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Compare 77 Apartments in Chester with updated reviews, rates, and availability.

Cozy place close to the city dock
Cozy place close to the city dock
9.8 out of 10, Exceptional, (68)

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

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)

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

Cozy 1st Floor King George one bedroom apartment right across from USNA
Cozy 1st Floor King George one bedroom apartment right across from USNA
10.0 out of 10, Exceptional, (29)

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

Guest quarters at the inn - 205
Guest quarters at the inn - 205
9.4 out of 10, Exceptional, (12)

Osprey's Landing at Atlantic Marinas - relaxing waterfront coastal retreat
Osprey's Landing at Atlantic Marinas - relaxing waterfront coastal retreat
9.8 out of 10, Exceptional, (45)
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

Waterfront Sunset Bayview: sleeps 6
Waterfront Sunset Bayview: sleeps 6
10.0 out of 10, Exceptional, (12)

Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!
Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!
10.0 out of 10, Exceptional, (118)

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)
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

Crowne Plaza Annapolis by IHG
5/5 Excellent
"Great and most comfortable bed!!!"
A verified traveler stayed at Crowne Plaza Annapolis by IHG
Posted 21 hours ago