Pet-friendly vacation rentals in Somerset County

"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.

Walkability · Outdoor spaces · Family

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.

Pets · Outdoor spaces · Sleep quality

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.

Walkability · View · Family

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-in backyard where pets can roam freely and safely. With a dedicated workspace, it’s a perfect blend of relaxation and convenience.

Outdoor spaces · Pets · Getting around

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 -8 parking spaces -fully stocked kitchen -all linens and towels provided -screened porch with patio furniture -back deck with seating and grill -3 beach cruisers -4 beach chairs Things to do: fishing boating crabbing beach swimming kayaking and canoeing paddle boarding bird watching biking wildlife

Outdoor spaces · Grill · Access

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.

Pets · Outdoor spaces · Decor

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.

Outdoor spaces · Walkability · View

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.

Pets · Walkability · Biking

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).

Walkability · Pets · Long stay

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!

Pets · Walkability · Value

Rumbley Cottage on the Tangier Sound-Private Beach

September 12-16 available. 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. Many amenities: WE PROVIDE THE FIREWOOD AND STARTERS, kayaks, paddle boards, MB toiletries.

Pets · Outdoor spaces · Solo travel

Blue Crab Cottage: Remote+Nature+Fishing+Views

You’ll be anything but crabby after a relaxing stay in Blue Crab Cottage! This peaceful setting will chase your blues away. With three bedrooms to choose from –it's the perfect family getaway! Wingate Marina is 100 yards away and the house has ample parking for you to bring your own boat! Outdoor lovers enjoy this space to fish, kayak, and explore! Perfect for a remote family getaway in nature.

Walkability · Outdoor spaces · Backyard