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That South Point Joint - Assateague/Golf/Boat Ramp

Coastal South Point escape with peaceful Sinepuxent Bay views, bright sunlit spaces, & plenty of room to relax. This 3-bedroom, 2-bath home features a cozy gas fireplace, screened porch, private patio with BBQ, outdoor shower, fenced yard with fire pit, and a loft office/library. Enjoy easy access to Ocean City, Assateague State Park, and nearby golf, or simply unwind with sunrise views, wildlife watching, and breezy Eastern Shore charm. Ideal for beach days or quiet getaways. Stay and recharge.

Cozy behind the Yellow Doors

Welcome to “Cozy Behind the Yellow Doors!” This home is decorated with comfort and memorable quotes. It features 3 bedrooms and 2 bathrooms, a handicap ramp, and a backyard patio with a BBQ grill. Consider this house as your stay away from home in a quiet community located about 5 minutes from The Best Little Town known as Berlin Maryland, 15 minutes from Ocean City Maryland, about 10 minutes from Assateague State Park and the famous Frontier Town/ Water Park. Enjoy your vacation away from home!

Assateague surf cottage!

We welcome you to enjoy staying at our comfy, cozy surf cottage! This very clean cottage is just a stones throw away towards Assateague beaches, Ocean City, and “America’s coolest small town” Berlin, MD. This location provides plenty of activities such as mini golf, shopping, antiquing, restaurants, water parks, etc.. This newly renovated cottage has 3 bedrooms, 2 full baths, and a fully equipped kitchen. Our peaceful cottage also has a private pool, fire pit and quaint outdoor living space!

Assateague, Golf, Ocean City, all Within Minutes!

Worcester Co. Lic. #859 PLEASE NOTE: number of allowed guests: No more than 8 golfers. (Min age 25) No more than 10 adults. (Min age 25) Related families up to 12 guests. We do NOT rent to high school senior groups. Please note, we own the white house next to our STR. Occasionally you may see us there, however, we are committed to your comfort & privacy. Located 1.5 miles from Assateague Island beaches. 3 courses within .5 miles. Towels and linens for every guest.

"Jolly"- Houseboat Getaway

"Tiny house on the water"! Jolly is a 42ft Holiday Mansion. Baywater Landing buzzes with watermen & boaters by day & is a peaceful stargazing hotspot by night. She features a master suite & deck areas to enjoy! 35 mins from Ocean City & Assateague Island. 45 mins from Chincoteague Island. Jolly remains docked, but guests have access to kayaks and paddle boards at no additional charge. Baywater Landing is secluded- some even say "boring"- but we think that's the whole point!

White Marlin Cottage>HOT TUB<

Property Is Located Along RT 611 Within 3 miles to Ocean City Beach and 7 miles to Assategue Island Beach also within 3 miles of a Marina at the Bay to drop your boat in the water to enjoy fishing,crabing,swimming,skiing etc... White Marlin Cottage has a back yard patio with string lights , hot tub, grills, camp fire pit , a cast iron sink to clean your fish ,A sand box for children a yard where children can enjoy games and driveway space to park your boats etc...

Berlin/Ocean City Suite- Relax/Refresh near beach!

A remodeled, above garage guest suite separate from the main house in America's Coolest Small Town, Berlin,Md! You will benefit from a separate entrance to your above garage suite which will allow you to enjoy your own quiet space to relax and embrace the small, quaint town of Berlin, all while a mere 15 minutes to the beaches of OCEAN CITY and Assateague! Multiple dining experiences and tons of shopping await you in either historic Berlin or world famous Ocean City!

SpaciousCondo nearOcean City|Winery|Golf on 5Acres

Come stay in our 2nd Floor Condo on our private 5-Acre Property! Enjoy the Barn-Like look from the outside, but inside, find a modern & spacious condo with a fully-equipped kitchen. Located in Berlin, Maryland, you are minutes to Historic Berlin and only 15 minutes to all the fun that Ocean City, Maryland has to offer! Have your morning coffee on the deck and soak in the scenic views or pitch a tent, light up the fire pit, let the kids run wild! We'll see you soon!

Sweet Retreat

Sweet Retreat is conveniently located in Ocean Pines, Maryland. The premiere residential and resort community of Ocean Pines is located eight miles inland from the ocean resort town of Ocean City. Ocean Pines has over 9 miles of waterfront property and 3,000 acres of wooded areas. Community amenities include beaches, a yacht club, golf course, community center, a Beach Club Pool and other community pools. Passes are available at ocean Pines Association.

Secluded Waterfront - Beach 15mi, Kayaks, Firepit

Casa Blue Heron is a 2,254 ft² (209 m²) custom waterfront home with a private dock, firepit, and water views throughout - nestled on a tidal inlet connected to Chincoteague Bay - and near Assateague, Berlin, Ocean City, Snow Hill, and much more. ★ "A private and tranquil setting where it is impossible not to relax and appreciate nature… Wish I had booked an extra day!" Add us to your wish list by clicking the ❤️ in the upper-right corner.

Shire Retreat - Berlin, Assateague, Ocean City

Discover a haven of modern elegance at the Shire Retreat. Nestled just minutes away from Assateague Island with it's wild ponies, Berlin (the coolest small town in America), and vibrant Ocean City. This stylish retreat offers the perfect blend of tranquility and excitement. Perfect for gatherings or quiet relaxation. With its well-equipped kitchen and amenities. Your Maryland getaway awaits – where modernity meets coastal charm.

3 Bed 2 Bath House in the Heart of Berlin

Walking distance to downtown Berlin! This cute, cozy, cottage offers a large master bedroom with a king size bed and bath, and two guest bedrooms with one queen size bed, one full size bed, and a bathroom across the hall. Located in America’s Coolest Small Town featuring many shops, restaurants, and bars with a close by brewery. Ocean City beaches and Assateague Island National Seashore are about 10-15 minutes away.