Vacation rentals in Whaleyville

Stunning private waterfront suite

Welcome to your cozy getaway with stunning water views from every room! This sweet 2-bedroom, 1-bath suite boasts a private entrance, a living room, and a cute kitchenette. Nestled in a peaceful, family-friendly neighborhood, you'll have year-round access to swimming pools, a golf course, tennis courts, a Yacht club, and lovely parks nearby. Only a quick 10-minute drive lands you on the sandy beaches and lively Boardwalk of Ocean City. Park in the driveway and step into your own private escape!

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.

Central Haven with Great Fenced Yard

You will be close to everything when you stay in this centrally-located home. The rear deck and grill are great for enjoying time outside. There's a fenced rear yard, making this home a perfect choice for man's best friend. We welcome dogs of any breed, size, and weight. We do offer size-specific pet amenities, so please share a photo of your dog when booking, or provide a basic description so we can set out appropriate amenities. For those traveling with cats, please inquire before booking.

Edgewater Escape - Luxury Bayfront Loft with Porch

You've never seen waterfront like this. Welcome to Edgewater Escape, a luxury bayfront loft apartment that hangs entirely over the bay on 7th street in downtown Ocean City. Sit on the bay front porch or hang out inside and watch boats, dolphin, birds, and sometimes even seals swim by within feet of the porch. The loft has a roomy king sized bed and the downstairs couch pulls out into a comfy queen bed. Recently renovated, it comes fully equipped for your big trip or quiet staycation :)

"Beebe Lynn" - Houseboat Getaway

A "Tiny house on the water". Your home-base for exploring Delmarva! Beebe Lynn is a vintage 32 ft Carver, nestled at Baywater Landing Marina in the stunning salt-water marshes of the Chincoteague Bay. From here, you are 35 minutes from Ocean City, MD, and 45 minutes from Chincoteague Island, VA. Beebe Lynn 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!

Salisbury Cottage

Relax in a quiet part of Salisbury in this cozy, 3 bedroom, 2 full bath home. A farmhouse feel welcomes you home after a long day at work, a sports trip, or vacation. Enjoy all new furniture including luxury bedding and smart TVs. Centrally located and close to downtown for shopping and dining at one of the many local restaurants. Only 30 minutes from the beaches of Ocean City & Assateague Island. One mile from Tidal Health PRMC and a half block away from Salisbury University.

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.

Tiny Cottage at Good Earth, near Bethany Beach

Welcome to the "Tiny Thyme Cottage" at Good Earth. The cottage is super cozy, perfect for a couple, with 1 queen bed, a kitchen & bathroom, and a small living area. You'll be staying on our 10-acre property, 4.7 miles from Bethany Beach. Convenient amenities include 2 on-site restaurants, market, theater, and ample parking. Our AIRBNB "Village" includes 2 tiny houses, a lofted apartment, and 2 cottages on the property. Staying at Good Earth is more than just a beach trip!

Hobbs & Rose | A Peaceful Cottage Escape

Built in 1941 from historic “clinker bricks,” this restored cottage is a dreamy place to slow down and reconnect. Surrounded by enchanted gardens and close to the beach, Hobbs & Rose is filled with charm—gorgeous living spaces, a carved marble soaking tub, and thoughtful details throughout. Enjoy a romantic getaway and unwind in our Sanctuary meditation room, where birdsong and forest friends welcome you. You relax—we’ve created every detail to help you feel restored.

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!

Steps to the Beach, Ocean View 1BR, Renovated

Steps to the beach! Fully renovated, bright, modern, clean condo with a balcony view of the ocean. Quiet North Ocean City location with walking distance to restaurants, bus, 7-11, Mini golf course, movie theater, parks, etc. Brand new appliances and furniture. Free WiFi, King Size Bed, 60" & 40" TVs. Pull Out Queen Sofa, Brand New Full Bathroom. Washer and Dryer in the unit. Keurig Coffee Station, iPhone Charging station. Private balcony. Free Parking Space.

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.