Find Adventure Hotels in Chestertown, MD
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Our top choices for Chestertown adventure hotels
First Floor Studio Apartment in Historic Chestertown
First Floor Studio Apartment in Historic ChestertownChestertown
9.6 out of 10, Exceptional, (108)
"Amazing and neat and very private "
Alexander M.
The price is AED 364
AED 583 total
includes taxes & fees
16 Dec - 17 Dec
9.2 out of 10, Wonderful, (1000)
"Room was great staff friendly"
Melissa
The price is AED 300
AED 336 total
includes taxes & fees
21 Dec - 22 Dec
9.2 out of 10, Wonderful, (128)
"The property is very charming and the staff was extremely attentive and friendly. It's a beautiful area. Close to Annapolis and a lot of fun things to do."
Michael
The price is AED 527
AED 716 total
includes taxes & fees
14 Dec - 15 Dec
7.8 out of 10, Good, (1000)
"Our room is very clean, staff as always, are wonderful. Look forward to our stays."
jenny
The price is AED 350
AED 404 total
includes taxes & fees
21 Dec - 22 Dec
Secluded Tiny Pool House -Private Pool -Self Check in
Secluded Tiny Pool House -Private Pool -Self Check inGlen Burnie
8.8 out of 10, Excellent, (9)
"Absolutely loved it, very quiet and peaceful, Jordan is an excellent host"
Robert F.
The price is AED 400
AED 540 total
includes taxes & fees
14 Dec - 15 Dec
HGTV quality, private guest suite, country getaway with hot tub & fire pit
HGTV quality, private guest suite, country getaway with hot tub & fire pitCentreville
10.0 out of 10, Exceptional, (8)
"Such a great property. Second time coming and planning to come back next summer as well! Highly recommend! Amazing host!"
Renee P.
The price is AED 724
AED 1,612 total
includes taxes & fees
15 Dec - 16 Dec
Waterfront Retreat with Private Dock and Beach
Waterfront Retreat with Private Dock and BeachWorton
10.0 out of 10, Exceptional, (25)
"If you’re looking for a relaxing scenic getaway as a couple or a family …this retreat is it! The views from the dock were amazing and it was very peaceful. The kids loved playing on the sandy beach area by the dock! We also explored some beach areas nearby. The place was beautiful and perfect for our family of 4! The hosts were great and very helpful!"
Andrea M.
The price is AED 643
AED 1,144 total
includes taxes & fees
14 Dec - 15 Dec
Hidden Fells Point Gem / Private Courtyard Patio
Hidden Fells Point Gem / Private Courtyard PatioFells Point
9.6 out of 10, Exceptional, (92)
"Lenny & his housekeeper Elviea were exceptionally helpful, funny and a delight to be with! I spent two weeks here & it was the best place I've ever stayed compared to my stays in Korea, Ireland & several other US cities.
Highly recommend!"
Edward J.
The price is AED 202
AED 725 total
includes taxes & fees
14 Dec - 15 Dec
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.
Top Chestertown Hotel Reviews
Best Western Plus Hotel & Conference Center
10/10 Excellent
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