Vacation rentals with a kayak in Somerset County

IDLEHOUR, 3 BEDROOMS 2 BATHS W/ DOCK

Unwind and relax after the busy life in the city. Get comfortable and enjoy plenty of extra space in this inviting retreat. Wake up refreshed and ready for a day of kayaking, bicycling and or exploring the island. Just four houses down, you'll find our deep-water dock--perfect for crabbing, launching kayaks, mooring your boat, or simply soaking in the peaceful surroundings. After a day of adventure, rinse off in our spacious hot and cold shower for a refreshing, nature inspired experience.

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.

Big Cozy Loft Overlooking the Farm and River

The Loft is located above the apiary workshop.  It is an expansive king room with bath.  Walk-in shower has a rainforest head. Views of the donkey pasture out your window!   From one side you have a view of the farm & river, the other apiary, gardens & river.  The loft is the perfect place to cozy up.  Each morning you will have a farm fresh breakfast.  The loft has a small refrigerator, tea, coffee with all your necessities. No WiFi/TV or smoking on property. No children in Loft.

The Hideaway

Welcome to The Hideaway, your serene waterfront retreat nestled on Maryland’s storied Eastern Shore. This modern coastal getaway is designed for ultimate relaxation, creative recharge, and inspired remote work — a short drive from anywhere in the DMV. Set directly on the glimmering Tangier Sound, this spacious 4-bedroom, 3-bathroom home features soaring ceilings, sun-drenched interiors, and thoughtful design that blends Scandinavian simplicity with mid-century warmth.

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.

Beachfront Chesapeake Bay Retreat

Welcome to our peaceful sanctuary on the Manokin River. Whether you're looking for a place to unplug and focus on connecting with family and friends, have some time to yourself or need a change of scenery for telework, Manokin House is the ideal retreat. The waterfront location allows you to truly enjoy the natural beauty of the Eastern Shore.

Private guest suite near Deal Island Maryland

Nothing extraordinary here. What I have available, at a reasonable rate is a clean private suite. With self check-in using kwikset smart code touchpad electronic deadbolt. Private driveway with plenty of room for your truck and boat. Room and deck are handicap accessible using entry ramp or steps.

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.

Rumbley Retreat

Welcome to our peaceful retreat on Goose Creek. Relax and unplug with family and friends, while enjoying beautiful waterfrontage. House comes with private dock across the street which allows you to dock your boat and truly enjoy being on the water! (**we now have WiFi)