Search results; 343 homes in Chestertown

Top guest favourite
Home in Chestertown
NEW Chestertown Retreat
3 bedrooms, 4 beds, 1.5 bathrooms
17–22 Nov
,
4.97 out of 5 average rating, 60 reviews
Top guest favourite
Flat in Chestertown
Chestertown Private cottage with NFL Sun Ticket
1 king bed
30 Nov – 5 Dec
4.96 out of 5 average rating, 252 reviews
Top guest favourite
Guest suite in Chestertown
House On The Hill - Historic Private Second Floor
2 bedrooms3 beds,
15–20 Nov
4.99 out of 5 average rating, 110 reviews
Top guest favourite
Home in Chestertown
High Tide & Hound
2 bedrooms3 beds,
16–21 Nov
4.98 out of 5 average rating, 46 reviews
Home in Chestertown
Walk to Historic Chestertown: Dog-Friendly Retreat
2 bedrooms3 beds,
8–13 Dec
New place to stay
Top guest favourite
Home in Chestertown
Cozy 3-bedroom home w/ Hot tub & firepit
3 bedrooms3 queen beds,
14–19 Nov
4.97 out of 5 average rating, 151 reviews
Top guest favourite
Guest suite in Chestertown
Chestertown - Eastern Shore Getaway
1 bedroom2 beds,
15–20 Nov
4.98 out of 5 average rating, 181 reviews
Top guest favourite
Home in Chestertown
Historic home near town center with NFL Sun Ticket
5 bedrooms5 beds,
27 Nov – 2 Dec
5.0 out of 5 average rating, 217 reviews
Top guest favourite
Casa particular in Chestertown
Red, White & Waterview Studio Apt with pool
1 bedroom2 beds,
16–21 Nov
4.93 out of 5 average rating, 168 reviews
Top guest favourite
Home in Chestertown
2 Beds, 2.5 Baths - Perfect Downtown Location
2 bedrooms2 queen beds,
15–20 Nov
4.97 out of 5 average rating, 104 reviews
Top guest favourite
Guest suite in Chestertown
Beautiful Waterfront Chestertown Getaway
1 bedroom2 beds,
25 Feb – 2 Mar
4.99 out of 5 average rating, 240 reviews
Superhost
Guest house in Chestertown
Cozy Carriage House
1 queen bed
24–29 Nov
4.87 out of 5 average rating, 184 reviews
Top guest favourite
Flat in Chestertown
Bright, new apartment in the heart of Chestertown
2 bedrooms2 beds,
16–21 Nov
4.97 out of 5 average rating, 113 reviews
Top guest favourite
Home in Chestertown
Relaxing Waterfront - Golf Course & Sunset Views
3 bedrooms6 beds,
16–21 Nov
5.0 out of 5 average rating, 23 reviews
Top guest favourite
Home in Chestertown
Harbor View Haven | Waterfront w/ Hot Tub + Dock!
3 bedrooms6 beds,
14–19 Nov
4.96 out of 5 average rating, 91 reviews
Top guest favourite
Flat in Chestertown
Waterfront historic district 1BR Apartment
1 bedroom1 king bed,
14–19 Nov
5.0 out of 5 average rating, 129 reviews
Guest favourite
Home in Chestertown
Charming Haven on High
2 bedrooms3 beds,
17–22 Nov
4.93 out of 5 average rating, 45 reviews
Guest favourite
Room in Still Pond
House in Still Pond 3, Maryland
2 beds
14–19 Nov
4.76 out of 5 average rating, 34 reviews
Top guest favourite
Farm stay in Chestertown
Blue Heron Farm Waterfront Chalet
3 bedrooms4 beds,
16–21 Nov
4.94 out of 5 average rating, 174 reviews