United States

5 Great Chesapeake Bay Resorts in VA

by Michael C. Upton  |  Published July 29, 2022

The first European settlers spotted the Chesapeake Bay in 1607 and ever since the water has called travelers from near and far to its beauty, recreation, and sustenance.

The Beach Club offers exclusive access (Photo: Courtesy of The Historic Cavalier Resort & Beach Club)

The Chesapeake Bay is a natural wonder and even a way of life for residents of the massive six-state watershed. It is a haven for sports enthusiasts, water recreationists, and those who border the 4,479 sq. mile body of water on the eastern shore of the United States. The Bay, as it is colloquially known, is the largest estuary in the United States and is separated from the Atlantic Ocean by the Delmarva (Delaware, Maryland, Virginia) Peninsula. Virginia claims the southernmost portion of the bay, from mainland to the Eastern Shore.

Virginia’s stretch of bay-front land is dotted with differing ways of life, from small, working-class towns to posh resorts offering exclusivity to travelers. Five Virginia resorts stand out for those looking to indulge in the finer things of life while enjoying a backdrop of sunrises, nature, and recreation.


On the banks of the James River sits Williamsburg, Virginia’s only AAA Four Diamond resort, Kingsmill. Kingsmill Resort offers three lodging options. Cottages on the James offer spectacular river views and enough room for a large family. Guest rooms and condos range from standard hotel-style rooms to three-bedroom deluxe accommodations. And the Estate at Kingsmill is a rental mansion. Whether visiting Historic Williamsburg, attending an event at William & Mary, or visiting nearby Newport News, Kingsmill is only a short drive. And Kingsmill attracts its own visitors, too, with three championship golf courses, a full-service spa, and four on-site eateries catering to many tastes.

Book at Booking.com

The Tides Inn is accessed by boat as much as car (Photo: Michael C. Upton for TravelMag)


Nestled in a quiet cove of the Rappahannock River for more than 75 years, The Tides Inn stands as a beacon of luxury on Virginia’s Northern Neck. Here the river soon meets The Bay. Oysters are plentiful and sunsets reflect off the still water. Guests who opt to skip a fireside view from the lawn can enjoy the sky and water from the Chesapeake Restaurant & Terrace, located on site. Visitors arrive by boat or car, with charging available for electric vehicles. A stay at The Tides is more than mere respite, as the resort offers cooking and craft classes, wine and whiskey pairings, and leisurely activities like golf and bike riding. The Tides’ emphasis on ecological sustainability makes it a coveted destination for all generations.

Book at Booking.com


Known as Cherrystone Family Camping Resort until it was rebranded Sun Outdoors Cape Charles in 2022, this resort is the only one of its kind on Virginia’s Eastern Shore. For those who enjoy the fun of a campground but insist on the amenities of a resort, Sun Outdoors fits the bill. Visitors can park their RV, rent a six-person cabin, or simply just pitch a tent in a premium site. The resort offers five swimming pools, an 18-hole mini golf course, and four fishing piers. Cape Charles is clam country, the most notable bivalve of the area being the Cherrystone. Aqua farms dot the waterways adding a delicacy to the menu of every nearby restaurant.

Book at Sunoutdoors.com

The Historic Cavalier is an architectural treasure (Photo: Courtesy of The Historic Cavalier Resort & Beach Club)


Although the Chesapeake Bay technically stops at Cape Henry, five miles south stands The Historic Cavalier Resort & Beach Club, which could not be left off this list. The Cavalier has hosted ten US presidents and luminaries from F. Scott Fitzgerald to Jimmy Buffett. Built in 1927, the location is crisp and modernized following a four-year, multi-million-dollar renovation. The Beach Club features a beachside swimming pool, cabanas, and an open-air bar, just a short golf cart ride from the hotel. Spirits aficionados love the hotel’s Hunt Room, which is home to Tarnished Truth Distilling Co. Samples of signature bourbon, rye, gin, and vodka are available in the tasting room.

Book at Booking.com


The Virginia Peninsula juts into The Bay surrounded by the York River, James River, and Hampton Roads channel. Here, historic Jamestown was founded in 1607 and today the area is home to Kiln Creek Golf Club & Resort. The inland retreat is known for its 6,972-yard, par 72 golf course designed by architect Tom Clark, but it is home to the newly renovated Lodge, which has begun to attract a new level of traveler. Casual meets haute cuisine at NEST Kitchen & Taphouse where seasonal menus offer refined versions of American classics and food built for a sharing atmosphere.

Book at Booking.com