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Compare 11 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, (269)
Beautiful Condo - Water View Near City Dock
Beautiful Condo - Water View Near City Dock
9.6 out of 10, Exceptional, (139)
Chic Condo w/ Balcony in the Heart of Annapolis!
Chic Condo w/ Balcony in the Heart of Annapolis!
9.8 out of 10, Exceptional, (52)
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)
Water-view condo with rooftop pool & balcony - minutes from downtown
Water-view condo with rooftop pool & balcony - minutes from downtown
9.2 out of 10, Wonderful, (9)
Unbelievable beach views for 6
Unbelievable beach views for 6
10.0 out of 10, Exceptional, (4)
Available for CW 2025 Walk to Main Street from spacious waterfront Condo w Pool and Parking
Available for CW 2025 Walk to Main Street from spacious waterfront Condo w Pool and Parking
10.0 out of 10, Exceptional, (14)
Kent Island Waterfront Cottage
Kent Island Waterfront Cottage
9.4 out of 10, Exceptional, (8)
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
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
9.8 out of 10, Exceptional, (38)
Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.
Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.
10.0 out of 10, Exceptional, (51)
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, (206)
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
Comfortable historic hotel
"The room was spacious and the lights and heater were on, so it was very inviting when we walked in. The bed was comfortable. The hotel itself has the historic feel we enjoy when we stay in Annapolis. The front desk clerk and valet drivers were all gracious and professional. My husband and I had an excellent stay for our weekend getaway."
A verified traveler stayed at Historic Inns of Annapolis
Posted 3 days ago