Name: Crowne Plaza Annapolis by IHG
Price range: AU$172
Rating: 8.8

Graduate by Hilton Annapolis

126 West St Annapolis MD

AU$241

26 Oct - 27 Oct

includes taxes & fees

Stay at this business-friendly hotel in Annapolis. Enjoy free Wi-Fi, breakfast (surcharge) and a 24-hour fitness centre. Our guests praise the bar and the helpful ...

DoubleTree by Hilton Hotel Annapolis

210 Holiday Court Annapolis MD

AU$182

21 Oct - 22 Oct

includes taxes & fees

Stay at this business-friendly hotel in Annapolis. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Our guests praise the restaurant and the helpful ...

Crowne Plaza Annapolis by IHG

173 Jennifer Rd Annapolis MD

AU$172

16 Nov - 17 Nov

includes taxes & fees

Stay at this business-friendly hotel in Annapolis. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Our guests praise the helpful staff and the clean ...

8.8/10 Excellent! (1,003 reviews)

"Elevators were often down to only one working. Very slow elevators long lines constantly. Restaraunt bar area has horrific service waited 30 minutes still never got service so had to leave and go next door. Front desk excuse is “hotel is old.” Imagine if Waldorf used that excuse."

Reviewed on 18 Oct 2026

See all 1,208 properties in Chester

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.

Crab Alley | Bayfront Hot Tub & Game Room

Chester MD

Stay at this holiday home in Chester. Enjoy free Wi-Fi, laundry facilities and a pool table. Popular attractions Bodkin Island and Chesapeake Bay Environmental ...

10/10 Exceptional! (5 reviews)

"What a wonderful weekend. This house was lovely, clean, and so convenient to dock our boat. Thank you for sharing your home. Blessings"

Reviewed on 4 Oct 2026

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Annapolis MD

Stay at this holiday home in Annapolis. Enjoy free Wi-Fi, breakfast (surcharge) and a garden. Popular attractions Annapolis City Dock and Bay Ridge Beach are ...

9.6/10 Exceptional! (19 reviews)

"We had a lovely stay at this charming cottage on the bay. Everything was well maintained, the host provided strong communication, the grounds are beautiful, and our family found the hot tub to be a wonderful place to both relax amidst nature and reconnect . Also our 2 little dogs felt very much at ..."

Reviewed on 3 Aug 2026

Cute, Cozy 2-bedroom house near Annapolis with water access

Crownsville MD

Stay at this holiday home in Crownsville. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Joyces Marina and B&A Trail are located ...

9.8/10 Exceptional! (28 reviews)

"Multiple stays throughout the summer and now into fall. Great property! Quiet, clean and very responsive host."

Reviewed on 16 Oct 2026

See all properties in Chester

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.

Stay near popular Chester attractions

Chesapeake Exploration Center

Learn about the events happening in Chesapeake Exploration Center during your trip to Kent Narrows. Stroll along the area's marina or simply enjoy its seafood restaurants.

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