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Compare 85 Apartments in Chestertown with updated reviews, rates, and availability.

Bay View Studio Apartment
Bay View Studio Apartment
10.0 out of 10, Exceptional, (42)

Newly restored apartment in the heart of Chestertown
Newly restored apartment in the heart of Chestertown
9.8 out of 10, Exceptional, (20)

Historic Downtown Garden Oasis with Private Patio
Historic Downtown Garden Oasis with Private Patio
10.0 out of 10, Exceptional, (25)

Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace
Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace
The price is SAR 604
SAR 823 total
includes taxes & fees
31 Mar - 1 Apr

18th Cent. Charm in Historic Downtown Annapolis
18th Cent. Charm in Historic Downtown Annapolis
9.8 out of 10, Exceptional, (6)
The price is SAR 713
SAR 1,377 total
includes taxes & fees
13 Apr - 14 Apr

COZY DOWNTOWN APARTMENT-Naval Academy Vicinity
COZY DOWNTOWN APARTMENT-Naval Academy Vicinity
9.8 out of 10, Exceptional, (38)

Quiet SPA Loft Studio Apt. Relaxing Getaway with private garage Annapolis
Quiet SPA Loft Studio Apt. Relaxing Getaway with private garage Annapolis
9.6 out of 10, Exceptional, (29)

'At Fells Point' CitySide - 'Tons better than a hotel!'
'At Fells Point' CitySide - 'Tons better than a hotel!'
9.8 out of 10, Exceptional, (187)
The price is SAR 330
SAR 771 total
includes taxes & fees
1 Apr - 2 Apr
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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Other property types in Chestertown

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
10.0 out of 10, Exceptional, (209)

240' Private Beachfront @Kent Island Love Point - Great for Large Groups
240' Private Beachfront @Kent Island Love Point - Great for Large Groups
10.0 out of 10, Exceptional, (180)

Chesapeake Houseboat Getaway on Kent Island, Maryland
Chesapeake Houseboat Getaway on Kent Island, Maryland
9.8 out of 10, Exceptional, (22)
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.
Recent reviews of Chestertown hotels
Recent reviews of Chestertown hotels

Historic Inns of Annapolis
5/5 Excellent
"Love the convenience that we valet parked the car and didn’t need it again until we checked out. Felt totally safe as we walked around to first class shops and restaurants. The property was clean and comfortable.
We had an issue with the pillows on the bed. Too new and full. Called to the desk and had different pillows brought up and like Goldie locks, they were just right. Check in was in another building but that didn’t matter. Really enjoyed the historic ambiance. Would stay there again our next time in Annapolis. "
A verified traveler from MURRYSVILLE stayed at Historic Inns of Annapolis
Posted 2 days ago
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