Waterfront vacation rentals in Henlopen Acres

Find and book unique waterfront rentals on Airbnb

Top-rated waterfront rentals in Henlopen Acres

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Guest favorite

A pathway leads from the side of the house towards the water, with steps ascending to a deck area. The canal is visible in the background, bordered by other homes. The exterior features light-colored siding and a small landing at the base of the stairs.

Home in Ocean City

4.96 out of 5 average rating, 102 reviews

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.

Superhost

Townhouse in Ocean City

4.85 out of 5 average rating, 193 reviews

DownByTheBay 115- Waterfront/4BR/Sleep 15/Pool

On The Bay, Beautifully furnished 4BR/3.5BR located in the heart of Midtown Ocean city, MD. * 1 block to beach- 5 min walk * Bonfire Buffet, Dough Roller, Ice cream Parlor - 2 min walk * Mini golf - 2 min walk * Bowling - 5 min walk * OC Boardwalk -7 minute by car * Seacrets - 5 minute by car * Convention Center - 5 minute by car * bus stop -1min walk * Market64- 2min drive *This property DOES NOT provide linens/towels* **Please FIND us at Down by the Bay OCMD For current Promotion**

Guest favorite

A wooden dock extends along the calm water, flanked by manicured grass and several shrubs. The serene waterfront is framed by a clear blue sky, showcasing the peaceful connection between nature and the property.

Home in Millsboro

5 out of 5 average rating, 10 reviews

Bayfront Oasis Vacation Rental

Waterfront panoramic views with a crabbing dock and boat slip. 4 bedrooms (full/twin bunkbeds, 2 twin beds + full bath, queen bed + full bath, king bed + full bath, and sleeper sofa in living room); up to 14 guests. Additional features include ½ bath, sunroom, living room, kitchen, laundry room (washer/dryer), and gaming room. Outdoor space with dining table, outdoor kitchen, firepit, gazebo, cornhole. Resort amenities; swimming pool, bikes, playground, pickleball, dog park, marina, store.

Top guest favorite

A serene waterfront view is presented, showcasing a grassy area beside a canal. Colorful chairs are placed at the edge, and boats are visible along the dock. The scene includes residential homes lining the opposite side of the waterway, with clear skies overhead.

Home in Selbyville

4.98 out of 5 average rating, 40 reviews

Waterfront, Bring your own boat! Huge canal home.

Look no further for your vacation rental at the beach, this house has it all! Extraordinary waterfront coastal home with amazing views of the Assawoman Bay and the Ocean City skyline. With 2 expansive living areas with open floor plans, there is plenty of space for multiple parties to unwind. Relax on the deck or in the yard and enjoy the canal breezes. Cook in the updated kitchen and enjoy panoramic water views! Enjoy the beach in Fenwick Island, DE/Ocean City, MD just over 2 miles away.

Guest favorite

A serene view from the loft window captures a winding canal lined with waterfront homes. Boats are anchored along the docks, and lush greenery frames the scene, while soft evening light enhances the tranquil ambiance.

Home in Ocean Pines

4.91 out of 5 average rating, 167 reviews

Waterfront Beach Home in the Ocean City, MD Area

There is room for 8 adults (plus 2 kids). Located in the premiere seaside community in the Ocean City area, Ocean Pines, this wonderful waterfront home provides amazing views both day and night. The open floor plan provides guests with lots of room to socialize and bond, but also has secluded bedrooms that provides needed privacy. The outdoor living area is to die for. Sit back and watch the sun set over the canal while you catch up with friends or loved one. Use our bikes!

Superhost

A sandy area features several orange Adirondack chairs arranged around a fire pit, with two blue umbrellas providing shade. The marina and water are visible in the background, surrounded by lush greenery and trees.

Houseboat in Snow Hill

4.77 out of 5 average rating, 128 reviews

"Serendipity"- Houseboat Getaway

Serendipity is docked at an active marina with watermen and pleasure cruisers, nestled off the Chincoteague Bay. Sleeps up to 4 adults craving coastal tranquility. From the boat, the Chincoteague Bay is in view and ready to be explored. Enjoy a full spectrum of awe-inspiring coastal wetlands, historic downtown areas, and beaches all within a few minutes' drive. Truly, the perfect setting for a much deserved recharge. 35 Minutes from Ocean City, Assateague Is, and Chincoteague Is.

