
Vacation rentals in Deal Island
Find and book unique accommodations on Airbnb
Top-rated vacation rentals in Deal Island
Guests agree: these stays are highly rated for location, cleanliness, and more.

The Tangier Escape
Looking for a relaxing getaway, or duck hunting or fishing lodging ? This coastal themed home is located in a quiet crabbing village on Deal/Wenona Island MD The house has 2 bedrooms UPSTAIRS which has a King size bed in one room and then a Queen size bed in the other. . Downstairs, there is a sofa bed that is a queen size pullout bed. There is a fully equipped kitchen with a griddle and a large pot for cooking fresh crabs in. There is also a grill to cook up any fish caught that day.

Waterfront Family Retreat• Private Dock • 5 BR
Welcome to Moonacre Bay! Nestled between Teague Creek and the mouth of the Manokin River, this house offers breathtaking views from every room. Enjoy peaceful sunrises over the marsh from the front porch swing. In the evenings relax on the expansive, screened in deck to watch the sun go down over the Bay. With a fully stocked kitchen, comfortable living areas, a serene office space, and fast-paced internet, Moonacre Bay has all the comfort and amenities to make this your home away from home.

Deal Island Lodge
Recently renovated 1960's farmhouse located in an authentic watermen's community. -pets allowed - with approval prior to check-in -very clean, quiet, cozy and relaxing -use of entire home -6 parking spaces -fully stocked kitchen -all linens and towels provided -screened porch with patio furniture -picnic table -3 beach cruisers -3 beach chairs Things to do: fishing boating crabbing beach swimming kayaking and canoeing paddle boarding bird watching biking wildlife

The Serenity House
Regenerate at the Serenity House! Second floor apartment; three spacious queen bedrooms with SmartTV, equipped kitchenette, work space with WiFi, mudroom and laundry on the first floor. Large yard with big mature shade trees nestled in a quiet neighborhood. One corgi and two cats live on the property. The pets are not allowed into the guest rooms. Continental breakfast served in the shared space. Private entrance, off street parking available.

Rusty Anchor
Escape to the Rusty Anchor, a beautifully restored 1900s farmhouse on Deal Island, MD! With 3 cozy bedrooms, it's perfect for families or friends. Just around the corner, enjoy a cozy beach, crabbing, and easy access to fishing (Redfish, Striped Bass, Flounder) and waterfowl hunting. Only a 5-minute bike ride to beaches and boat ramps. Book now and receive a link to our store to reserve add-ons or schedule special experiences for your stay!

Reel Relaxation-Waterfront
Reel Relaxation – A Waterfront Escape Nestled on Rock Creek in Chance, MD, Reel Relaxation offers stunning water views, a private dock, and a cozy fireplace. Unwind in the hot tub, gather by the fire pit, or enjoy fresh seafood on the screened porch. Kayak through Rock Creek. With three bedrooms, a pull-out couch, and modern amenities, this retreat sleeps up to 9. Whether fishing, grilling, or unwinding, it's the perfect escape.

Blue Crab Cottage: Remote+Nature+Fishing+Views
You’ll be anything but crabby after a relaxing stay in Blue Crab Cottage! This peaceful setting will chase your blues away. With three bedrooms to choose from –it's the perfect family getaway! Wingate Marina is 100 yards away and the house has ample parking for you to bring your own boat! Outdoor lovers enjoy this space to fish, kayak, and explore! Perfect for a remote family getaway in nature.

Rumbley Cottage on the Tangier Sound-Private Beach
Rumbley Cottage, a custom-built home, provides a quiet stay in nature. Views from all windows. Look out at the mouth of the Manokin River at Tangier Sound on one side; wetlands on the other side. NO CLEANING OR PET FEE. Rumbley Cottage is enjoyed year- round with a great fireplace. Many amenities: WE PROVIDE THE FIREWOOD AND STARTERS, kayaks, paddle boards, MB toiletries.

Highbanks House
Forget your worries in this spacious and serene space. Welcome to your dream home! This stunning 5-bedroom, 3-full-bath rancher is nestled on over 6 acres of private land, offering a perfect blend of comfort and nature. Located just 6 miles from downtown Salisbury and 8 miles from Salisbury University, this property provides both tranquility and convenience.

Levering Creek Cottage with private dock
Levering Creek Cottage is a waterfront property with a deep water dock that you can see from the back door. We are located on Levering Creek where you can sit on the dock watching watermen arrive with their daily catch, see nesting bald eagles, watch beautiful sunrise, fish and crab. We are also just steps away from most everything including the ferry.

Island Oasis, Tangier Island, Virginia
Island Oasis is a one story, waterfront, newly renovated home situated in the heart of town. The tour boat docks are directly behind property with a gift shop on site. Restaurant, ice cream/sandwich deck, grocery store, church, museum , etc are all within walking distance. Guests will have full access to home and a nice deck overlooking harbor.

Beachfront Chesapeake Bay Retreat
Welcome to our peaceful sanctuary on the Manokin River. Whether you're looking for a place to unplug and focus on connecting with family and friends, have some time to yourself or need a change of scenery for telework, Manokin House is the ideal retreat. The waterfront location allows you to truly enjoy the natural beauty of the Eastern Shore.
Popular amenities for Deal Island Historic District vacation rentals
Other great vacation rentals in Deal Island

Ye Ole Pirate House

"Promise Point" Bay front home with dock. 3BR 2BA

Eastern Shore Private Sandy Beach & Crabbing dock!

Island Time (whole house rental)

Peaceful Home Away from Home

Cozy Crisfield Cottage

Waterfront Historic Gem w/ Kayaks & Fire Pit

Nature retreat with water view
Destinations to explore
- New York Vacation rentals
- Philadelphia Vacation rentals
- Washington Vacation rentals
- Ocean City Vacation rentals
- Pittsburgh Vacation rentals
- Virginia Beach Vacation rentals
- Raleigh Vacation rentals
- Jersey City Vacation rentals
- Wilmington Vacation rentals
- Newark Vacation rentals
- Baltimore Vacation rentals
- Richmond Vacation rentals
- Chincoteague Island
- Chesapeake Bay
- Assateague Island National Seashore
- Assateague State Park
- Jolly Roger Amusement Park
- Breezy Point Beach & Campground
- Roland E Powell Convention Center
- Ocean Pines Golf Club
- Ocean City Boardwalk
- Gerry Boyle Park
- Calvert Marine Museum
- Salisbury Zoo
- Trimper Rides of Ocean City
- Chesapeake Beach Water Park
- Chesapeake Bay Maritime Museum
- Leonardtown Wharf
- NASA’s Wallops Flight Facility Visitor Center
- Suicide Bridge Restaurant
- Layton's Chance Vineyard and Winery
- General's Ridge Vineyard
- Ocean City Boardwalk
- Splash Mountain Water Park
- Jolly Roger at the Pier





