Vacation rentals with lake access in Dorchester County

Where the Road meets the Bay

Picture a secluded open concept 3 bedroom house on an island overlooking the Chesapeake Bay. Elevated home with a wraparound deck offering panoramic views. Large windows flood the interior with natural light showcasing sunsets that paint the sky with vivid hues. A telescope is provided for bird watching & observing their daily activities. The tranquil sound of water lapping against the shore enhances the serenity. This is a retreat designed for peace, reflection, and awe-inspiring moments.

Historic St.Mary's City at the Lazy Bear Cottage

Inquire first on pets, there is a 50 lb. weight limit total, can be split up between 2 small dogs or 1 at 50lbs,,must be house broken and friendly. Close to Saint Mary's historic city, Pt. Lookout State Park, Sotterley Plantation. Great hiking trails, restored colonial village,a replica of the Maryland Dove. Tour a lighthouse. Great restaurants , or spend a day over in Solomons Island, about 20 miles from us. Peaceful settings for relaxing right on the water,or kayak on the river

Lakeside Cabin - Hot Tub, Firepit, Kayak, Arcade

Welcome to The Lake House, our updated 3BR/3BA waterfront cabin on Lake Vista with views of the Patuxent River and Chesapeake Bay from the private pier. Enjoy nearby Solomons Island, Calvert Cliffs, Flag Ponds, boating, fishing, hiking, and beaches, all within a short drive. Please note: This home is located in a quiet waterfront community surrounded by neighbors, nature, and wildlife. Sound carries across the water. No parties, events, gatherings, or excessive outdoor noise permitted.

Blackwater & Snakehead Farm "She Shed" Tiny House

The "She Shed" Tiny House is the best bargain & unique stay around! This Tiny House is made from a traditional 10'x18' shed and is solar powered! It's surprisingly spacious with a full size bathroom, kitchenette, lofted twin bed, day bed & trundle bed! The home borders a sheep pasture, barn, goat pasture & chicken coop! Snakehead fishing is just a short walk away! Kayacks & creek launch on site! Just a 5 minute drive from Blackwater Refuge! Relax and enjoy country living!

Spacious Gorgeous Waterfront Home with Sunset View

Dreamy weekends on the water, the perfect getaway for the entire family and friends in the southern tip of St Mary’s peninsula. This gorgeous newly remodeled house with 5 Bedroom 3.5 Bath sleeps 10 very comfortably. Wake up with amazing water views and access to the water with your own private pier. Spend your day crabbing, fishing, kayaking, or paddle boarding. Amazing beaches at Point Lookout State Park, just a few minutes away. High speed internet, WiFi, and cable.

Hoopers Island Retreat

Welcome to Hoopers Island retreat – a newly renovated coastal getaway with stunning waterfront views. This light-filled home features 3 bedrooms, 2.5 bathrooms, a full kitchen, spacious living area, and outdoor spaces made for relaxation—covered porch, hammock swings, sun loungers, dining set, and a private dock perfect for crabbing, kayaking (which are available at the property), or watching the sunset. A peaceful escape for families or friends to unwind by the water.

Epic Views, New Pier, Remodeled, Family & Pets

Waterfront 3BR/2BA home on 3 acres with remodeled kitchen and central brick fireplace. Master has CA king with water views; bedroom 2 has queen + crib; bedroom 3 has 2 twins (can combine into king). Multiple outdoor spaces include an expansive deck for stargazing, a screened porch with bench swing, and sprawling meadow views. Enjoy epic sunsets across the river, explore nearby trails, or relax near public piers. Entire home + garage included for privacy and comfort.

Peace Point - Waterfront, Secluded, Home w/hot tub

Take a break and unwind at this peaceful oasis. Very quiet, and secluded waterfront getaway is the perfect spot to relax with nature. House is located approximately 150 feet from the creeks edge providing amazing views. Located on a very quiet and unpopulated creek (no other houses) off the Chesapeake Bay, our home offers a scenic deck with hot tub, waterfront fire pit with seating for up to six people, private floating dock with kayaks to explore the scenic creek.

Stunning Chesapeake waterfront home

Spectacular new waterfront home in beautiful historic Oxford, comfortably sleeps 10 with perfect set up for 2 families. Enjoy Town Creek and Tred Avon water views from every room and angle. Gorgeous sunsets from the wraparound porch, stargazing and fishing from the dock. Walk to Morris Street for a relaxed coffee, stroll through Town Park, or take the Ferry to St. Michaels. The Town of Oxford has issued short term rental license # STR25-06 for this property.

Charming cottage, FP, 1 blk water, historic area

A peaceful oasis near the water in the center of Cambridge. Tucked away at the end of a cul-de-sac with historic connections, this private, charming antique-filled cottage is steps away from the river. Enjoy three comfortable bedrooms all with en-suite bathrooms, and 2 living areas w/ fireplace and view of the Choptank River, with plenty of room for family and friends to entertain. Close to all amenities, Gerry Boyle Park and the waterfront.

Waterfront Oasis! Hot tub! 2+ acres - Sleeps 8

HOT TUB!! WATERFRONT!! Relax with the entire family at this peaceful 3 bedroom fully remodeled private waterfront cottage on a quiet cove off the Choptank River/Chesapeake Bay. Enjoy the incredible views from your bed, from the large screened-in porch, from the oversized deck, from the hammock or double swinging chair out by the water! Launch a kayak right from the property and watch the gorgeous sunrises from the comfort of your bed!

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.