9 – 14
4.93 out of 5 average rating, 30 reviews