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Chestertown
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Search results; 371 places in Chestertown
371 places in Chestertown
Guest favorite
Guest favorite
Apartment in Chestertown
Quiet escape in center of town
1 king bed
1 king bed
Apr 7 – 12
Apr 7 – 12
$147
night
$147 per night
4.97 out of 5 average rating, 187 reviews
4.97 (187)
Guest favorite
Guest favorite
Home in Chestertown
Cozy 3-bedroom home w/ screened in porch & firepit
3 queen beds
3 queen beds
Apr 8 – 13
Apr 8 – 13
$207
night
$207 per night
4.96 out of 5 average rating, 69 reviews
4.96 (69)
Superhost
Superhost
Guesthouse in Chestertown
Cozy Carriage House
1 queen bed
1 queen bed
Apr 1 – 6
Apr 1 – 6
$100
night
$100 per night
4.88 out of 5 average rating, 156 reviews
4.88 (156)
Guest favorite
Guest favorite
Home in Chestertown
Historic house, near town center, pet friendly
6 beds
6 beds
Apr 8 – 13
Apr 8 – 13
$251
night
$251 per night
5.0 out of 5 average rating, 150 reviews
5.0 (150)
Guest favorite
Guest favorite
Apartment in Chestertown
Waterfront historic district 1BR Apartment
1 king bed
1 king bed
Apr 8 – 13
Apr 8 – 13
$154
night
$154 per night
5.0 out of 5 average rating, 64 reviews
5.0 (64)
Guest favorite
Guest favorite
Casa particular in Chestertown
Red, White & Waterview Studio Apt with pool
2 beds
2 beds
Apr 7 – 12
Apr 7 – 12
$100
night
$100 per night
4.93 out of 5 average rating, 99 reviews
4.93 (99)
Guest favorite
Guest favorite
Home in Chestertown
Beautifully remodeled home in Historic Chestertown
3 beds
3 beds
Apr 1 – 6
Apr 1 – 6
$189
night
$189 per night
4.88 out of 5 average rating, 25 reviews
4.88 (25)
Guest favorite
Guest favorite
Apartment in Chestertown
Bright, new apartment in the heart of Chestertown
2 beds
2 beds
Apr 7 – 12
Apr 7 – 12
$223
$186
night
$186 per night, originally $223
5.0 out of 5 average rating, 44 reviews
5.0 (44)
Guest favorite
Guest favorite
Home in Chestertown
Simple Living on the Pond
2 queen beds
2 queen beds
Apr 6 – 11
Apr 6 – 11
$107
night
$107 per night
4.93 out of 5 average rating, 69 reviews
4.93 (69)
Guest favorite
Guest favorite
Home in Chestertown
2 Beds, 2.5 Baths, Perfect Downtown Location
2 queen beds
2 queen beds
Apr 7 – 12
Apr 7 – 12
$181
night
$181 per night
4.98 out of 5 average rating, 40 reviews
4.98 (40)
Guest favorite
Guest favorite
Home in Chestertown
In Town Chestertown Rancher (1 Block to College)
5 beds
5 beds
Apr 1 – 6
Apr 1 – 6
$211
night
$211 per night
5.0 out of 5 average rating, 19 reviews
5.0 (19)
Guest favorite
Guest favorite
Home in Chestertown
125 High - Luxury Historical Brick Victorian
2 beds
2 beds
Apr 1 – 6
Apr 1 – 6
$299
night
$299 per night
5.0 out of 5 average rating, 23 reviews
5.0 (23)
Guest favorite
Guest favorite
Guest suite in Chestertown
Historic Downtown Garden Oasis with Private Patio
1 queen bed
1 queen bed
Apr 20 – 25
Apr 20 – 25
$154
night
$154 per night
4.93 out of 5 average rating, 45 reviews
4.93 (45)
Guest favorite
Guest favorite
Home in Chestertown
Classic Victorian in Chestertown
7 beds
7 beds
Apr 1 – 6
Apr 1 – 6
$193
night
$193 per night
4.94 out of 5 average rating, 101 reviews
4.94 (101)
Guest favorite
Guest favorite
Home in Chestertown
Duchess of Kent: Walk to downtown & College
8 beds
8 beds
Apr 7 – 12
Apr 7 – 12
$450
$346
night
$346 per night, originally $450
4.99 out of 5 average rating, 148 reviews
4.99 (148)
Guest favorite
Guest favorite
Cabin in Chestertown
Rivershore Retreat
3 beds
3 beds
Apr 1 – 6
Apr 1 – 6
$297
night
$297 per night
4.98 out of 5 average rating, 215 reviews
4.98 (215)
Guest favorite
Guest favorite
Home in Chestertown
Magnolia House ~Historic Downtown w/Private Garden
4 beds
4 beds
Apr 1 – 6
Apr 1 – 6
$327
$275
night
$275 per night, originally $327
5.0 out of 5 average rating, 23 reviews
5.0 (23)
Guest favorite
Guest favorite
Home in Chestertown
The Patriot House-Chestertown, MD
7 beds
7 beds
Apr 1 – 6
Apr 1 – 6
$360
night
$360 per night
4.99 out of 5 average rating, 68 reviews
4.99 (68)
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