Search results; 448 homes in Chestertown

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Guest favorite
Apartment in Chestertown
Waterfront historic district 1BR Apartment
2 guests1 bedroom1 bed1 bath
Aug 1 – 6
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Aug 1 – 6
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ﺩ.ﺇ3,750 for 5 nights

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Top guest favorite
Guest suite in Chestertown
Chestertown - Eastern Shore Getaway
2 beds
Aug 1 – 6
ﺩ.ﺇ2,695 for 5 nights
4.98 out of 5 average rating, 166 reviews
Guest favorite
Home in Chestertown
NEW Chestertown Retreat
4 beds
Aug 1 – 6
ﺩ.ﺇ3,875 for 5 nights
4.98 out of 5 average rating, 47 reviews
Top guest favorite
Apartment in Chestertown
Bright, new apartment in the heart of Chestertown
2 beds
Aug 1 – 6
ﺩ.ﺇ4,960 for 5 nights
4.98 out of 5 average rating, 98 reviews
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Guesthouse in Chestertown
Cozy Carriage House
1 queen bed
Aug 1 – 6
ﺩ.ﺇ2,842 for 5 nights
4.89 out of 5 average rating, 177 reviews
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Home in Chestertown
Charming Haven on High
3 beds
Aug 3 – 8
ﺩ.ﺇ3,983 for 5 nights
4.97 out of 5 average rating, 31 reviews
Top guest favorite
Apartment in Chestertown
Private cozy cottage - center of Chestertown .
1 king bed
Aug 10 – 15
ﺩ.ﺇ3,735 for 5 nights
4.96 out of 5 average rating, 241 reviews
Top guest favorite
Home in Chestertown
Cozy 3-bedroom home w/ Hot tub & firepit
3 queen beds
Aug 23 – 28
ﺩ.ﺇ4,503 for 5 nights
4.97 out of 5 average rating, 135 reviews
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Home in Chestertown
River Cottage, Chestertown
2 queen beds
Aug 1 – 6
ﺩ.ﺇ5,252 for 5 nights
4.94 out of 5 average rating, 31 reviews
Top guest favorite
Casa particular in Chestertown
Red, White & Waterview Studio Apt with pool
2 beds
Aug 4 – 9
ﺩ.ﺇ2,975 for 5 nights
4.92 out of 5 average rating, 154 reviews
Home in Centreville
Historic Centreville Home
3 beds
Aug 1 – 6
ﺩ.ﺇ3,707 for 5 nights
4.77 out of 5 average rating, 78 reviews
Guest favorite
Cottage in Centreville
Captain’s Quarters - Unique home on Corsica River!
2 beds
Aug 3 – 8
ﺩ.ﺇ3,983 for 5 nights
4.93 out of 5 average rating, 46 reviews
Top guest favorite
Guesthouse in Chestertown
Owl Cottage - Cozy, Private & Walkable to Town
2 beds
Sep 21 – 26
ﺩ.ﺇ4,284 for 5 nights
5.0 out of 5 average rating, 34 reviews
Guest favorite
Room in Chestertown
Stay with MartinProfessor,
Private Room w/bath: Walk to Washington College
Aug 1 – 6
ﺩ.ﺇ2,829 for 5 nights
4.96 out of 5 average rating, 50 reviews
Guest favorite
Home in Chestertown
River front cottage with private dock & water fun
11 beds
Sep 9 – 14
ﺩ.ﺇ10,375 for 5 nights
4.97 out of 5 average rating, 90 reviews
Top guest favorite
Home in Chestertown
Waterfront house with private dock & kayaks!
2 beds
Oct 6 – 11
ﺩ.ﺇ5,489 for 5 nights
5.0 out of 5 average rating, 62 reviews
Top guest favorite
Home in Chestertown
The Portside Manor - Queen Street Chestertown
4 beds
Aug 3 – 8
ﺩ.ﺇ8,524 for 5 nights
5.0 out of 5 average rating, 10 reviews
Top guest favorite
Home in Chestertown
In Town Chestertown Rancher (1 Block to College)
5 beds
Aug 4 – 9
ﺩ.ﺇ5,618 for 5 nights
5.0 out of 5 average rating, 44 reviews
Guest favorite
Townhouse in Chestertown
The Retreat in Historic Downtown Chestertown
3 beds
Aug 16 – 21
ﺩ.ﺇ5,532 for 5 nights
4.81 out of 5 average rating, 16 reviews