
Holiday houses in Deal Island
Find and book unique accommodation on Airbnb
Top-rated holiday 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.
FamilyLocationAccuracy

Soul Oasis - home on the Chesapeake Bay
Listen to the waves of the Chesapeake Bay from the trex deck. There are 2 private community beaches in the neighborhood where you can find fossils and sharks teeth. A great place to relax and unwind. You will hear the sounds of all kinds of birds, see lots of very tiny frogs in spring and summer and maybe some deer around the house! You can also expect to see/hear aircraft from Pax River Base fly overhead! Book your stay today and let the magic of the woods and water wash away your cares.
ValueLocationAccess

Marshall’s Retreat Chesapeake small town getaway
Modern 3 bedroom home centrally located in the heart of Crisfield, Md. Off & on street parking. Minutes from our towns new bike trail, boat & Kayak launch, park play ground,Wellington Beach, shopping, Ferry’s to The Islands, fishing piers, restaurants, Crab & Cruise (within walking distance), beautiful views. about an hour drive to Ocean City, Assateague or Chincoteague. Or stay in & relax watch Cable tv, Wifi. Please be sure to research the area online to make sure it’s right for your needs.
FamilyLocationWalkability

Eastern Shore Private Sandy Beach & Crabbing dock!
Marvel at the breathtaking 360 views from every window throughout the house! The wraparound decks and private balconies are the perfect locations to take in the amazing expansive waterfront views in every direction! Stroll the 150’ boardwalk and enjoy the water views leading to a 200’ pier and 20’ x 20’ dock with boat slip for the avid boater. You will see nature all around you. Fish, crab or just relax off the dock while enjoying the spectacular views and most amazing sunsets!a s n m
LocationFamilyKitchen

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
LocationFamilySleep quality

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!
FamilyValueComfort

Good Vibe Villa, Tiny houseboat
This tiny houseboat sits permanently on a boat lift, so you will have the unique experience of being over water without the risk of sea sickness! Located in the heart of quaint Solomons Island, this is a great stay if you love being near the water. Unparalleled views from your private porch. Please note, due to extensive pet damage we have changed this property to strictly no animals. You will be asked to leave if you arrive with a pet.
LocationFamilyQuiet

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.
LocationValueAir conditioning

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.
LocationValueAccess

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.
FamilyLocationCheckout

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.
ValueFamilyBackyard

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.
ValueFamilyAccuracy
Popular amenities for Deal Island holiday rentals
Other great holiday rentals in Deal Island

Waterfront Family Retreat• Private Dock • 5 BR
FamilyLocationBeach

La Cabaña
FamilyLocationOutdoor spaces

Reel Relaxation-Waterfront
LocationFamilyBathroom

Come enjoy Summer on Smith Island at the HH Ranch
LocationAmenitiesQuiet

Private guest suite near Deal Island Maryland
ValueFamilyWi-Fi

House of the Setting Sun/Deal Island Bayfront Home
ValueFamilyComfort

Cozy Crisfield Cottage
LocationFamilyHospitality

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





