Visit Chester
Historic Inns of Annapolis
58 State Circle, Annapolis, MD
$143 nightly
The price is $163 total per night from Aug 10 to Aug 11
$163 total
Aug 10 - Aug 11
Total includes taxes and fees
Book a stay at this historic hotel in Annapolis. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the helpful staff and the clean ...
8.8/10 Excellent! (1,832 reviews)
"Enjoyed the stay! Beautiful place!"
Reviewed on Jul 28, 2025
Graduate by Hilton Annapolis
126 West St, Annapolis, MD
$155 nightly
The price is $177 total per night from Aug 17 to Aug 18
$177 total
Aug 17 - Aug 18
Total includes taxes and fees
Stay at this 4-star business-friendly hotel in Annapolis. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the bar and ...
9.4/10 Exceptional! (1,009 reviews)
"Beautiful place, very clean room, but the best thing by far was the staff. Everyone we met was friendly and helpful. Thank you so much for a greay stay!!"
Reviewed on Jul 27, 2025
DoubleTree by Hilton Hotel Annapolis
210 Holiday Court, Annapolis, MD
$99 nightly
The price is $112 total per night from Aug 3 to Aug 4
$112 total
Aug 3 - Aug 4
Total includes taxes and fees
Stay at this 4-star business-friendly hotel in Annapolis. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the restaurant and the ...
8.4/10 Very Good! (1,018 reviews)
7 out of 10 stars
"The hotel is older and as we walked through we were saying how it could be (& you can tell it was) a really nice hotel. Don’t misunderstand, it was a nice hotel, but you can tell it’s ‘used’. There are scuffs on doors and walls, there are tiles broken on floors, etc. the room itself was clean. The ..."
Reviewed on Jul 27, 2025
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.
Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!
Chester
Book a stay at this family-friendly vacation home in Chester. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Matapeake State Park and ...
9.8/10 Exceptional! (91 reviews)
"This house was charming and comfortable. The view was spectacular. Neighbors and friendly. The whole place has a serene feel to it. In addition, the owners were very helpful and responsive. We will be back again!"
Reviewed on Jul 27, 2025
Floating 2 bed 2 bath condo stunning views of the bay
Stevensville
Stay at this houseboat in Stevensville. Enjoy a beach locale and an in-room coffeemaker. Popular attractions Matapeake State Park and Romancoke Wharf County ...
8/10 Very Good! (4 reviews)
"Beautiful view! Could hear the tiki bar music from the top. Easy to get to woth lots of things to do nearby."
Reviewed on Jun 7, 2025
The Heron's Nest at Atlantic Marina
Pasadena
Stay at this cottage in Pasadena. Enjoy free WiFi, a garden, and balconies or patios. Our guests praise the helpful staff in our reviews. Popular attractions ...
9.8/10 Exceptional! (298 reviews)
"Wonerful place! Cozy, comfortable and clean. Beautiful view from the windows and the porch where we started and ended our days."
Reviewed on Jul 27, 2025
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.
Popular places to visit
Chesapeake Exploration Center
Learn about the events happening at Chesapeake Exploration Center during your trip to Kent Narrows. Stroll along the area's marina or simply enjoy its seafood restaurants.
- Chesapeake Exploration Center
- U.S. Naval Academy
- Chesapeake Bay Bridge
- Sandy Point State Park
- Annapolis City Dock
- Navy-Marine Corps Memorial Stadium
- Anne Arundel Medical Center
- Westfield Annapolis Mall
- St. Michaels Winery
- Rock Hall Harbor
- Annapolis Harbor Center Shopping Center
- Annapolis Maritime Museum
- Maryland Quiet Waters Park
- Annapolis Mall Shopping Center
- Maryland State House
- Queenstown Premium Outlets
- Chesapeake Bay Maritime Museum
- Annapolis Harbour Center
- Queenstown Harbor Golf Club
- William Paca House
- Chesapeake Bay Environmental Center
- Annapolis Landing Marina
- Avalon Theatre
- Ego Alley
- Eastern Neck National Wildlife Refuge
- Queenstown Harbor Golf Links
- Rolphs Wharf Marina