Holiday houses in Newport Bay

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.

Family · Location · Barbecue

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!

Location · Value · Condition

Water view at Ocean Pines Yacht Club Condo

Steps to 2 pools, 2 marinas, tiki bar and OP Yacht Club. Live music Thursday-Sunday evenings from 6-10pm, (in season). Beach day? Ocean City 15 min drive or walk to the marina and hop on a boat with friends and head across the bay into OC. Assateague Island is a 20 min drive. Crabbing? Fishing? Walk to one of the many Ocean Pines canals or ponds. Golfing? The links are just across the Parkway. Wedding party? Be footsteps away from make lasting memories. Free beach parking on 49th included

Location · Family · Parks

Home Away from Home , Pet friendly retreat

Welcome to Ocean Pines Getaway, Enter home through a beautiful covered porch with swing for two and lovely seating area. This sweet home has 3 bedrooms & 2 full baths. A fully stocked kitchen , with eat in breakfast nook, Also proper dining room plenty of seating for family Cozy living room with working fireplace. All season sunroom plenty of seating, pub table & bar. Doggie door in sunroom large enough for 100 lb dog, leads to fenced in backyard. $100 pet fee and $125 linens & bath towels.

Value · Location · View

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.

Family · Location · Layout

"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!

Value · Family · Breakfast

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...

Location · Family · Cleanliness

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!

Value · Family · Long stay

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!

Family · Value · Check-in

Bright and Airy Oceanside Condo

Wake up to stunning ocean sunrises from your private balcony and enjoy bay sunsets just outside your front door. This oceanside condo in midtown Ocean City, MD is steps from the beach!! Beachside with no street to cross. Park your car for free in our covered lot. Enjoy a walkable location near top restaurants, bars, nightlife, and attractions like Seacrets, Fager’s Island, Macky’s, breakfast at barn 34 and mini golf. Ideal for a convenient Ocean City beach vacation.

Location · Value · Air conditioning

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.

Value · Location · Indoor spaces

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.

Location · Value · Bathroom