Vacation rentals with a kayak in Somerset County

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.

5 bedroom waterfront retreat with private dock

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.

Heaven on the Bay - The Perfect Coastal Cottage

This Chesapeake Bayfront cottage has spectacular views to take you away from it all in any season. Watch the sunrise & sunset everyday! It boasts more than 120 feet of waterfront, and you can enjoy time on the 70 ft. dock! Launch kayaks & SUP from the small sandy beach in summer, or cozy up to the wood stove in the winter. You’ll love the quaint cottage feel, modern kitchen & baths, with stunning bay views from every room. Kayaks, SUP, bicycles & crab traps too. Your peaceful retreat awaits!

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.

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!

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.

Michele's House, Pet-Friendly, Sleeps up to 12

Only accessible by ferry, one of only rental homes with Wifi and landline. Pets welcome with additional fees. Michele's House is a Smith Island Inn Cottage. The home has a ramp and the main level is wheelchair accessible. The 3 bedroom, 2 full bath Cape Cod sleeps the most guests of any rental on the Island, up to 12. The coastal décor extends throughout the home. A large living room area, two dining spaces, back deck with chairs and an open floor plan welcomes guests.

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.

Big Cozy Loft Overlooking the Farm and River

Located above the apiary workshop, the Loft is a spacious kind suite with a walk-in bath featuring a rainforest shower. Windows overlook the donkey pasture, river, farm, and gardens, Each morning, a farm-fresh breakfast is delivered. The Loft includes a small refrigerator plus coffee and tea essentials. Designed for a true retreat, there is no WiFi, TV, or smoking. Please note: children are not permitted.

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.