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Display total before taxes

Search results; 371 places in Chestertown

Guest favorite
Apartment in Chestertown
Quiet escape in center of town
1 king bed
Apr 7 – 12
4.97 out of 5 average rating, 187 reviews
Guest favorite
Home in Chestertown
Cozy 3-bedroom home w/ screened in porch & firepit
3 queen beds
Apr 8 – 13
4.96 out of 5 average rating, 69 reviews
Superhost
Guesthouse in Chestertown
Cozy Carriage House
1 queen bed
Apr 1 – 6
4.88 out of 5 average rating, 156 reviews
Guest favorite
Home in Chestertown
Historic house, near town center, pet friendly
6 beds
Apr 8 – 13
5.0 out of 5 average rating, 150 reviews
Guest favorite
Apartment in Chestertown
Waterfront historic district 1BR Apartment
1 king bed
Apr 8 – 13
5.0 out of 5 average rating, 64 reviews
Guest favorite
Casa particular in Chestertown
Red, White & Waterview Studio Apt with pool
2 beds
Apr 7 – 12
4.93 out of 5 average rating, 99 reviews
Guest favorite
Home in Chestertown
Beautifully remodeled home in Historic Chestertown
3 beds
Apr 1 – 6
4.88 out of 5 average rating, 25 reviews
Guest favorite
Apartment in Chestertown
Bright, new apartment in the heart of Chestertown
2 beds
Apr 7 – 12
5.0 out of 5 average rating, 44 reviews
Guest favorite
Home in Chestertown
Simple Living on the Pond
2 queen beds
Apr 6 – 11
4.93 out of 5 average rating, 69 reviews
Guest favorite
Home in Chestertown
2 Beds, 2.5 Baths, Perfect Downtown Location
2 queen beds
Apr 7 – 12
4.98 out of 5 average rating, 40 reviews
Guest favorite
Home in Chestertown
In Town Chestertown Rancher (1 Block to College)
5 beds
Apr 1 – 6
5.0 out of 5 average rating, 19 reviews
Guest favorite
Home in Chestertown
125 High - Luxury Historical Brick Victorian
2 beds
Apr 1 – 6
5.0 out of 5 average rating, 23 reviews
Guest favorite
Guest suite in Chestertown
Historic Downtown Garden Oasis with Private Patio
1 queen bed
Apr 20 – 25
4.93 out of 5 average rating, 45 reviews
Guest favorite
Home in Chestertown
Classic Victorian in Chestertown
7 beds
Apr 1 – 6
4.94 out of 5 average rating, 101 reviews
Guest favorite
Home in Chestertown
Duchess of Kent: Walk to downtown & College
8 beds
Apr 7 – 12
4.99 out of 5 average rating, 148 reviews
Guest favorite
Cabin in Chestertown
Rivershore Retreat
3 beds
Apr 1 – 6
4.98 out of 5 average rating, 215 reviews
Guest favorite
Home in Chestertown
Magnolia House ~Historic Downtown w/Private Garden
4 beds
Apr 1 – 6
5.0 out of 5 average rating, 23 reviews
Guest favorite
Home in Chestertown
The Patriot House-Chestertown, MD
7 beds
Apr 1 – 6
4.99 out of 5 average rating, 68 reviews