Pet-friendly holiday rentals in Somerset County

Find and book unique pet-friendly homes on Airbnb

Top-rated pet-friendly home rentals in Somerset County

Guests agree: these pet-friendly homes are highly rated for location, cleanliness and more.

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Guest favourite

Home in Smith Island

4.95 out of 5 average rating, 19 reviews

Kayak friendly home on Chesapeake with golf cart

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.

Top guest favourite

Home in Smith Island

4.9 out of 5 average rating, 82 reviews

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!

Guest favourite

Home in Princess Anne

4.94 out of 5 average rating, 31 reviews

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.

Guest favourite

Home in Crisfield

4.97 out of 5 average rating, 65 reviews

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.

Superhost

Farm stay in Crisfield

4.73 out of 5 average rating, 15 reviews

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.

Superhost

Cottage in Deal Island

4.63 out of 5 average rating, 249 reviews

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!

Guest favourite

Cottage in Princess Anne

4.96 out of 5 average rating, 27 reviews

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!

Guest favourite

Cottage in Westover

4.99 out of 5 average rating, 236 reviews

Rumbley Cottage on the Tangier Sound-Private Beach

LAST MINUTE OPENING-09-27 to 10-03-25 !!!! 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.

Guest favourite

Farm stay in Princess Anne

4.95 out of 5 average rating, 111 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).

Top guest favourite

Home in Saxis

4.97 out of 5 average rating, 39 reviews

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.

Guest favourite

Home in Deal Island Historic District

4.95 out of 5 average rating, 37 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!

Superhost

Villa in Princess Anne

4.78 out of 5 average rating, 151 reviews

Waterfront Retreat & Guest House

Enjoy a relaxing private retreat with an amazing view of the water. Come to stay at the house the whole time enjoying sunsets, kayaking, building sand castles, playing in the water, and making great meals or venture to many nearby towns with great restaurants, hikes, golfing, breweries, bike paths, and more. Enjoy your own private 100 ft pier and sandy beach. **great wifi in main house and guesthouse