
House vacation rentals in Somerset County
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Top-rated house rentals in Somerset County
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Come enjoy Summer on Smith Island at the HH Ranch
Relax in this 1910 era Smith Island home. Has one large upstairs bedroom with second twin bed separate from main bedroom. Comfortable family room with seating for 5. Updated enclosed patio is ideal in the summer. Large kitchen fully stocked to cook your meals. New front deck. Large bathroom with dual rainhead shower. Easy access to the water. Bikes and SUP available in the shed. Kayaks are covered outside by shed. Island is only accessible by boat. Enjoy the tranquility of this unique place.

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.

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.

Kayaker and Fisherman's Pit Stop
Take a break and unwind at this peaceful old farm home. Built in the 1920s, this five-bedroom house awaits those who do not need a luxurious stay. It has three bedrooms with air conditioners, a washer and dryer on the premises, and plenty of parking in the back. Great for those who want a place to shower, get a good night's rest, and make a meal in the renovated kitchen with modern appliances before getting back on the water. It's a five-minute walk to the river where you can fish and kayak.

Ye Ole Pirate House
Legend has it that this whole unique area was once inhabited by pirates! Surrounded by nature, not to mention the starry sky at night, this house is the embodiment of the life and spirit of all that have been fortunate enough to experience the tranquility and beauty this area offers. Our home here is spacious and quiet! Surrounded by nature, trees, nearby beach to enjoy sunsets and best of all the simple songs of the birds. Bring your fishing pole, boat ,kayak , yoga or meditation mat!

Countryside Home in Princess Anne
Escape to tranquility at our private home in the serene countryside. Our spacious and comfortable three-bedroom, two-bathroom home provides ample space for families, couples, and groups of friends to relax and enjoy the outdoors. Relax in the cozy living area, cook a meal in the fully equipped kitchen, or enjoy an evening around the campfire. With comfortable bedrooms and a peaceful location, it's the ideal getaway for a relaxing break. Book now and experience the beauty of rural living!

Catch of the Bay
Welcome to the completely remodeled catch of the bay cottage! You will enjoy calling this beachy yet rustic location with a farmhouse theme your home during your stay. The home offers three bedrooms and one bathroom - one king bed, one queen bed, and a set of bunkbeds. There’s also a pull out couch if that more so meet your needs. The home offers a remodeled and fully stocked kitchen, laundry area/mudroom on the inside, as well as a spacious backyard, fire pit in front and rear porches.

Island Time (whole house rental)
3 story home with 2 wrap around porches. One first floor room and three second floor rooms-including a master suite. The third floor is a loft with sleeping for 5 and a full bath. Breathtaking views of sunrises and sunsets. Life on the island is laid back. Visit us to get away from the fast pace life. We offer complimentary bikes, kayaks, fishing poles, crab nets, porch swings, hammock, hot tub, etc. Golf Carts available for rent. Breakfast and STEAMED CRABS are available for a charge.

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

Marsh View Saxis
With 3 bedrooms and 2 bathrooms, this home offers a perfect blend of comfort and style — and a view you won't get tired of. Watch graceful blue herons wade the wetlands right from your window. Inside, natural light floods the spacious, open living area and kitchen. Outside, the large yard is made for relaxing, with plenty of room to spread out and a fantastic firepit for evenings under the stars.

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 Somerset County house rentals
House rentals with a pool

1 Mi to Boat Ramp: Peaceful Deal Island Home!

Kingsbay Mansion Bayhouse

Creek House | Luxury Waterfront + Resort Pool

The Porter's Barn | Waterfront w/ Dock + Fire Pit

Kingsbay Dockside Waterfront House

Condo-The Oasis on the Bay
Weekly house rentals

The Hideaway

Casa Del Rio by Seaside Vacations & Sales

Vacation home near the beaches

Country House on Wicomico Creek

Smith Island Spectacular Sunsets!

Hummingbird Cottage

Beautiful Bayfront with Sanctuary Private Beach

Where the Road meets the Bay
Private house rentals

Ruarks Watermen's Refuge

The Pirates House Lands End

Island Voices In The Wine Near Chincoteague & NASA

Skipper's Retreat

Maryland Retreat: Walk to Bay, Beach & Boat Ramp!

Rusty Anchor

Waterfront Retreat with Private Beach, Dock & Lift

Island Jewell Near Chincoteague
Destinations to explore
- Chincoteague Island
- Chesapeake Bay
- Assateague Island National Seashore
- Ocean City Beach
- Assateague State Park
- Northside Park
- Jolly Roger Amusement Park
- Roland E Powell Convention Center
- Ocean Pines Golf Club
- Ocean City Boardwalk
- Gerry Boyle Park
- Old Pro Golf
- Trimper Rides of Ocean City
- Salisbury Zoo
- Leonardtown Wharf
- NASA’s Wallops Flight Facility Visitor Center
- Splash Mountain Water Park
- Suicide Bridge Restaurant
- Layton's Chance Vineyard and Winery
- General's Ridge Vineyard
- Jolly Roger at the Pier
- Calvert Marine Museum
- Ocean City Boardwalk





