Boat, Kayak and Paddle Board Rentals

Whatever types of water toys you are looking for Eastern Shore has them! Boat, kayak, and paddleboard rental options for the fish of the family and for the land lovers bike rentals.

For an added value, many of our homes include water toys such as kayaks and paddleboards.

Dockside Boat Rentals

Your "go to" in the area for boat rentals. Also offers bike, kayak, SUP, and jet ski rentals at their Oxford location.
Location: 104 W. Pier Street, Oxford, MD 21654
Phone: 410-971-2707

Easton Cycle and Sport

Rentals for bikes, kayaks, SUP`s and even Hobie Cats delivered to your vacation rental!
Location: 723 Goldsborough Street, Easton, MD 21601
Phone: (410) 822-7433

Shore Pedal and Paddle

Kayak, bike and SUP rentals. Delivery to your rental property or take advantage of their waterfront location in St. Michaels to enjoy a paddle in the harbor.
Location: 500 S. Talbot St, St Michaels, MD
Phone: 410-745-2320

Schnaitman`s Boat Rentals

Boat rentals on the Wye River, adjacent to the Wye Landing boat ramp.
Location: 12498 Wye Landing Ln, Wye Mills, MD 21679
Phone: 410-827-7663

Chester River Kayak Adventures

Kayak, SUP, and sailboat rentals in Rock Hall. Guided tours and sailboat packages available.
Location: 5758 N Main St, Rock Hall, MD 21661
Phone: 410-639-2001

Peloton Bike Rentals

Now offering Peloton Bike Rentals in select properties! If the newest fitness craze has you addicted to your bike, you can now still keep up with your goals and strive for your 100th ride while visiting the Eastern Shore. Cost: $250 per reservation, including set up and delivery Limited quantity available, first come, first serve basis Guest may be required to sign an additional waiver
Phone: 410-770-9093

TriCycle & Run

Outfitters for all swim, cycle and running needs. Frequently hosts free running events open to the public.
Location: 929 S. Talbot Street, St. Michaels, MD
Phone: 410-745-2836