Superhost

A scenic view reveals a spacious waterfront lawn framed by trees, with a picnic table positioned on pebbled ground. A glimpse of the water can be seen in the background, highlighting the serene setting of the cottage.

Cottage in Lewes

4.75 out of 5 average rating, 20 reviews

Dock Holiday - Waterfront A-frame Cottage

Kick back and relax with family and friends in this comfy and stylish mid century modern waterfront cottage in Angola by the Bay, a gated community featuring community crab docks, trails, a pool, and tennis and pickleball. House has huge waterfront lawn for outdoor games. Minutes to the action and amenities nearby such as historic Lewes, Cape Henlopen State Park, Dewey Beach and the famous Rehoboth Beach boardwalk. Bring your own boat or kayaks and get out on the water!

Guest favorite

A serene view of the bay is captured through large glass doors, showcasing water under a soft, colorful sky at sunset. In the foreground, a decorative mug sits on a quartz kitchen countertop, inviting relaxation.

Condo in Dewey Beach

4.84 out of 5 average rating, 193 reviews

On the Bay, Private Beach-Boat Slip

Enjoy your own piece of paradise! Walk out the door 10 steps to the water! Modern condo located on the bay with great views, a patio, a grill, a private beach, boat slip, and 2 blocks to the ocean. Perfect for couples and small families! This is a well-appointed 500 sqft open concept condo with 1 bedroom, office & 1 bath. We take great pride in our condo and keep everything updated. New living room furniture Spring 2021. Completely renovated in mid 2020.

Guest favorite

Home in Berlin

5 out of 5 average rating, 10 reviews

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.

Superhost

A spacious outdoor deck is featured, offering views of Sunset Lake. Comfortable seating arrangements include a stylish couch and a small table with two chairs. Potted plants enhance the ambiance, while the lake's tranquil waters and a grassy expanse create a relaxing environment.

Vacation home in Wildwood Crest

4.88 out of 5 average rating, 41 reviews

Modern Waterfront 4-bedroom With Sunset Views

This stylish place to stay is perfect for group trips. Located in beautiful Wildwood Crest on the old Turtle Gut Inlet. Outdoor deck that looks right out onto Sunset Lake. Across from Sunset Lake park and 4 blocks from the beach . High quality furniture and appliances that are both aesthetically pleasing and functional. 1 King bed, 2 Queen beds, and 2 Twin beds make it perfect for a relaxing family vacation or a fun friendly getaway.

Top guest favorite

Cottage in Wildwood Crest

4.99 out of 5 average rating, 283 reviews

Bayfront home on Sunset Lake.

We are a 5 star rated Airbnb. We worked hard to earn that and harder to keep it. Our goal is to provide the cleanest and most beautiful experience in the Wildwood's. Beautiful sunsets every evening. Amenities include full kitchen, sub-zero refrigerator, dishwasher and all utensils. Washer and dryer included. Master bedroom with Queen bed and private tile shower. Living room with dining area. Both tv’s are smart, Hulu, Netflix etc.

Superhost

An oversized balcony features comfortable seating with blue cushions on wicker furniture. A small glass table is placed in between. The view includes water, boat traffic, and a nearby dock, all framed by the surrounding buildings and greenery.

Condo in Ocean City

4.88 out of 5 average rating, 211 reviews

Bayside Retreat in the Heart of Ocean City!

Newly renovated condo!! -Water view. Watch the boat traffic. -Oversized balcony with comfortable seating. -Comfy LoveSac couch. -Walk to boardwalk or beach - 15 minutes. -Walk to Jolly Roger amusement park. -Fish off community dock down below unit. -Close to dining and shopping. -Kitchenette for cooking meals. -Fast Wifi and Streaming TVs. -Fully Stocked Home. Clean linens, towels, toilet paper, paper towels & more!