Pet-friendly vacation rentals in Somerset County

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.

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.

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.

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 includes 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).

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.

Waterfront Historic Gem w/ Kayaks & Fire Pit

Experience the charm of The 1850 House, a 4-bedroom riverside getaway in historic Quantico, MD. Nestled along the Wicomico River, this pet-friendly retreat comes with kayaks, paddleboards, bikes, and a fire pit for outdoor adventures. Start your mornings on the furnished deck, explore nearby parks, beaches, and trails, or unwind in the screened porch and fenced yard. With a dedicated workspace, it’s a perfect blend of relaxation and convenience.

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!

One of a kind waterfront home with private dock

Beautiful 2 bedroom/1 bathroom waterfront getaway, with full kitchen and bath, loaded with amenities from coffee, cookware, charcoal grill to crabbing, fishing and kayaks. At the end of the day, gather around the backyard or take a walk down the 125+ foot pier for scenic views as the sun sets on the Wicomico River. Less than a 10 minute drive to the Red Roost and Bull Lips Dock Bar or head to Green Hill Country Club for a round of golf.

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.

Reel Relaxation-Waterfront

Reel Relaxation – A Waterfront Escape Nestled on Rock Creek in Chance, MD, Reel Relaxation offers stunning water views, a private dock, and a cozy fireplace. Unwind in the hot tub, gather by the fire pit, or enjoy fresh seafood on the screened porch. Kayak through Rock Creek. With three bedrooms, a pull-out couch, and modern amenities, this retreat sleeps up to 9. Whether fishing, grilling, or unwinding, it's the perfect escape.