Vacation rentals in Somerset County

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Top-rated vacation rentals in Somerset County

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Superhost

A warm interior space features a brick fireplace as the central focal point. Wooden paneling and a decorative ship's wheel add rustic charm. Natural light floods the area, highlighting the rich wood floors and creating an inviting atmosphere for gatherings.

Hotel room in Crisfield

5 out of 5 average rating, 3 reviews

The Cove - 9 Rooms and Conference center

Breathtaking summer, sunset view from the deck, overlooking Somers Cove Marina and the Little Annemessex River. Relax and enjoy the beauty of a small rustic town. In the heart of Crisfield MD - “The Crab Capital of the World” the Tyler family has owned and operated this property since 1980. This six bed, six bath whole house rental property is great for Family Reunions, Friends Get Together, Small Weddings, Business Meetings, etc. First floor is social area and bedrooms are on the second floor.

Top guest favorite

A spacious deck features several black Adirondack chairs arranged towards an expansive water view. The grassy area extends to the shoreline, creating a serene outdoor space. Light reflects off the water, enhancing the calm ambiance of the surroundings.

Home in Deal Island Historic District

4.97 out of 5 average rating, 59 reviews

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

Take it easy at this unique and tranquil getaway. Open floor plan home completely renovated in 2022. Surrounded by water on 3 sides with dock access and neighbors a community beach and boat ramp. Great place for fishing, crabbing, boating, jet skiing, kayaking or just relaxing by the fire pit. 3BR 2BA with florida room surrounded by large decks, full kitchen with quartz countertops, washer and dryer, sleeps 12, 1 queen BR, 1 Full BR, Triple Bunk BR, queen Sleeper, futon, and twin roll away bed.

Superhost

Cottage in Westover

4.87 out of 5 average rating, 69 reviews

Martha’s Cottage•at Old Beauchamp Homestead•

This quiet, charming, historic property is one of a kind! You won’t want to miss the opportunity to stay here! Martha’s Cottage is the perfect place to enjoy nature and its peaceful atmosphere. You simply won’t want to leave! A 30 minute drive to the Chesapeake Bay and about 45 minutes to Chincoteague Island! There is plenty of parking space to bring your boat! If you’re traveling with a group we can accommodate more guests in the adjoining “Mary’s Cottage” (check my profile for listing)

Superhost

A historic house stands nestled among tall pine trees, with a green roof and inviting porch visible. The clear blue sky enhances the serene outdoor setting, showcasing the property's natural surroundings and tranquil atmosphere.

Home in Princess Anne

4.83 out of 5 average rating, 24 reviews

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!

Top guest favorite

A custom-built cottage is nestled among tall grasses and trees, showcasing a charming two-story structure with a front porch. The backdrop features a mix of sunny skies and clouds, with marshland leading to a calm waterway on one side.

Cottage in Westover

4.99 out of 5 average rating, 220 reviews

Rumbley Cottage on the Tangier Sound-Private Beach

Winter time is a great time at Rumbley! Rumbley Cottage, a custom-built home, provides a quiet stay in nature. Views from all window. Look out to 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 Wifi, Molton Brown toiletries, kayaks, SPBs, bikes, beach equipment; well-stocked kitchen.

Top guest favorite

Cabin in Westover

5 out of 5 average rating, 44 reviews

Chalet Style Home, private country setting

Crooked Elm Cottage, nestled in Somerset County on Maryland's lower Eastern Shore, is ideal for outdoor enthusiasts. With easy access to the Chesapeake Bay and Atlantic Ocean, guests can enjoy birdwatching, hiking, fishing, boating, and biking, making it the ultimate base for adventure. Fully renovated, this charming retreat features a modern kitchen, a spacious living/dining area, high-speed internet, two expansive decks, and an outdoor recreation room complete with a pool table.

Guest favorite

A sandy beach area is visible, featuring a volleyball net with players engaging in a game. Sunbathers are relaxing on the sand and wooden benches, while a small building stands nearby. The calm water reflects a clear blue sky, creating a serene beach atmosphere.

Guest suite in Crisfield

4.75 out of 5 average rating, 203 reviews

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.

Guest favorite

Cottage in Westover

4.93 out of 5 average rating, 193 reviews

Heaven on the Bay - A Peaceful Waterfront Retreat

This Chesapeake Bayfront cottage has spectacular views to take you away from everything in any season. It boasts more than 120 feet of waterfront, and you can dangle your feet off the 70 ft “dock of the bay”. Launch kayaks from the small sandy beach in summer, or cozy up to the wood stove in the winter. Inside, you’ll find wood floors throughout, modern kitchen & baths with bay views from every room. Kayaks, SUP, bicycles & crab traps too!

Superhost

A serene beach scene features a wide stretch of golden sand meeting the calm waters under a clear blue sky. The shoreline curves gently in the distance, with sparse vegetation along the edges. Traces of footprints are visible in the sand, suggesting a tranquil area for walking.

Home in Saxis

4.86 out of 5 average rating, 138 reviews

ISLAND BREEZE Near Chincoteague Island

Waterman’s fishing village Surrounded by water on three sides & Virginia Wildlife Refuge on fourth side. Walking distance to beach (located on Dennis Lane) Kayaking & Canoeing Wildlife Fishing Pier Boat Ramp Marina Public Pavilion Ice Cream Shop 1-Restaurant (Capt E’s Hurricane Grill & Tiki Bar) Museum Multiple Seafood Shanty’s (Steamed Crabs Available during season)

Superhost

A modern waterfront home is surrounded by tall pine trees and lush grass. The structure features large windows that provide a view of the serene landscape and a deck that extends towards the water.

Home in Westover

4.94 out of 5 average rating, 33 reviews

Private beach with comfort

Relax with the whole family at this peaceful place to stay. Fantastic waterfront home.Your own very private location with your own sand beach. Perfect for family get away with water activities, swim,fish,Kayak etc.This home has a Handicap ramp and a Walk in shower with small curb for anyone who needs.

Guest favorite

A wooden boardwalk leads to a charming beach cottage, flanked by sandy beach and lush greenery. The cottage features large front steps, a light-colored exterior, and multiple windows offering views of the surroundings. The peaceful shoreline setting enhances the inviting entrance.

Cottage in Deal Island Historic District

4.95 out of 5 average rating, 82 reviews

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.