
Holiday rentals in Deal Island Historic District
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Top-rated holiday rentals in Deal Island Historic District
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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.

Hideaway on the Bay: Waterfront Vintage A Frame
The Hideaway on the Bay is a waterfront A frame where you can disconnect from the things that can wait so you can connect with the people who matter most. A place where kids fall in love with nature, and where old friends make new memories. The house is a 2 bed 1 bath 1974 flat top A Frame that sits on two acres on the outskirts of Lusby, MD—and a low traffic hour(ish) drive from the DMV. Enjoy the indoor fireplace, outdoor fire pit, swinging chairs, kayaks, canoe, fish, and catch crabs --

Beach Front and 'Perfectly Placed'
Escape to our charming Potomac River waterfront cottage, complete with 2 cozy bedrooms, 1 tastefully appointed bathroom, and stunning river views. Enjoy a comfortable living area with large windows, a fully equipped kitchen, and an outdoor picnic table. Perfect for small families or friends seeking a peaceful retreat, our cottage is conveniently located just a short drive from local restaurants and shopping. Come relax, unwind, and make unforgettable memories on the beautiful Potomac River.

Peace Point - Waterfront, Secluded, Home w/hot tub
Take a break and unwind at this peaceful oasis. Very quiet, and secluded waterfront getaway is the perfect spot to relax with nature. House is located approximately 150 feet from the creeks edge providing amazing views. Located on a very quiet and unpopulated creek (no other houses) off the Chesapeake Bay, our home offers a scenic deck with hot tub, waterfront fire pit with seating for up to six people, private floating dock with kayaks to explore the scenic creek.

Blue Crab Bungalow
Our charming bungalow allows you to relax, refresh and truly unwind while taking in views of the bay. Enjoy amazing sunsets, lots of stars, and the water view from the 2nd story deck, private pier, or around the fire pit. Try crabbing or fishing from the pier. No license needed! A small local beach for swimming and public boat ramp are less than 5 minutes away. We are a little over an hour to Ocean City, Chincoteague, Assateague, and Blackwater Refuge.

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!

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. WE PROVIDE THE FIREWOOD AND STARTERS. Many amenities including Molton Brown toiletries, kayaks, SPBs, bikes, beach equipment; well-stocked kitchen.

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.

Private Beachfront Cottage with 2 Bedrooms + Loft
Relax and enjoy your own private beach with panoramic views of the Chesapeake Bay! Our cottage is in a quiet strip of Deal Island shoreline, but still boasts high speed internet - so you don't have to completely disconnect while you're here ...unless you want to, of course. We won't tell.
Popular amenities for Deal Island Historic District holiday rentals
Other great holiday rentals in Deal Island Historic District

Family Retreat - Private Pool, 4 Bedroom, Fire Pit

Waterfront Home w/ Private Dock, Beach & Fast WiFi

Chalet Style Home, private country setting

Waterfront Barn Loft with Modern Cabin Vibe

Private guest suite near Deal Island Maryland

Where the Road meets the Bay

House of the Setting Sun/Deal Island Bayfront Home

Cottage on the Creek
Destinations to explore
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- Chesapeake Bay
- Ocean City Boardwalk
- Ocean City Boardwalk
- Chincoteague Island
- Assateague Island National Seashore
- Assateague State Park
- Jolly Roger Amusement Park
- Breezy Point Beach & Campground
- Ocean Pines Golf Club
- Roland E Powell Convention Center
- Gerry Boyle Park
- Trimper Rides of Ocean City
- Calvert Marine Museum
- Salisbury Zoo
- Chesapeake Beach Water Park
- Chesapeake Bay Maritime Museum
- NASA’s Wallops Flight Facility Visitor Center
- Layton's Chance Vineyard and Winery
- Suicide Bridge Restaurant
- Baja Amusements
- Leonardtown Wharf
- General's Ridge Vineyard
- Belle Isle State Park





