TOP 30 Best Resort vacation rentals for families in Maryland

The Hyatt Regency Chesapeake Bay Golf Resort, Spa, and Marina is a luxurious lodging destination located in Cambridge, Maryland, United States. Situated on the picturesque U.S. 50, this institution offers a perfect blend of relaxation and recreation with its stunning waterfront views, championship golf course, rejuvenating spa treatments, and marina access. Guests can enjoy upscale accommodations, fine dining options, and a wide range of amenities to ensure a memorable stay. Whether you're looking to unwind in the spa, hit the links on the golf course, or explore the nearby attractions, the Hyatt Regency Chesapeake Bay Golf Resort, Spa, and Marina provides a truly unforgettable experience for all visitors.

Beach Baby Vacations is a premier real estate and travel agency located at 210 Worcester Street in Ocean City, Maryland, United States. Specializing in beachfront properties and vacation rentals, our experienced team is dedicated to helping clients find the perfect getaway for their next beach vacation. Whether you're looking for a cozy condo for a romantic weekend or a spacious beach house for a family reunion, Beach Baby Vacations has a wide selection of properties to choose from. Let us help you plan your dream beach vacation today!

Hyatt Regency Chesapeake Bay Resort is a luxurious waterfront retreat located at 100 Heron Point Rd in Cambridge, Maryland, United States. Nestled along the picturesque Choptank River, this resort offers stunning views and a serene atmosphere for guests to relax and unwind. The resort boasts elegant accommodations, top-notch amenities, and a variety of recreational activities including golf, spa treatments, water sports, and more. With multiple dining options serving delicious cuisine, a full-service marina, and beautiful outdoor spaces for events and weddings, Hyatt Regency Chesapeake Bay Resort is the perfect destination for a memorable getaway.

The Cook Travel Group - Dream Vacations is a premier travel agency located in Frederick, Maryland. We specialize in creating unforgettable dream vacations for our clients, offering personalized itineraries and top-notch customer service. Whether you're looking for a relaxing beach getaway, a thrilling adventure, or a luxurious cruise, our experienced travel experts are here to help you plan the perfect trip. Visit us at 5808 Winding Oaks Court and let us turn your travel dreams into reality.

Deep Creek Lake Vacation Rentals is a premier real estate and travel agency located at 45 Westward Way in McHenry, Maryland, United States. Specializing in providing top-notch vacation rental properties in the picturesque Deep Creek Lake area, our agency offers a wide range of accommodations to suit every traveler's needs. Whether you're looking for a cozy cabin for a romantic getaway or a spacious lakefront home for a family vacation, we have the perfect rental for you. Our friendly and knowledgeable staff are dedicated to helping you find the ideal vacation rental to make your stay at Deep Creek Lake truly unforgettable. Contact us today to start planning your dream vacation!

Cloud 10 Vacation Rental is a luxurious lodging option located at 141 Timber Ridge Road in McHenry, Maryland, United States. As a combination of a real estate agency and a travel agency, Cloud 10 offers guests the ultimate vacation experience. With stunning views and top-notch amenities, this institution provides a relaxing and comfortable stay for all visitors. Whether you're looking for a weekend getaway or a long-term rental, Cloud 10 Vacation Rental has everything you need for a perfect vacation.

Ski & Glee Vacation Rental is a premier lodging and real estate agency located in the picturesque town of McHenry, Maryland. Situated at 199 Sundance Way, this travel agency offers a wide range of vacation rental options for visitors looking to explore the nearby ski resorts and enjoy the beauty of Deep Creek Lake. Whether you're planning a winter ski trip or a summer getaway, Ski & Glee Vacation Rental has the perfect accommodations to suit your needs. With a focus on customer satisfaction and personalized service, this institution is dedicated to ensuring a memorable and enjoyable stay for all guests. Experience the charm and hospitality of McHenry with Ski & Glee Vacation Rental as your trusted accommodation provider.

Ocean City Resort Rentals LLC is a real estate and travel agency located on Coastal Highway in Ocean City, Maryland, United States. We offer a wide variety of vacation rental properties to ensure that you find the perfect home-away-from-home for your family getaway. Our dedicated staff is experienced in helping guests plan their beach vacation and are happy to provide information on local attractions and amenities. From fully equipped kitchens to linen and towel services, we strive to make your stay as comfortable and relaxing as possible. With our easy online booking process, you can quickly secure your rental and start planning your Ocean City adventure. Explore the endless activities, attractions, and scenery that Ocean City has to offer, from the famous Boardwalk to the beautiful beaches. Let Ocean City Resort Rentals help you create lasting memories on your next vacation.

