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Compare 421 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, 4 reviews
The price is $629
$1,438 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 review
The price is $209
$733 total
includes taxes & fees
Jun 3 - Jun 4
Suburban Retreat Near Baltimore Harbor
Suburban Retreat Near Baltimore Harbor
10.0 out of 10, Exceptional, 7 reviews
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Directly Across from Gate One & Steps from the Waterfront
Directly Across from Gate One & Steps from the Waterfront
10.0 out of 10, Exceptional, 180 reviews
Popular Historic Firehouse fully renovated with Parking and Pet Friendly
Popular Historic Firehouse fully renovated with Parking and Pet Friendly
10.0 out of 10, Exceptional, 51 reviews
Pet Friendly - Stone's throw from Annapolis City Dock with private back patio
Pet Friendly - Stone's throw from Annapolis City Dock with private back patio
9.8 out of 10, Exceptional, 7 reviews
Johns Hopkins Historic Renovated home - Location!
Johns Hopkins Historic Renovated home - Location!
10.0 out of 10, Exceptional, 2 reviews
The price is $143
$310 total
includes taxes & fees
Jun 3 - Jun 4
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 reviews
The price is $142
$339 total
includes taxes & fees
Jun 12 - Jun 13
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, 52 reviews
BAYSIDE BUNGALOW
BAYSIDE BUNGALOW
10.0 out of 10, Exceptional, 17 reviews
The price is $175
$272 total
includes taxes & fees
Jun 2 - Jun 3
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, 6 reviews
The price is $78
$121 total
includes taxes & fees
Jun 3 - Jun 4
Close to US Naval Academy, downtown Annapolis, Maryland Live Casino, BWI Airport
Close to US Naval Academy, downtown Annapolis, Maryland Live Casino, BWI Airport
10.0 out of 10, Exceptional, 7 reviews
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.
9.8 out of 10, Exceptional, 14 reviews
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, 81 reviews
Beautiful Luxury waterfront Property,clean,Fully sterilized,Family oriented.
Beautiful Luxury waterfront Property,clean,Fully sterilized,Family oriented.
9.6 out of 10, Exceptional, 18 reviews
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 reviews
History & Charm Near the Annapolis City Dock
History & Charm Near the Annapolis City Dock
10.0 out of 10, Exceptional, 7 reviews
Dog-Friendly Beach House with Kayaks, Marina & Dive Bar Weekend Access
Dog-Friendly Beach House with Kayaks, Marina & Dive Bar Weekend Access
10.0 out of 10, Exceptional, 10 reviews
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, 52 reviews
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, 4 reviews
The price is $629
$1,438 total
includes taxes & fees
Jun 4 - Jun 5
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
9.8 out of 10, Exceptional, 36 reviews
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 | 530 |
---|---|
Accommodation | 421 Vacation Homes |
Lowest Price | $78 |
Highest Price | $629 |
Recent reviews of Chestertown hotelsExpedia verified reviews
5/5 Excellent
"It’s was great "
A verified traveler stayed at La Quinta Inn & Suites by Wyndham Baltimore S. Glen Burnie
Posted 1 day ago
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