Find Shopping Hotels in Chestertown, MD

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Our top choices for Chestertown hotels with shopping nearby

Property grounds
First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.6 out of 10, Exceptional, (108)
"Amazing and neat and very private "
United States
Alexander M.
The price is AED 364
AED 583 total
includes taxes & fees
24 Dec - 25 Dec
First Floor Studio Apartment in Historic Chestertown
Exterior
Candlewood Suites Aberdeen-Bel Air by IHG

Candlewood Suites Aberdeen-Bel Air by IHG

Candlewood Suites Aberdeen-Bel Air by IHG
2.5 star property
Bel Air
8.0 out of 10, Very Good, (470)
"Staff was super friendly, room was above expectations"
United States
Thomas
The price is AED 305
AED 341 total
includes taxes & fees
19 Dec - 20 Dec
Candlewood Suites Aberdeen-Bel Air by IHG
Premium bedding, in-room safe, desk, iron/ironing board
Residence Inn Aberdeen at Ripken Stadium

Residence Inn Aberdeen at Ripken Stadium

Residence Inn Aberdeen at Ripken Stadium
3.0 star property
Aberdeen
9.0 out of 10, Wonderful, (106)
"The stay was perfect everyone was super kind and helpful and I will definitely be back "
United States
Katlynn
The price is AED 371
AED 416 total
includes taxes & fees
11 Jan - 12 January 2026
Residence Inn Aberdeen at Ripken Stadium
Terrace/patio
Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina
3.0 star property
Grasonville
9.0 out of 10, Wonderful, (1001)
"We stayed overnight, coming to meet some people for a business meeting. Monica at the front desk provided great customer service and was extremely helpful in accommodating us. "
United States
Anthony
The price is AED 379
AED 421 total
includes taxes & fees
22 Dec - 23 Dec
Hilton Garden Inn Kent Island Marina
Exterior
Guest Suite for up to 2 in a Victorian on the Chester River

Guest Suite for up to 2 in a Victorian on the Chester River

Guest Suite for up to 2 in a Victorian on the Chester River
Millington
9.6 out of 10, Exceptional, (19)
"So pleased with all aspects of my stay. Clean, Comfortable, Quiet, Amenities all beyond expectation."
United States
Cynthia C.
The price is AED 250
AED 459 total
includes taxes & fees
15 Dec - 16 Dec
Guest Suite for up to 2 in a Victorian on the Chester River
Front of property - evening/night
The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club
4.0 star property
Stevensville
9.4 out of 10, Exceptional, (429)
"Beautiful hotel with friendly staff and great food! Comfortable bed, stayed at the Barn. "
United States
Rery
The price is AED 675
AED 843 total
includes taxes & fees
14 Dec - 15 Dec
The Inn at Chesapeake Bay Beach Club
Outdoor pool, a heated pool
Waterfront Oasis of Annapolis Star

Waterfront Oasis of Annapolis Star

Waterfront Oasis of Annapolis Star
Annapolis
10.0 out of 10, Exceptional, (81)
"Owners were great hosts. Loved this property!"
United States
Thomas
The price is AED 760
AED 1,520 total
includes taxes & fees
19 Dec - 20 Dec
Waterfront Oasis of Annapolis Star
Property grounds
Adorable two-bedroom retreat close to Easton, Denton, Centreville

Adorable two-bedroom retreat close to Easton, Denton, Centreville

Adorable two-bedroom retreat close to Easton, Denton, Centreville
Queen Anne
10.0 out of 10, Exceptional, (26)
"Quiet, quaint....perfect"
United States
Catherine M.
The price is AED 694
AED 1,316 total
includes taxes & fees
22 Dec - 23 Dec
Adorable two-bedroom retreat close to Easton, Denton, Centreville
Outdoor pool
Secluded Tiny Pool House -Private Pool -Self Check in

Secluded Tiny Pool House -Private Pool -Self Check in

Secluded Tiny Pool House -Private Pool -Self Check in
Glen Burnie
8.8 out of 10, Excellent, (9)
"Absolutely loved it, very quiet and peaceful, Jordan is an excellent host"
United States
Robert F.
The price is AED 400
AED 540 total
includes taxes & fees
14 Dec - 15 Dec
Secluded Tiny Pool House -Private Pool -Self Check in
Property grounds
Luxe Houseboat with Epic 360 Views of Baltimore Harbor

Luxe Houseboat with Epic 360 Views of Baltimore Harbor

Luxe Houseboat with Epic 360 Views of Baltimore Harbor
Baltimore
10.0 out of 10, Exceptional, (11)
"Everything was wonderful - the boat was just as described, even wit a few extra touches that meant a lot - snacks, water bottles, shampoo/conditioner, plenty of hangers, and the SUPER clean, just to name a few! We would love to stay again! Thank you so much!"
United States
Maggie P.
The price is AED 868
AED 1,972 total
includes taxes & fees
15 Dec - 16 Dec
Luxe Houseboat with Epic 360 Views of Baltimore Harbor
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.
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Top Chestertown Hotel Reviews

Hampton Inn Baltimore/Glen Burnie

Hampton Inn Baltimore/Glen Burnie

10/10 Excellent
"Rooms were clean and staff was very friendly "
Shailesh 1-night trip
Posted 3 days ago
Hampton Inn Baltimore/Glen Burnie

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