Located in Thurmont, Maryland, the Ole Mink Farm Recreation Resort is a picturesque campground and lodging facility that has been providing unforgettable getaways for families and friends for over fifty years. With a variety of accommodations including luxury log cabins, camping cabins, and seasonal campsites, there is something for everyone to enjoy. Situated high atop the Catoctin Mountains, guests can explore scenic nature trails, fish in the pond or mountain stream, or simply relax by the campfire with some S’mores. The resort offers a range of amenities including a swimming pool, game room, playground, and planned weekend activities. Whether you are seeking a quiet retreat or a fun-filled family vacation, Ole Mink Farm is the perfect destination to create lasting memories.

Deep Creek Ski and Snowboard Rentals is a premier winter sports equipment rental shop located at 2778 Deep Creek Drive in McHenry, Maryland, United States. We offer a wide range of high-quality ski and snowboard gear for all skill levels, from beginners to advanced riders. Our knowledgeable staff is dedicated to providing top-notch customer service and helping you find the perfect equipment for your next snowy adventure. Whether you're hitting the slopes at nearby Wisp Resort or exploring the beautiful backcountry trails, Deep Creek Ski and Snowboard Rentals has everything you need to make the most of your winter vacation. Visit us today and gear up for an unforgettable experience on the mountain.

Ocvacations / Resort Rentals is a premier real estate and travel agency located at 3409 Coastal Highway in Ocean City, Maryland, United States. We specialize in providing luxurious vacation rentals and resort accommodations for visitors looking to experience the beauty of Ocean City. Our team of experienced professionals is dedicated to helping you find the perfect rental property for your getaway, whether you're looking for a cozy beachfront condo or a spacious family-friendly villa. With our extensive selection of properties and personalized service, Ocvacations / Resort Rentals is your go-to destination for a memorable and relaxing vacation in Ocean City.

Storch Deep Creek Lake Cabin Rentals is a premier lodging option located in Oakland, Maryland, United States. Situated at 231 Santa Fe Trail, this institution offers a variety of cozy and well-appointed cabins for rent, perfect for a relaxing getaway in the picturesque Deep Creek Lake area. As a real estate agency, Storch Deep Creek Lake Cabin Rentals also provides opportunities for those interested in purchasing a cabin of their own in this beautiful region. Additionally, their services as a travel agency can assist visitors in planning the perfect vacation experience, whether it be a family retreat, romantic escape, or outdoor adventure. With a focus on customer satisfaction and personalized service, Storch Deep Creek Lake Cabin Rentals is the ideal choice for a memorable stay in the heart of nature.

Castaways RV Resort LLC is a premier campground and lodging destination located at 12612 Eagles Nest Road in Berlin, Maryland, United States. Situated in a picturesque park setting, this resort offers a wide range of amenities and activities for guests to enjoy. Whether you're looking to relax by the pool, explore the nearby beaches, or participate in organized events and entertainment, Castaways RV Resort LLC has something for everyone. With spacious RV sites, cozy cabins, and modern amenities, this resort is the perfect place for a family vacation or weekend getaway. Come experience the beauty and tranquility of Castaways RV Resort LLC.

Lake Somerset Family Campground is a picturesque retreat nestled in the heart of nature at 8650 Lake Somerset Road, Westover, Maryland. This family-friendly campground offers a range of amenities and activities for all ages to enjoy. From spacious campsites to cozy lodging options, guests can choose the perfect accommodation for their stay. The park features stunning views of Lake Somerset, where guests can swim, fish, or simply relax on the shore. With hiking trails, playgrounds, and picnic areas, there is no shortage of ways to enjoy the great outdoors. Whether you're looking for a weekend getaway or a longer vacation, Lake Somerset Family Campground is the ideal destination for creating lasting memories with your loved ones.

