Name: Crowne Plaza Annapolis by IHG
Price range: NZ$239
Rating: 8.8

DoubleTree by Hilton Hotel Annapolis

210 Holiday Court Annapolis MD

NZ$182

4 Oct - 5 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 ...

Historic Inns of Annapolis

58 State Circle Annapolis MD

NZ$276

18 Oct - 19 Oct

includes taxes & fees

Stay at this historic hotel in Annapolis. Enjoy free Wi-Fi, room service and a 24-hour fitness centre. Our guests praise the helpful staff and the clean rooms ...

9/10 Wonderful! (2,031 reviews)

"The property was not as advertised. The rooms were humid and had a slight musty smell. Several advertised amenities were missing from our rooms. One person in my group even found cigarette ashes on her comforter. I rented three rooms, and each one had an issue. I would not recommend this hotel."

Reviewed on 1 Oct 2026

Crowne Plaza Annapolis by IHG

173 Jennifer Rd Annapolis MD

NZ$239

26 Oct - 27 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 helpful staff and the clean ...

8.8/10 Excellent! (1,019 reviews)

"Pool was green and hot tub was empty. Our room's toilet seat was loose. And the first night there was no parking (we had to park in a bank parking lot) because they were hosting an event."

Reviewed on 29 Sept 2026

See all 1,205 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! (4 reviews)

"Overall property was great and as listed. Views onto the water was awesome, but getting in and out of the water would have been difficult if we wanted to, as we didn’t see a functioning ladder."

Reviewed on 20 Aug 2026

Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!

Chester MD

Stay at this family-friendly holiday home in Chester. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Northern Chesapeake Bay and Matapeake ...

10/10 Exceptional! (140 reviews)

"It’s a beautiful spot on the water and the house is so nicely laid out"

Reviewed on 28 Sept 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

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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