These waterfront Maryland resorts are perfect for multi-generational vacations and family escapes, offering exciting activities and attractions for all ages
Luxury resorts and hotels are popular options for family vacations and multi-generational trips. The best properties offer a combination of spacious rooms and suites, exceptional dining options, and a wide array of family-friendly activities and amenities. The key is to identify the ideal resort in a destination that appeals to the entire family.
While there are many kid-friendly luxury resorts located throughout the United States,multi-generational families in Maryland and the Washington, D.C. metro area often seek out properties within easy driving distance for long weekend getaways. Some of these are convenient options for families in the greater Mid-Atlantic region as well.
Here are seven leading luxury Maryland resorts that are excellent for multi-generational families, as well as some “been there, done that” insights on local activities and adventures.
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Hyatt Regency Chesapeake Bay Golf Resort, Spa, and Marina (Cambridge, Maryland)
Located just a short drive from major mid-Atlantic cities, the Hyatt Regency Chesapeake Bay Golf Resort is a top choice for multi-generational family vacations. Set on 342 acres along the Choptank River, this sprawling resort is packed with amenities for all ages and interests. Attractions include pools, restaurants, tennis courts, a championship golf course, a full-service spa, miniature golf, and fire pits perfect for making s’mores.
The Hyatt Regency Chesapeake Bay features a private beach, water sports, and a 150-slip marina that is bustling with boats during the summer months. The resort’s spacious waterfront rooms and massive indoor pool also make it appealing for off-season getaways. The spectacular sunsets are beautiful to watch here at any time of year.
Local Tips: Explore the nearby Blackwater National Wildlife Refuge, visit the Harriet Tubman Underground Railroad Visitor Center, and enjoy delicious donuts and pastries at Bay Country Bakery. Families can also go kayaking and boating with Black Water Adventures.
The Oaks Waterfront Hotel (Easton, Maryland)
Nestled in a peaceful cove on Maryland’s Eastern Shore, The Oaks Waterfront Hotel is a perfect destination for multi-generational celebration vacations or relaxing family getaways. The property offers a variety of luxurious rooms, suites, and cottages to suit the needs of every family group. Hotel buyouts for private events, family celebrations, and destination weddings are common on weekends during the spring, summer, and early fall.
Guests at The Oaks can enjoy a wide range of activities. Amenities include a saltwater swimming pool, complimentary bicycles and kayaks, fire pits, and free shuttles to nearby locations. Evening yacht cruises are also available on select days. The hotel’s outstanding restaurant, The Oak Room, serves dinner and provides a complimentary full breakfast for guests.
Local Tips: Take a ride on the Oxford-Bellevue Ferry, said to be the nation’s oldest privately operated ferry service, and don’t miss sampling the award-winning ice cream at the Scottish Highland Creamery. Make dinner reservations at The Oak Room well in advance to secure the best dining times and water views for your group.
Four Seasons Hotel Baltimore (Baltimore, Maryland)
Families and multi-generational groups enjoy spending time in Baltimore exploring the many attractions of Baltimore’s Inner Harbor. Some favorites include the National Aquarium, the Maryland Science Center, and the Port Discovery Children’s Museum. Maryland’s largest city is also a bustling cruise port and home to professional baseball games at Camden Yards.
The waterfront Four Seasons Hotel Baltimore is centrally located in Harbor East, within easy walking distance of Fells Point, Little Italy, and Inner Harbor attractions. The five-star luxury property features multiple restaurants, a family-friendly rooftop pool, a full-service spa, and lovely harbor views from most of its spacious guest rooms and suites. The hotel is known for its excellent service, and the concierge team can help families make vacation memories throughout their Baltimore getaway.
Local Tips: Visit Inner Harbor attractions early in the morning or later in the day to avoid the crowds and sample delicious pastries at Vaccaro’s Italian Pastry Shop. It’s also fun to get out on the water via a water taxi cruise or a colorful Chessie Dragon paddle boat.
The Inn at Perry Cabin (St. Michaels, Maryland)
The Inn at Perry Cabin has long been a premier destination for multi-generational celebrations and family vacations. Prominently featured in the Wedding Crashers movie, the Inn at Perry Cabin was recently voted the best mid-Atlantic resort by Travel + Leisure readers. The Inn’s luxurious rooms and suites, on-site dining, and gracious hospitality are exceptional.