Sandy Hill Family Camp is a picturesque campground and lodging facility located at 5752 Sandy Hill Road in Quantico, Maryland, United States. Nestled in a beautiful park-like setting, this family-friendly institution offers a peaceful retreat for visitors looking to escape the hustle and bustle of city life. With spacious campsites, cozy cabins, and modern amenities, Sandy Hill Family Camp provides the perfect opportunity for families to reconnect with nature and each other. Whether you're looking to relax by the campfire, explore hiking trails, or enjoy water activities on the nearby river, this institution offers something for everyone. Come experience the tranquility and beauty of Sandy Hill Family Camp for yourself.

Coldwell Banker Vacations - Vacation Rentals is a real estate and travel agency located at 6405 Coastal Highway in Ocean City, Maryland, United States. Specializing in Ocean City beach house rentals, they offer the best access to the sparkling boardwalk, sugar-white sands, and endless excitement of the Atlantic Ocean shoreline. With a variety of pet-friendly rental homes available, you can bring your furry friend along to enjoy the fun. With over 2344 vacation rentals offering internet access, you can stay connected throughout your trip. The professional housekeepers on their local Ocean City team ensure that all homes are clean and stocked with amenities for your arrival, allowing you to relax and enjoy your stay.

Taylors Island Family Campgrounds is a picturesque retreat located at 4362 Bay Shore Road in Taylors Island, Maryland. This charming campground offers a peaceful and scenic environment for families to relax and enjoy the great outdoors. With spacious lodging options and a variety of amenities, including picnic areas, playgrounds, and hiking trails, guests can experience the beauty of nature while creating lasting memories with their loved ones. Whether you're looking to pitch a tent, park your RV, or rent a cabin, Taylors Island Family Campgrounds provides a comfortable and welcoming setting for a fun-filled getaway.

The Princess Royale Oceanfront Resort is a luxurious lodging option located on the beautiful Coastal Highway in Ocean City, Maryland, United States. With stunning views of the ocean, this resort offers a truly relaxing and indulgent experience for guests. The resort features spacious and elegant rooms, top-notch amenities, and exceptional service. Guests can enjoy on-site dining options, a fitness center, indoor and outdoor pools, and direct access to the beach. Whether you are looking for a romantic getaway, a family vacation, or a business trip, the Princess Royale Oceanfront Resort is the perfect choice for a memorable stay.

Yogi Bear's Jellystone Park Camp-Resort in Williamsport, MD is a premier family-friendly destination located at 9550 Jellystone Park Way. This picturesque campground offers a variety of lodging options, including cabins, RV sites, and tent camping, surrounded by beautiful nature and plenty of amenities. Guests can enjoy activities such as swimming, hiking, fishing, and mini-golf, as well as daily visits from Yogi Bear and his friends. Perfect for a weekend getaway or extended vacation, this park is the ideal spot for outdoor enthusiasts and families looking to create lasting memories.

Kent Island Resort is a charming lodging facility nestled in the picturesque town of Stevensville, Maryland. Situated at 500 Kent Manor Drive, this resort offers a tranquil and relaxing retreat for guests looking to escape the hustle and bustle of city life. With its serene surroundings and luxurious accommodations, Kent Island Resort provides the perfect setting for a rejuvenating getaway. Whether you're seeking a romantic weekend escape or a peaceful family vacation, this resort caters to all travelers looking for a comfortable and welcoming place to stay. Experience the beauty of Kent Island and enjoy top-notch amenities and hospitality at Kent Island Resort.

Rocky Gap Casino, Resort & Golf is a premier destination located in Flintstone, Maryland, United States. This institution offers a luxurious casino experience, top-notch lodging accommodations, and an impressive golf course for guests to enjoy. Situated at 16701 Lakeview Road Northeast, Rocky Gap is the perfect getaway for those seeking relaxation and entertainment. Whether you're looking to try your luck at the casino, unwind in a comfortable room, or tee off on the stunning golf course, Rocky Gap has something for everyone. Come and experience the ultimate in luxury and leisure at Rocky Gap Casino, Resort & Golf.

Marigot Beach Condo Rentals is a premier real estate and travel agency located at 10100 Coastal Highway in Ocean City, Maryland, United States. We offer luxurious condo rentals with stunning views of the beach and ocean. Our properties are fully equipped with modern amenities and are perfect for a relaxing vacation or getaway. Whether you're looking for a weekend retreat or an extended stay, Marigot Beach Condo Rentals has the perfect accommodation for you. Contact us today to book your dream beach vacation!

