Chesapeake Bay Resorts for a Weekend Getaway

Getaway resorts

The best getaways are relaxing, fun, and carefree.  A trip to the shores of the Chesapeake Bay are perfect for some much needed getaway time.  The perfect accommodation makes any weekend escape that much more charming.  Grab a weekender bag and read our blog for the best large resorts where there are plenty of weekend options.

Hyatt Regency Chesapeake Bay Golf Resort, Spa and Marina, Cambridge, MD

If the waters of Eastern Maryland are calling your name, grab your friends and head for the peninsula’s all-inclusive Hyatt Regency Chesapeake Bay Resort, a waterfront resort on the Choptank River.  A stay on the 400 acre property includes views over a scenic private marina, world class golf course, and 3 pools, including an infinity pool.  The elite spa offers world class treatments, therapies, massages and an amazing thousand flower detox wrap.  Five outstanding restaurants and bars offer numerous cuisine choices from seafood to classic dishes.

The Inn at the Chesapeake Bay Beach Club, Kent Island, MD

Crossing the Chesapeake Bay Bridge you will see a 4 acre hotel surrounded by gardens, fountains, restaurants, and a barn.  The grounds are impeccably maintained and are a complement to the signature farm to table food.  If you are looking for something local, the Inn is located next to a local seafood shack and a water view restaurant.  The Inn and grounds have a wonderful rustic feel are harmonized by hardwood floors, marble fireplaces, and private balconies.  A perfect message at the spa makes this a memorable stay.

The Tides Inn, Irvington, VA

The Tides Inn is a waterfront resort just off the Rappahannock River near the Chesapeake Bay in Irvington, an hour from Hampton Roads  It is a full service boutique hotel with an award winning golf course, swimming pools, beach, and complementary paddleboards.  The 60 slip marina allows guests to be able to set sail with a Premier Sailing Instructor to explore the rich history of the Northern Neck. 

St. Michaels Harbour Inn, St. Michaels, MD

Dubbed the new “Hamptons” of the Chesapeake Bay, St. Michael’s is perfect summer enclave with the big yachts, longs driveways, and celebrities.  The St. Michael Harbour Inn invites guests to be in the heart of the boats, big and small, showcasing its mariner spirit.  One great perk is the complementary bicycles that allow guests to jaunt into the village experiencing a quaint main street.  At the end of a day, the Inn provides a tranquil setting, waterfront rooms, and complete relaxation.

Wylder Hotel, Tilghman Island, MD

Surround yourself with natural beauty, and escape to an island that seems worlds removed from anything happening back home. A part of the Chesapeake Bay famed Secret Islands; Tilghman Island offers pristine landscapes, crab, fishing, boating and complete relaxation.  A newly renovated Wylder Hotel sits on 9 acres of scenic Tilghman Island waterfront landscape.  The resort, which can only be reached by boat, offers outdoor decks, hammocks, an outdoor fireplace, a bocce court, lawn games, canoe, paddle-board, kayak and a saltwater pool. And of course, since this is Tilghman, there’s a 25 slip marina where you can bring your boat.  From the brand new décor to the restaurant, everything fits into its nautical theme.

The Inn at Herrington Harbour, North Beach, MD

This is a mariner’s delight with over 600 slips so you can get in a nautical state of mind.  With a beautiful private beach,  The Inn at Herrington Harbour is one of Chesapeake Bay’s west coast’s true gems.  The deconstructed layout of the resort allows guests to feel closer to the outdoors where there are plenty of landscaped paths, waterfalls, flower beds, and benches.   The individually placed rocking chairs by each guest room is a nice touch.   There’s plenty to fill the day with, such as, tennis, volleyball, cornhole, kayaks and paddleboards.  Ground floor guests rooms have patio with a hot tub to soak away the stress.

Kingsmill Resort, Williamsburg, VA

Located on a portion of the Kingmill Plantation, the Kingsmill Resort rests on  2,900 acres along the James River in Williamsburg, VA.  The 425 room full-service resort has a spa, 54 holes of golf, 15 clay-courts for tennis, outdoor paddle sports, and a full-service marina.  With all the river water sports available, guests can experience the lazy river ride, water slides and a zero-entry pool at the outdoor pool.  The award winning 54 hole golf courses, with a golf academy, have hosted 29 professional golf tournaments, including LPGA and PGA tour events.  When the day winds down, there are fire pits surrounding the pools for guests’ enjoyment and five restaurants to dine at.

The Inn at Perry Cabin

“Crab cakes and football – that’s what Maryland does” is the famous line from Wedding Crashers filmed at The Inn at Perry Cabin.  This Inn is as picturesque as it gets and has all the essentials for a weekend getaway – fireplaces, tubs, terraces, spa, views, and pool.  When you are done pampering yourself and want to enjoy the outdoors the Inn offers kayaking, bicycling, sailing a vintage yacht, or fishing.  St. Michael’s town is only a quick bike ride away and is filled with a trove of shops and sightseeing.  After an evening meal, you can cap the day off with a cocktail by the fireplace or garden to recount the blissful day.  Just remember you stayed where Hollywood stars stayed.

Chesapeake Beach Resort & Spa

The Calvert Cliffs are natures gem, a stunning sight that buffers right up to the Chesapeake Bay and on the doorstep of the Chesapeake Beach Resort and Spa.  You’ll visit to this resort for the picturesque views out over the bay, but you’ll stay for the three restaurants, full services spa, and balconies with a view.  Guests also enjoy bingo sessions and gaming which is open round the clock.