The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club sits on Kent Island across the Chesapeake Bay Bridge from Annapolis, so it is a nearby town rather than a downtown base, and it makes the list for travelers who want a Bay resort stay with a beach. Expect a relaxed atmosphere, water views and a holiday feel that contrasts with the brick streets of Annapolis.

The property has a beach on the Bay, an outdoor pool in season, a restaurant and bar and a range of room styles, from standard rooms to cottages and suites. Because it is a resort, much of the experience is on site: sunsets over the water, a drink on the deck and a walk on the sand. Facilities and rooms vary by season, so check availability and what is open when you plan your stay.

The drive to Annapolis crosses the Bay Bridge and takes roughly half an hour outside heavy traffic, though summer weekend congestion on the bridge can add a lot of time. Plan for that if you intend to spend full days in Annapolis. Many guests do the opposite: base here for beach time and take one or two day trips into the capital.

The location also suits visitors heading for St. Michaels and the Eastern Shore. Kent Island has casual seafood restaurants, marinas and a quieter pace, and the area is good for kayaking and fishing. Rates are highest in summer and fall quickly after the season, when the inn is peaceful.

Plan the stay around the Bay. Spend a morning on the beach or kayaking, take lunch at a casual seafood place on Kent Island and then drive to Annapolis in the afternoon for a cruise or an evening on City Dock. Alternatively, cross the other way to St. Michaels for a day on the Eastern Shore. The bridge crossing is part of the scenery, and the views from the span are memorable on a clear day. Check traffic reports on summer Fridays and Sundays, when delays can be considerable.

Seasonal tips matter here. Summer is the beach season, with warm water, long days and full restaurants, while spring and autumn are quieter and cooler, with good light for walks and photographs. Winter is peaceful and rates are lower, but some facilities close or reduce hours, so confirm what is open. Families should ask about cottage options with kitchens, and couples might request a room with Bay views. Whatever the season, bring layers, since the breeze off the water can be cool even on warm days, and plan your Annapolis days around the bridge traffic.

If you are traveling with a larger group or celebrating an event, ask about cottage and suite combinations, which can give everyone space while keeping the party together. The resort is also a popular choice for weddings and reunions, so check whether an event is scheduled during your stay, as it may affect quiet time on the beach. For a calm escape with the capital close at hand, the beach club is a relaxing alternative to the historic district.