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Mad Men Beach House*DogFriendly*7 Min Walk 2 Sea*OUTDOOR MOVIE EXPERIENCE*Private Dock*WORK SPACE*New CRIB

After relaxing at the beach (just a 7 min walk away), unwind on our deck "watchin' the tide rollin' away!" Get the best of the bay & the beach with this dog-friendly hidden gem! Imagine evenings enjoying the bay breeze as you crack crabs on the deck! Relax inside our open-concept great room that allows everyone to be together. Fish on our private dock or use it for your own boat or jet-ski to dock there. Witness spectacular sunsets with our Kayaks. Enjoy a well lit, private work space to virtual work w/ high speed internet! A new wood CRIB now in master suite for restful sleep! The pools and tennis/pickleball courts are only a few blocks away for your enjoyment! Plus, a truly unique OUTDOOR MOVIE EXPERIENCE for all our guests to make for the best Vacay EVER!

The Oliver House

This property boasts breathtaking views of the Ocean City skyline and is nestled in a quiet neighborhood in West Ocean City. Bring your boat, paddle boards, kayaks and firewood for the most incredible vacation. Crabs and clams are plentiful and the kids can enjoy playing in the small beach area while splashing or swimming in the bay. Although you may never want to leave, it's a short drive to Ocean City's beaches and boardwalk, Assateague Island and the quaint must-see town of Berlin, Maryland.

3 BR Waterfront Home, Minutes to the Beach

Recently updated waterfront house located in the family-friendly Montego Bay community. Enjoy beautiful sunsets on the back deck or hop in one of the kayaks for a paddle around the wide-open canal. Try your hand at crabbing or fishing off the dock to catch your dinner. Within easy walking distance of the beach and Northside Park (about 10 minutes walk to both). Beach chairs, toys, boogie boards, and umbrellas are yours to use for fun in the sand and surf. The dock is available for boat tie-ups.

Salty Serenity

Relax and recharge at our cozy 3 bed/2 bath home in Ocean Pines, a peaceful community near Ocean City, MD. Enjoy bikes, kayaks, and a fire pit in the large backyard, or use the pools, marina, yacht club, and golf course in the neighborhood. Beach parking at the Ocean Pines Beach Club in Ocean City is included. You can explore the boardwalk, casino, outlets, and the many nearby restaurants. Or, visit Berlin, or see the wild horses at Assateague Island. Come experience all the area has to offer!

Private pool, waterfront, kayaks, bikes, firepits!

The Golden Quarter Farm is 150-acre waterfront, nature preserve, centrally located 5 miles from Assateague Island and its wild ponies, small town charm of Berlin, and OC Boardwalk. With a pool, kayaks, SUP, hiking trails, bikes, and birding, there's little reason to leave the property! Max of 8 adults. No parties. No Pets. Renters must sign a Rental Agreement & provide $250 refundable damage deposit. Pool open April-Sept 30th, NOT heated. 5% local room tax will be collected after booking.

Coastal Oasis in Ocean Pines

Coastal sanctuary is a private mother-in-law suite with a private entrance, just 15 minutes from Ocean City MD. 2 bedrooms, spa like bath, family room, w/sleeper sofa, kitchenette overlooking a marsh and bay. You will have the entire floor. 1000 sq feet. Daily visitors include deer, heron, birds and duck. Follow the deer path and use our stand-up paddle boards and/or Kayaks. Assateague wild ponies and Ocean City boardwalk are an close by. Berlin voted the coolest small town in America.

Stay Salty OC Beach House

Welcome to your ultimate getaway near Assateague State Park & Ocean City! Our spacious retreat sleeps 14 guests and boasts resort-style amenities including pools, a gym, kayaks, and tennis courts. Located just moments from beaches, charming towns, and exciting attractions, you'll have everything you need for an unforgettable vacation. With a fully stocked kitchen, game rooms, cozy reading nooks, puzzles, and a balcony, there's something for everyone. Book now and let the relaxation begin!

The Chesapeake House

Indulge in the ultimate beach getaway at The Chesapeake House, a newly remodeled 6-bedroom haven in Ocean City. Perfect for large families! Nestled on the serene canal, it offers aquatic adventures with kayaks and paddle boards. Enjoy evenings on the patio, grilling under bistro lights. Close to dining hotspots like Liquid Assets, Bull on the Beach, Lombardi's, and Kirby's. A mere stroll away from the beach, this retreat promises relaxation and recreation for your perfect coastal escape.

The Puskar’s Landing

Centralized to the beaches of Assateague Island. In the heart of Worcester County. Off the country roads of Maryland’s Eastern Shore. This cute rancher sits one mile from Chincoteague Bay with public boat ramps, a beach and pier. You can boat or drive approximately thirty minutes to Ocean City or Chincoteague Island for food and fun. This spacious property has plenty of green space for kids to run and play, enjoy the hot tub to unwind. Enough space to bring a boat or camper if needed.

"Jolly"- Houseboat Getaway

#BoatLife! Jolly is a 42ft Holiday Mansion. Baywater Landing offers a laid back, coastal style. It buzzes with watermen & boaters by day & is a peaceful stargazing hotspot by night. She features a master suite & 3 outside deck areas to enjoy! Just 35 minutes from Ocean City, Assateague Island, and Chincoteague Island, this is the epicenter of everything coastal! A firepit in the sand just outside your door round out everything you'll need for a stress-free vacation.

4 BR/3.5 Bath w/Community Pool, Hot Tub, Gym

Welcome to Bayside – your ultimate Eastern Shore getaway! Nestled in a prime location just minutes away from the renowned Assateague Island, the charming town of Berlin (often dubbed the coolest small town in America), the vibrant coastal energy of Ocean City, this place has it all. Whether you’re seeking a peaceful escape surrounded by nature or craving the lively attractions and activities nearby, Bayside has everything you need for an unforgettable vacation.

Waterfront Home & Golf Getaway

Discover the perfect blend of tranquility and adventure at this one-of-a-kind waterfront escape. Nestled in a peaceful country setting just minutes from the beach, enjoy morning coffee with birdsong or sunset cocktails by the bay. Paddleboard, kayak, or grab fresh crabs from Elliott’s Seafood and dine at the water’s edge. Bring your own boat or rent one locally—this serene, scenic retreat offers everything you need for the ultimate coastal getaway.