8 Great Luxury Maryland Vacation Spots for Families

These waterfront Maryland resorts are perfect for multi-generational vacations and family getaways, 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, families in Maryland and the Washington, D.C. metro area often seek out properties within easy driving distance for multi-generational celebrations and weekend getaways. Here are eight leading luxury Maryland resorts that are excellent for families, as well as some “been there, done that” insights on activities and money-saving tips.

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 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 water view 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.

Insider Tips: Visit the Harriet Tubman Underground Railroad Visitor Center, explore the nearby Blackwater National Wildlife Refuge, and enjoy delicious donuts and pastries at Bay Country Bakery. Check the Special Offers page on the Hyatt Regency Chesapeake Bay’s website or use credit card loyalty points and programs for extra savings.

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 golden hour. The resort also features indoor and outdoor pools, tennis courts, a full-service spa and an 18-hole championship golf course.

Insider 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. Check the Inn at Perry Cabin’s website for money-saving deals and packages, especially during the off-season.

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.

Insider 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. If you’re planning a shoulder season visit, check the hotel’s website for special deals.

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.

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.

Insider Tips: Have breakfast or brunch at Iron Rooster, feast on jumbo lump crab cakes at The Boatyard Bar & Grill and take convenient water taxis to spots around the Annapolis Harbor. The hotel’s website provides information on money-saving deals and special perks from local companies.

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.

Insider 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 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 destination weddings and private events 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.

Insider 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.

Hilton Ocean City Oceanfront Suites

Ocean City, Maryland

Close-to-home beach destinations are popular for family vacations and multi-generational getaways, and Ocean City has always been a perennial favorite. The destination features 10 miles of sandy beaches, fun-filled attractions and an extensive array of dining options. The four-star Hilton Ocean City Oceanfront Suites is an excellent choice for families seeking spacious accommodations and extensive amenities in a prime beachfront location.

The Hilton Ocean City Oceanfront Suites offers dining venues, two outdoor pools overlooking the ocean, an indoor pool, a fitness center and a game room. Families can enjoy breathtaking sunrises and panoramic views of the Atlantic Ocean from the balcony of their oceanfront suite, and laundry rooms are available on every floor. The hotel is conveniently located just five blocks from Ocean City’s boardwalk and other nearby attractions.

Insider Tips: Treat your group to delicious ice cream at family-owned and operated Dumser’s Dairyland, savor fresh seafood at Ropewalk, and stroll along the boardwalk while snacking on tasty Thrasher’s Fries. Make sure to visit Assateague Island National Seashore and stop by Berlin’s Orange Blossom Bakery to buy some of their famous Apple Uglies along the way. Hilton Honors members can take advantage of special rates and benefits at this property.

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 taxi cruises 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.

Insider 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. Marriott Bonvoy loyalty program members can redeem points and earn added benefits at this resort.

Plan your next multigenerational vacation with expert advice from Destination Reunions. Sign up for the Destination Reunions newsletter today!

By Nancy Schretter, Contributing Editor

Header Photo: The Oaks Waterfront Hotel on Maryland’s Eastern Shore. (Photo credit: Nancy Schretter)