Best Chesapeake Bay Hotels

With waterfront views, a sailing school, and even a children’s program, the whole family will be happy here. But golfers, in particular, will delight in the Inn’s George W. Cobb-designed Golden Eagle Golf Course. There’s even a par-3 course for the family to enjoy. Seafood lovers will also be drawn to the Tides, as oysters and other local fare are mainstays on the menu.

As for the rooms and luxury suites, guests can expect soft and sumptuous linens accented by rich mahogany furniture, private patios overlooking lush gardens and Carter's Creek, and the option (depending on the type of room or suite) for pets, sleeper sofas, and in-suite wet bars.

• Sailing, tennis, and golf
• Exceptional seafood
• Spa and pool
• Bicycles on-site for guest use

The Inn at Perry Cabin offers a luxury bayside experience unlike any other. Take a morning sailing lesson and then relax on the expansive lawn’s Adirondack chairs before an afternoon of golf. Then enjoy a cocktail at on-site Purser’s Pub before an upscale dinner at the property’s STARS restaurant. And do it all in a beautiful, colonial-style estate that you just might recognize from its appearance in 2005 comedy smash Wedding Crashers. Of all the Chesapeake Bay hotels, this is surely the most iconic.

• Sailing, tennis, and golf
• Great on-site dining
• Spa and pool
• Fitness center
• Bicycles on-site for guest use

A safe bet at a reasonable price, the Hyatt Regency Chesapeake Bay Golf Resort, Spa & Marina is a premier AAA Four Diamond property. Its spa and waterfront setting set it apart, and the massive property gives visitors plenty to explore. Camp Hyatt (temporarily suspended as of April 2021) means the kids are taken care of, and onsite golf means you don’t even need to leave the property to hit the links—though the nearby city of Cambridge offers plenty of offsite activities.

• Marina and kayaks
• On-site restaurants
• Spa and pool
• Babysitting
• Golf course
• Game room
• Fitness center

Ethiopian-born, French-trained chef Meseret Crockett brings fresh ingredients and exceptional talent to her regularly updated menus at the inn’s restaurant, so you can rest assured that you’ll eat well. The grounds here are simply beautiful, and guests will notice that the meticulously tended gardens complement tastefully decorated rooms. You’ll also find a pool and even a private garden bath and shower (ahem, there's a clawfoot tub!)—perhaps the only amenity of its kind on Virginia’s eastern shore, or elsewhere, for that matter.

• Breakfast included
• Pool
• Bicycle on-site for guests use
• Private garden bath and shower

Located not too far from the Chesapeake Bay Bridge, the inn sits on Kent Island, one of the region’s iconic examples of Eastern Shore Maryland living. A beautiful waterfront setting just minutes from lively restaurants, bars, and shops means the Kent Manor Inn is peaceful while near the action, and the 19th-century building’s cozy rooms give the large property a boutique feel.

• Pool
• Firepit
• Kayaks and bicycles on-site for guest use

The Anchored Inn at Hidden Harbor offers new, clean accommodations on a smaller scale than major chain properties and at an affordable price. It is located near a handful of fun waterfront restaurants and even has its own small bar. If you’re looking for a place to base yourself while you spend your time on the water, the Anchored Inn at Hidden Harbour is a great option.

• Pool
• Paddleboards for guest use
• On-site dining

Thoughtful innkeepers and attention to detail make the Brampton Inn stand out as an excellent place to stay, and its proximity to Chestertown, Maryland, makes it even more appealing. Daily tea time provides guests with a pleasant treat, and a high-quality breakfast is also included with your visit. Most rooms and suites at the inn have working fireplaces and luxurious baths, making it an especially cozy choice in the winter for those looking for an offseason stay.

• Fireplaces
• Jetted bathtubs
• Firepit
• Breakfast and tea time included with room
• EV charging stations