Visit Chester
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! (92 reviews)
Great location for a relaxing, fun, family vacation
"Our family (ages 16 - 73) enjoyed our week here very much. Harry and Scott were great to work with and were always available to answer questions. We were aiming for a relaxing, low key week so we didn't stray too far from the house for adventures, but that just goes to show we had everything we needed ..."
Reviewed on Aug. 8, 2025
Historic Inns of Annapolis
58 State Circle, Annapolis, MD
The price is CA $140 per night from Aug 25 to Aug 26
CA $140
CA $207 total
Aug 25 - Aug 26
includes taxes & 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)
Great Location Near Naval Academy and Shops/Dining
"Wonderful historic hotel with clean rooms and friendly staff. Close to Naval Academy and waterfront shops and dining (5-minute walk, tops). Also close to Maryland State House (across the street) and several other historical sites. Loved our stay, with many future stays planned as we visit our new ..."
Reviewed on Aug. 11, 2025
Graduate by Hilton Annapolis
126 West St, Annapolis, MD
The price is CA $221 per night from Sep 2 to Sep 3
CA $221
CA $252 total
Sep 2 - Sep 3
includes taxes & 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 ...
9.2/10 Wonderful! (1,003 reviews)
"Beautiful hotel in a great location!"
Reviewed on Aug. 10, 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! (92 reviews)
Great location for a relaxing, fun, family vacation
"Our family (ages 16 - 73) enjoyed our week here very much. Harry and Scott were great to work with and were always available to answer questions. We were aiming for a relaxing, low key week so we didn't stray too far from the house for adventures, but that just goes to show we had everything we needed ..."
Reviewed on Aug. 8, 2025
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Annapolis
Stay at this vacation home in Annapolis. Enjoy a fitness center, a garden, and laundry facilities. Popular attractions Sandy Point State Park and Bay Hills Golf ...
10/10 Exceptional! (31 reviews)
"We had a great time overall! Pickleball courts and pool were the absolute highlights of the trip, with everyone getting in on the fun. The house was gorgeous with the sunroom being a bit hit every morning! Thanks!"
Reviewed on Jul. 20, 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
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.