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Find Adventure Hotels in Chestertown, MD

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Check availability on Chestertown Adventure Hotels

Top Chestertown Adventure Hotels

First Floor Studio Apartment in Historic Chestertown
Property grounds

First Floor Studio Apartment in Historic Chestertown

9.6 out of 10, Exceptional, (87)
"Quiet neighborhood and the best place to stay."
The price is SAR 372
SAR 596 total
includes taxes & fees
26 Jun - 27 Jun
First Floor Studio Apartment in Historic Chestertown
HGTV quality, private guest suite, country getaway with hot tub & fire pit
Terrace/patio

HGTV quality, private guest suite, country getaway with hot tub & fire pit

10.0 out of 10, Exceptional, (5)
"Was looking for an upscale beautiful place to stay for a family wedding. Found it! Tammy has tended to every detail at this VRBO. Gorgeous farmhouse chic. Very attentive to our texts. And always good to return to Centreville to see friends and family. "
The price is SAR 740
SAR 1,683 total
includes taxes & fees
23 Jun - 24 Jun
HGTV quality, private guest suite, country getaway with hot tub & fire pit
Waterfront Retreat with Private Dock and Beach
Property grounds

Waterfront Retreat with Private Dock and Beach

10.0 out of 10, Exceptional, (20)
"Everything about the place was great! Easy check in and super clean and homey feeling spot. Would recommend to anyone looking for a quiet and comfy place on the eastern shore. We will definitely be booking again if we come back to the area!"
The price is SAR 844
SAR 1,412 total
includes taxes & fees
16 Jul - 17 Jul
Waterfront Retreat with Private Dock and Beach
Waterfront Sunset Bayview: sleeps 6
Terrace/patio

Waterfront Sunset Bayview: sleeps 6

10.0 out of 10, Exceptional, (16)
"Loved the location, the property, and amenities. Would definitely stay again!"
The price is SAR 1,347
SAR 2,526 total
includes taxes & fees
26 Jun - 27 Jun
Waterfront Sunset Bayview: sleeps 6
Bayside Cottage steps from Rock Hall Harbor
Fridge, microwave, oven, stovetop

Bayside Cottage steps from Rock Hall Harbor

10.0 out of 10, Exceptional, (2)
"Property was nicely refurbished and furnished and well equipped. The younger set especially enjoyed the 5 bikes in good condition and the large yard to play sports. All in all, a great weekend stay!"
The price is SAR 758
SAR 1,456 total
includes taxes & fees
23 Jun - 24 Jun
Bayside Cottage steps from Rock Hall Harbor
Kent Island Resort
Aerial view

Kent Island Resort

3.5 star property
9.2 out of 10, Wonderful, (103)
"It's only 20 min from the downtown annapolis.Clean too."
The price is SAR 1,276
SAR 1,580 total
includes taxes & fees
30 Jun - 1 Jul
Kent Island Resort
Waterview Home by Kentmorr Marina, Beach Bar & Grill. Close to wedding venues.
Fridge, microwave, oven, stovetop

Waterview Home by Kentmorr Marina, Beach Bar & Grill. Close to wedding venues.

10.0 out of 10, Exceptional, (38)
"Easy check-in and access to the property. Clean and stocked with everything we needed. Great rental for families!"
The price is SAR 3,189
SAR 5,226 total
includes taxes & fees
22 Jun - 23 Jun
Waterview Home by Kentmorr Marina, Beach Bar & Grill. Close to wedding venues.
Waterview with Beach Volleyball! Walk to Marina & Kentmorr Beach Bar and Grill.
On the beach, sun loungers, beach towels

Waterview with Beach Volleyball! Walk to Marina & Kentmorr Beach Bar and Grill.

10.0 out of 10, Exceptional, (75)
"Property and Host were exceptional."
The price is SAR 3,189
SAR 5,158 total
includes taxes & fees
22 Jun - 23 Jun
Waterview with Beach Volleyball! Walk to Marina & Kentmorr Beach Bar and Grill.
Hampton Inn & Suites Edgewood/Aberdeen-South
Restaurant

Hampton Inn & Suites Edgewood/Aberdeen-South

2.5 star property
9.2 out of 10, Wonderful, (1000)
"Great stay!"
The price is SAR 348
SAR 389 total
includes taxes & fees
29 Jun - 30 Jun
Hampton Inn & Suites Edgewood/Aberdeen-South
Charming Pet-Friendly Stay - Near Bay & Beaches.
Fridge, microwave, oven, stovetop

Charming Pet-Friendly Stay - Near Bay & Beaches.

10.0 out of 10, Exceptional, (1)
"Tons of space with lots of amenities! Super nice neighbor hood and neighbors. Very clean as well!"
The price is SAR 670
SAR 1,838 total
includes taxes & fees
22 Jun - 23 Jun
Charming Pet-Friendly Stay - Near Bay & Beaches.
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.