
Holiday rentals in Somerset County
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Top-rated holiday rentals in Somerset County
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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.

5 bedroom waterfront retreat with private dock
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.

Peaceful Home Away from Home
Take a break and unwind at this peaceful home...or take advantage of the convenience to outdoor Eastern Shore activities. Conveniently close to crabbing, boating and fishing, this home provides peace and quiet while steps away from the joys of country living. Whether you're in town for the Skipjack Races in Deal Island, MD or graduation at HBCU, UMES, we are close enough to "town" but yet far enough from the hustle and bustle of town living. Travel Healthcare Professionals are welcome.

Home of The Terrapin King
The LaVallette House is where the Maryland terrapin originated! Albert Tallmadge LaVallette Jr. launched the terrapin soup industry from this very site in 1887 (you can still see the old terrapin pins beside the driveway). In addition to the property’s historic charm, the location just can’t be beat. The five-bedroom house is completely private. Guests have to drive through wetlands to get to it, and the only neighbors in close proximity are the gulls and the fish in the Chesapeake Bay.

Waterfront Cottage in Mt. Vernon
Relax with the whole family at this peaceful place to stay. Whether getting away for a weekend or visiting near by family there is enough room for all. With a large deck space facing the Wicomico River, you can enjoy outside time with family while each of you has something to do. There is a queen bed, queen pull out couch, and twin to king trundle bed sleeping six! Each stay inlcudes free wifi and parking, kitchen with full amenities, grill, beach, dock use, fishing and more!

Farmhouse located on a horse farm
Farmhouse located just minutes off of Route 13 in Princess Anne, MD. Enjoy a peaceful farm experience while staying in a charming farmhouse with lots of character. You can walk the grounds of the farm, including a trail through the woods, or take a swim in the pool. We do not offer horseback riding lessons but you can interact with the horses. We are minutes to shopping, groceries, restaurants, UMES, and a short ride to Chincoteague (32 miles) and Ocean City (40 miles).

Cozy Home near Waterfront in Crisfield, MD
Our home is close to great views, restaurants and shopping, the beach and family-friendly activities. You’ll love the sunsets over the water and viewing working boats in the harbor. Great for couples, solo adventurers, business travelers, and families (with kids). Beach is walking distance and the boat launch is 1/2 mile away. New library, playground, fishing, crabbing and gorgeous sunsets are all close by. Owners live only 15 minutes away for anything you may need.

Marsh View Saxis
We love this home and we hope you will as well, offering a perfect blend of comfort and style with 3 bedrooms and 2 bathrooms, breathtaking views of the wetlands, where sightings of graceful blue herons await you. Step into the spacious living area, where natural light floods the beautiful and bright open kitchen. The large yard surrounding the house provides a serene setting, great for relaxation and outdoor activities including a fantastic firepit.

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.

ISLAND SUNSETS Near Chincoteague Island
1 - Story Near Chincoteague Island Virginia Assateague Beach NASA Wallops Island, Va. Onancock, Va Waterman’s Fishing Village Surrounded by Water on three sides & Virginia Wildlife Refuge on fourth side. 400 ft. Walking distance to Beach, Kayaking & Canoeing, Wildlife, Fishing Pier, Boat Ramp, Marina, Public Pavilion, Ice Cream Shop, 2 Restaurants, Museum, Multiple Seafood Shantys
Popular amenities for Somerset County holiday rentals
Other great holiday rentals in Somerset County

The Hideaway

Heaven on the Bay - The Perfect Coastal Cottage

Private guest suite near Deal Island Maryland

One of a kind waterfront home with private dock

Crisfield Cabin by Homelystay

Cabin with History On a historic 18acre homestead

Dog-Friendly Westover Cottage w/ River Access!

Smith Island Yummy Artist Retreat
Destinations to explore
- Chesapeake Bay
- Ocean City Beach
- Ocean City Boardwalk
- Assateague Island National Seashore
- Assateague Beach
- Haven Beach
- Jolly Roger Amusement Park
- Northside Park
- Bayside Resort Golf Club
- Jolly Roger at the Pier
- Assateague State Park
- Plantation Lakes Golf and Country Club
- Piney Point Beach
- Ragged Point Beach
- Heritage Shores
- Splash Mountain Water Park
- Wallops Beach
- Snead Beach
- Sandyland Beach
- Ocean Pines Golf Club
- Gerry Boyle Park
- Guard Shore
- Oxford Beach
- St George Island Beach




