Pet-friendly vacation rentals in Somerset County

4.9 out of 5 average rating, 82 reviews

A cozy bed is adorned with soft pillows featuring marine-themed designs, complemented by a light-colored duvet. Behind the bed, a decorative wall with muted colors showcases artful textures. Natural light filters in through nearby windows, enhancing the calming atmosphere of the space.

Home in Smith Island

Smith Island Yummy Artist Retreat

I believe in actually having an experience when travelling! Be comfortable while experiencing life thru the eyes of an artist. The house has the flavor of island life. Windows that catch breezes and airy spaces that feel welcoming. I am a resident artist also living both in MD and NJ. I have created my home without limitations! I am continually expanding and developing the spaces to be alive and fun. Ferries leave Crisfield MD at 12:30pm to come to island. Sunday ferries sept-may are iffy!

4.96 out of 5 average rating, 27 reviews

A modern kitchen features a central island with a bright countertop and a small plant centerpiece. Stainless steel appliances line the walls, complemented by light-colored cabinetry. Natural light enters through sliding glass doors, while stylish pendant lights hang above the island.

Home in Princess Anne

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.

4.97 out of 5 average rating, 64 reviews

A light-colored couch with striped black and white pillows is positioned in a spacious living area. A round, dark wood coffee table sits in front of the couch, accompanied by a soft area rug. Natural light enters through two nearby windows, illuminating the room.

Home in Crisfield

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.

4.69 out of 5 average rating, 13 reviews

Farm stay in Crisfield

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.

Home in Deal Island Historic District

A dock extends over calm waters, framed by a vibrant sunset showcasing hues of orange and purple. A picnic table is positioned on the dock, and a flag gently flutters nearby, enhancing the peaceful scene.

4.85 out of 5 average rating, 39 reviews

House of the Setting Sun/Deal Island Bayfront Home

Soak up the quiet beauty of Tangier Sound at this bayfront getaway with stunning sunset views among the pines. Enjoy crabbing, fishing, and swimming off the dock. Dive into nature photography, birdwatching, hunting, kayaking in the wetlands, and more. There's a small local beach less than 5 minutes away. It's far enough away to unplug, but less than an hour to Ocean City, Chincoteague, and Assateague. And there's plenty to enjoy onsite, including sunsets 9 months out of the year!

4.63 out of 5 average rating, 246 reviews

Two chairs are positioned on sandy ground, facing a tranquil bay at sunset. Fishing poles stand upright in the sand beside the chairs, while soft waves reflect shades of orange and pink from the sky. A grassy area frames the scene, enhancing the peaceful atmosphere.

Cottage in Deal Island

Deal Island Bay Cottage - Maryland

Discover the charm of the Eastern Shore at the Deal Island Bay Cottage! Nestled on a spacious lot, it provides a peaceful escape with easy access to a Chesapeake Bay beach. Enjoy morning sunrises from the screened porch, Ideal for crabbing enthusiasts, the cottage includes local tips for the best spots. With high-speed WiFi and modern amenities, it’s perfect for both relaxation and remote work. Experience a true Waterman community and make lasting memories in this cozy retreat!

5 out of 5 average rating, 25 reviews

A wooden deck is shown with a round table and four black mesh chairs, facing the calm waters of the Wicomico River. Lush greenery surrounds the area, with a dock visible in the background. The sky features soft clouds, enhancing the serene atmosphere.

Cottage in Princess Anne

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!

Farm stay in Princess Anne

The farmhouse features a white exterior with green roofing. A welcoming porch is flanked by well-maintained landscaping, including shrubs and garden stones. Large windows allow natural light to enter, while the chimney adds character to the overall rustic appearance of the home.

4.94 out of 5 average rating, 109 reviews

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).

4.97 out of 5 average rating, 38 reviews

An outdoor firepit area features a circular stone patio surrounded by six blue chairs. The fire burns brightly at the center, set against a backdrop of lush green grass and wetland vegetation, with overcast skies above.

Home in Saxis

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.

Home in Deal Island Historic District

4.94 out of 5 average rating, 35 reviews

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!

4.99 out of 5 average rating, 233 reviews

An aerial view highlights Rumbley Cottage's proximity to the shoreline and wetlands. The landscape features a mix of sandy beach, shallow waters, and expansive marshlands under a clear blue sky, offering a serene setting with natural beauty and tranquility.

Cottage in Westover

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.