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Search Vacation Homes in Chestertown
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Compare 367 Vacation Homes in Chestertown with updated reviews, rates, and availability.
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
10.0 out of 10, Exceptional, (3)
The price is $629
$1,417 total
includes taxes & fees
Jun 4 - Jun 5
Caribbean Pool Home <1 mile from Matapeake Beach!
Caribbean Pool Home <1 mile from Matapeake Beach!
10.0 out of 10, Exceptional, (1)
The price is $253
$795 total
includes taxes & fees
May 28 - May 29
BAYSIDE BUNGALOW
BAYSIDE BUNGALOW
10.0 out of 10, Exceptional, (16)
The price is $175
$271 total
includes taxes & fees
May 17 - May 18
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Cozy and peaceful BASEMENT in a house, close to different restaurants and a park
Cozy and peaceful BASEMENT in a house, close to different restaurants and a park
10.0 out of 10, Exceptional, (4)
The price is $78
$121 total
includes taxes & fees
May 18 - May 19
Charming Historic Townhouse Steps From USNA
Charming Historic Townhouse Steps From USNA
10.0 out of 10, Exceptional, (12)
Hidden gem with water and golf course views! Bike ride to downtown!
Hidden gem with water and golf course views! Bike ride to downtown!
10.0 out of 10, Exceptional, (25)
Waterfront w/Deepwater Pier Walking Distance to Downtown Chestertown
Waterfront w/Deepwater Pier Walking Distance to Downtown Chestertown
10.0 out of 10, Exceptional, (84)
Directly Across from Gate One & Steps from the Waterfront
Directly Across from Gate One & Steps from the Waterfront
10.0 out of 10, Exceptional, (179)
Riverfront home with multiple decks, central AC, washer/dryer - two dogs OK
Riverfront home with multiple decks, central AC, washer/dryer - two dogs OK
10.0 out of 10, Exceptional, (31)
Grasonville Home w/ Private Pool on the Water
Grasonville Home w/ Private Pool on the Water
10.0 out of 10, Exceptional, (12)
Glen Burnie Escape - Pet friendly with easy access to multiple attractions.
Glen Burnie Escape - Pet friendly with easy access to multiple attractions.
10.0 out of 10, Exceptional, (3)
The price is $250
$325 total
includes taxes & fees
May 27 - May 28
Free parking Historic Union House Downtown with private patio
Free parking Historic Union House Downtown with private patio
10.0 out of 10, Exceptional, (20)
Bright Townhome: Walk to Johns Hopkins Bayview!
Bright Townhome: Walk to Johns Hopkins Bayview!
10.0 out of 10, Exceptional, (8)
Riverfront Country House on The Sassafras River
Riverfront Country House on The Sassafras River
10.0 out of 10, Exceptional, (12)
The price is $500
$603 total
includes taxes & fees
May 17 - May 18
Langford Creek Estate | Waterfront w/ HOT TUB + Deck!
Langford Creek Estate | Waterfront w/ HOT TUB + Deck!
10.0 out of 10, Exceptional, (3)
421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!
421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!
10.0 out of 10, Exceptional, (79)
Waterfront Home with Private Dock, Eastern shore, Betterton Chestertown MD.
Waterfront Home with Private Dock, Eastern shore, Betterton Chestertown MD.
9.8 out of 10, Exceptional, (80)
Relax on Kent Island in 3 Bedroom Home w/Waterview
Relax on Kent Island in 3 Bedroom Home w/Waterview
9.8 out of 10, Exceptional, (19)
The price is $156
$358 total
includes taxes & fees
May 27 - May 28
Historic Annapolis Home 1.5 blocks from center of town.
Historic Annapolis Home 1.5 blocks from center of town.
9.8 out of 10, Exceptional, (19)
Fantastic Spacious Eastport Home Easy Walk to Everything & Parking for 6 Cars!
Fantastic Spacious Eastport Home Easy Walk to Everything & Parking for 6 Cars!
9.6 out of 10, Exceptional, (98)
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Other property types in Chestertown
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
10.0 out of 10, Exceptional, (50)
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
10.0 out of 10, Exceptional, (3)
The price is $629
$1,417 total
includes taxes & fees
Jun 4 - Jun 5
The Heron's Nest at Atlantic Marina
The Heron's Nest at Atlantic Marina
10.0 out of 10, Exceptional, (264)
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Chestertown Vacation Homes information
Number of reviews | 570 |
---|---|
Accommodation | 367 Vacation Homes |
Lowest Price | $78 |
Highest Price | $629 |
Recent reviews of Chestertown hotelsExpedia verified reviews
5/5 Excellent
"Always clean "
A verified traveler stayed at Holiday Inn Express White Marsh, An IHG Hotel
Posted 2 days ago
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