Taylor-Made Deep Creek Vacations is a premier real estate and travel agency located in McHenry, Maryland, United States. Situated at 35 Towne Centre Way, this institution specializes in providing personalized vacation experiences at Deep Creek Lake. Whether you are looking for a cozy cabin retreat or a luxurious lakefront property, Taylor-Made Deep Creek Vacations has a wide range of accommodations to suit every need. With exceptional customer service and a dedicated team of professionals, this agency is committed to creating unforgettable memories for every guest. Book your dream vacation with Taylor-Made Deep Creek Vacations today!

CampMD Vacation Cottages is a family-oriented beach campground located at 15914 Camp Merryelande Road in Piney Point, Maryland, United States. Established in 1984, our waterfront cottages on St. George Island offer a unique and memorable vacation experience for guests of all ages. Each cottage is either beachfront or boasts stunning views of the beach and river, providing a peaceful and picturesque setting for your stay. Our cottages are individually designed and equipped with modern amenities such as free wifi, Cable TV, full kitchens or kitchenettes, and bathrooms. Whether you're seeking a cozy retreat for a quick getaway or planning a celebration with friends and family, we have accommodations to suit your needs. Our larger cottages can accommodate up to 24 guests, perfect for group gatherings and special occasions.

The Gaylord National Resort & Convention Center is a luxurious lodging destination located at 201 Waterfront Street in Fort Washington, Maryland. This stunning resort offers a wide range of amenities and services for guests to enjoy, including spacious rooms and suites, multiple dining options, a full-service spa, indoor and outdoor pools, and a state-of-the-art fitness center. The resort is also home to a world-class convention center, making it the perfect location for business meetings, conferences, and events of all sizes. With its prime waterfront location and convenient access to Washington D.C., the Gaylord National Resort & Convention Center is the ideal destination for both leisure and business travelers.

Southwinds Vacation Rentals is a real estate and travel agency located at 6 89th Street in Ocean City, Maryland, United States. The institution offers a luxurious oceanblock 5 bedroom townhouse with ocean view, parking for 4 vehicles, and accommodations for up to 12 guests. Guests can also take advantage of the free EV car charger and linen package during their stay. Southwinds A, located next door, also sleeps 12 and is perfect for large families looking to book both townhouses. Both properties have been featured in the Ocean City Sand Castle Tour and Metropolitan Magazine. Families can enjoy a video tour of the homes and hear from the designer.

Oceans Edge Vacations is a premier real estate and travel agency located at 15 51st Street in beautiful Ocean City, Maryland. We specialize in providing luxurious vacation rentals with stunning ocean views and top-notch amenities. Our dedicated team of professionals is committed to helping you find the perfect getaway for your next beach vacation. Whether you're looking for a cozy condo for a romantic retreat or a spacious beach house for a family reunion, we have a wide selection of properties to choose from. Let Oceans Edge Vacations help you make unforgettable memories by the sea.

Welcome to Ship's Cove Inn and Resort, a luxurious lodging destination located on the picturesque Yacht Club Road in Saint Michaels, Maryland. Our resort offers a peaceful retreat surrounded by stunning waterfront views and serene natural beauty. At Ship's Cove Inn and Resort, guests can enjoy comfortable accommodations, top-notch amenities, and personalized service. Whether you're looking for a relaxing weekend getaway or a romantic escape, our resort has everything you need to unwind and recharge.

Chesapeake Paradise Vacation Homes is a premier real estate and travel agency located at 1085 Rodgers Road in Deale, Maryland, United States. We specialize in providing luxurious vacation rental homes in the picturesque Chesapeake Bay area. Our properties offer stunning waterfront views, top-notch amenities, and easy access to outdoor activities like boating, fishing, and kayaking. Whether you're looking for a romantic getaway, a family vacation, or a corporate retreat, our team of experienced agents will help you find the perfect home for your needs. Book your dream vacation with Chesapeake Paradise Vacation Homes today and experience the beauty of the Chesapeake Bay like never before.

Experience the charm and beauty of St Michaels, Maryland with a historic vacation at this stunning property on Green Street. This real estate and travel agency offers a unique opportunity to stay in a beautifully preserved historic home in one of America's most picturesque towns. Immerse yourself in the rich history and culture of the area, while enjoying modern amenities and luxurious accommodations. Whether you're looking for a romantic getaway or a family vacation, A Historic St Michaels Vacation is the perfect destination for your next trip. Book your stay today and create memories that will last a lifetime.