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 8 Aug. 2025
Historic Inns of Annapolis
58 State Circle, Annapolis, MD
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! (1,836 reviews)
"There were no ghosts!"
Reviewed on 20 Aug. 2025
Graduate by Hilton Annapolis
126 West St, Annapolis, MD
The price is AU$285 per night from 2 Sept to 3 Sept
AU$285
2 Sept - 3 Sept
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! (1,009 reviews)
Cool place, comfy bed!!!
"Cool place, cool vibe! Loved all the pictures and the strong decor. Front desk check in and out was quick & efficient. The parking valets were quick and very friendly. Walking distance to shopping, restaurants and bars! The bed was super comfy! We would definitely stay here again!"
Reviewed on 20 Aug. 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 8 Aug. 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 20 Jul. 2025
Waterfront Oasis of Annapolis Star
Annapolis
Stay at this apartment in Annapolis. Enjoy free WiFi, private pools, and cable/satellite TV service. Popular attractions U.S. Naval Academy Golf Club and Maryland ...
10/10 Exceptional! (76 reviews)
"Great place. Well organized and really nice host."
Reviewed on 17 Aug. 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 in Chesapeake Exploration Center during your trip to Kent Narrows. Stroll along the area's marina or simply enjoy its seafood restaurants.