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Compare 12 Condo Rentals in Chester with updated reviews, rates, and availability.
Annapolis Condominium in the heart of the historic center
Annapolis Condominium in the heart of the historic center
9.8 out of 10, Exceptional, (265)
Eastport Condo in Building with Rooftop Water Views of Spa Creek!
Eastport Condo in Building with Rooftop Water Views of Spa Creek!
10.0 out of 10, Exceptional, (9)
Waterfront 2-Bedroom Condo on Spa Creek
Waterfront 2-Bedroom Condo on Spa Creek
10.0 out of 10, Exceptional, (5)
Downtown Annapolis Condo w/ Free Parking + Coffee
Downtown Annapolis Condo w/ Free Parking + Coffee
10.0 out of 10, Exceptional, (16)
Walk to Main Street from Waterfront Condo w Pool and Parking
Walk to Main Street from Waterfront Condo w Pool and Parking
10.0 out of 10, Exceptional, (14)
Beautiful Condo - Water View Near City Dock
Beautiful Condo - Water View Near City Dock
9.6 out of 10, Exceptional, (137)
Chic Condo w/ Balcony in the Heart of Annapolis!
Chic Condo w/ Balcony in the Heart of Annapolis!
9.8 out of 10, Exceptional, (49)
Kent Island Waterfront Cottage
Kent Island Waterfront Cottage
9.2 out of 10, Wonderful, (7)
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 Chester
Kent Island Time - Enjoy Kent Island Waterfront-Pet Friendly!
Kent Island Time - Enjoy Kent Island Waterfront-Pet Friendly!
10.0 out of 10, Exceptional, (8)
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, (202)
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
10.0 out of 10, Exceptional, (20)
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 Chester hotels
Recent reviews of Chester hotels
5/5 Excellent
"Staff was friendly, suites were perfect and affordable, hot tub was nice, love how the lobby offers fresh cookies and coffee all day, it makes the entry area smell nice!"
A verified traveler stayed at Country Inn & Suites by Radisson, Annapolis, MD
Posted 1 day ago