Situated on Maryland’s Eastern Shore in historic St. Michaels, this waterfront gem offers an exciting array of amenities and fun-filled things for families to do. Boating, sailing, and watersports are a key part of the magic. Make sure to plan a small-group sailing excursion and go kayaking along the Miles River in the early morning, or during the late afternoon, or golden hour. The resort also features indoor and outdoor pools, tennis courts, a full-service spa, and an 18-hole championship golf course.
Local Tips: It’s fun to spend time exploring the town of St. Michaels. Visit the Chesapeake Bay Maritime Museum, go shopping on South Talbot Street, enjoy steamed crabs at The Crab Claw, and try a wide variety of premium ice cream flavors at Justine’s Ice Cream Parlour.
Suites at Silver Tree (Deep Creek Lake, Maryland)
Deep Creek Lake, located in Garrett County, Maryland, is a beautiful four-season destination filled with a wealth of outdoor activities. The 3,500 - acre lake is a popular spot for swimming, boating, and fishing. The area also features a ski resort, charming shops and restaurants, and multiple golf courses, plus farms and ranches.
The Suites at Silver Tree is ideal for families seeking a lakefront luxury hotel with resort-style amenities and magnificent water views. The two-building property offers four different styles of individually decorated suites, each with a gas fireplace and a kitchenette. Guests can enjoy a spacious lakefront area complete with a sandy beach, outdoor games, seasonal watersports, and exceptional on-site dining at the hotel’s restaurant, Dutch’s at Silver Tree. On-site boat rentals are also available at the property’s marina from late spring through early fall.
Local Tips: Head over to Alpaca Acres for tons of family fun, sample the ice cream at Lakeside Creamery, and indulge in custom-made treats at Deep Creek Donuts. Families will also enjoy visiting the Discovery Center at Deep Creek Lake State Park and taking a thrilling ride down the Wisp Resort Mountain Coaster.
Annapolis Waterfront Hotel (Annapolis, Maryland)
The Annapolis Waterfront Hotel occupies a prime harborfront location, placing families within easy walking distance of the best Maryland’s capital city has to offer. The Annapolis Waterfront Hotel has been recently remodeled with upgrades to its luxurious rooms, restaurants, and amenities. The property is part of Marriott’s Autograph Collection, allowing loyalty program members to redeem points and earn added benefits.
Multi-generational families can choose from a variety of spacious rooms and suites, many of which offer spectacular waterfront views of the harbor and Chesapeake Bay. Hotel amenities include two restaurants, a fitness center, and docking privileges for guests arriving by water. Scenic cruises aboard the property’s classic Schooner Woodwind sailing yachts are a popular way to get out on the water and explore the Chesapeake Bay.
Local Tips: Have breakfast or brunch at Iron Rooster, feast on jumbo lump crab cakes at The Boatyard Bar & Grill, and take a convenient water taxi to spots around the Annapolis Harbor. Tours of the U.S. Naval Academy are also available.
Gaylord National Resort & Convention Center (National Harbor, Maryland)
The Gaylord National Resort is an ideal destination for families seeking a fun-filled waterfront hotel with kid-friendly attractions and easy access to Washington, D.C. This luxury resort is beautifully situated on the banks of the Potomac River in Maryland’s National Harbor. Guests can take convenient water taxis to Washington, D.C., and Alexandria, Virginia, from the National Harbor dock.
One of the highlights of the Gaylord National Resort is its 19-story climate-controlled garden atrium, which provides a beautiful place to relax regardless of the weather. The hotel also features renovated rooms and suites, multiple restaurants, a full-service spa and fitness center, a large indoor pool, and a seasonal outdoor splash zone for kids. Gaylord National Resort is known for its outstanding family-focused programs and festivities, including superhero-themed packages and its ICE! Christmas season event.
Local Tips: National Harbor offers a wide variety of activities and attractions for families. Ride the Spirit Park Carousel and take a spin on The Capital Wheel at night to enjoy the colorful LED light display and gorgeous skyline views.
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