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Check prices for these dates

In two weeks
22 May - 24 May
In two months
3 Jul - 5 Jul
In three months
31 Jul - 2 Aug
In four months
28 Aug - 30 Aug

Our top choices for Chestertown condo rentals

Property grounds

Luxe Row Home Steps to USNA Gate 3!

Luxe Row Home Steps to USNA Gate 3!
Historic District
10.0 out of 10, Exceptional, (3 reviews)
"Very recent remodel, and all top notch. You can tell the owners put their heart and soul into this property. All the rooms have been very nicely done. Bathrooms were beautifully done. Beds were comfortable. The area is very peaceful and quiet. We really enjoyed the back yard space also. Sat at patio table and used grill. Large TV’s everywhere! We were able to sit at patio table, grill some burgers and watch Final Four games from TV in kitchen area. If you have a Midshipman, this property is...
United States
Brian S.
The price is AED 738
AED 2,223 total
includes taxes & fees
11 May - 12 May
Luxe Row Home Steps to USNA Gate 3!
TV

Chapel Gate 3BR Steps to City Dock & Naval Academy

Chapel Gate 3BR Steps to City Dock & Naval Academy
Historic District
The price is AED 599
AED 1,724 total
includes taxes & fees
11 May - 12 May
Chapel Gate 3BR Steps to City Dock & Naval Academy
Dining

Historic Row Home in Downtown Annapolis

Historic Row Home in Downtown Annapolis
Historic District
The price is AED 801
AED 2,202 total
includes taxes & fees
10 May - 11 May
Historic Row Home in Downtown Annapolis
Interior

Luxury Baltimore Escape

Luxury Baltimore Escape
Canton
8.0 out of 10, Very Good, (1 review)
"The location was great so close to where we needed to be. Also very close to shops which was helpful. The kitchen was well appointed. The parking situation was a bit odd but we adjusted. Not sure where the third bedroom was located but luckily our guest did not need accommodations. "
United States
Jennifer R.
Luxury Baltimore Escape
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 Bayview Campus

Hampton Inn Baltimore Bayview Campus

6/10 Okay
"Breakfast was limited. Staff was friendly. Parking was plenty. Easy access to the city."
John 3-night trip
Posted 2 hours ago
Hampton Inn Baltimore Bayview Campus

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