Name: Graduate by Hilton Annapolis
Price range: AU$242

DoubleTree by Hilton Hotel Annapolis

210 Holiday Court Annapolis MD

AU$131

27 Sept - 28 Sept

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 ...

8.8/10 Excellent! (1,150 reviews)

"Rooms kept very clean and comfortable. Staff excellent, extremely friendly and helpful. Food very good and good portions."

Reviewed on 3 Sept 2026

Crowne Plaza Annapolis by IHG

173 Jennifer Rd Annapolis MD

AU$174

8 Sept - 9 Sept

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 ...

8.6/10 Excellent! (1,016 reviews)

"Clean room Helpful staff Great breakfast"

Reviewed on 3 Sept 2026

Graduate by Hilton Annapolis

126 West St Annapolis MD

AU$242

13 Sept - 14 Sept

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 ...

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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.

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

Annapolis MD

Stay at this holiday home in Annapolis. Enjoy a fitness centre, a garden and laundry facilities. Popular attractions Sandy Point State Park and Annapolis City ...

9.8/10 Exceptional! (53 reviews)

"Amazing place, friendly community, excellent crabbing."

Reviewed on 18 Aug 2026

Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna

Rock Hall MD

Stay at this family-friendly villa in Rock Hall. Enjoy free Wi-Fi, private pools and a fitness centre. Popular attractions Rock Hall Harbor and The Mainstay ...

10/10 Exceptional! (48 reviews)

"This is a beautiful place! Spacious and very accommodating for large groups. We had 19 there and just tons of room. The grandkids loved the pool. The back yard faces the bay and provides a magnificant view for sunsets. Moreover, we were on the patio between the pool and breezeway when the feels like ..."

Reviewed on 8 Aug 2026

First Floor Studio Apartment in Historic Chestertown

Chestertown MD

Stay at this golf apartment in Chestertown. Enjoy free Wi-Fi, private pools and a fitness centre. Popular attractions Wilmer Park and Sumner Hall are located ...

9.8/10 Exceptional! (125 reviews)

"Great place to stay."

Reviewed on 2 Sept 2026

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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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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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