Holiday rentals with lake access in Dorchester County

Hot Tub Hideaway by Shark Tooth Shores

With views of the Chesapeake Bay, access to private beaches, a brand new hot tub, air hockey table, kayaks, and being just minutes away from hot spots like Calvert Cliffs and Solomon's Island the Hollow makes for the perfect vacation destination. Enjoy sunrise views through the treetops each morning on the expansive back deck, or use our eco-friendly wood burning stove for autumn and winter nights. Unlike many beach houses, this home is surrounded by trees making it serene. UPDATED PHOTOS SOON

Blackwater Tiny Cabin on Snakehead Creek

The Solar Powered Tiny Cabin is located on a farmette, making your visit even more memorable! Just a 5 min drive from Blackwater Refuge! It's an affordable and unique way to visit and enjoy all that Cambridge and Blackwater Refuge have to offer! The Tiny Cabin is located steps away from Pitcher Dam Creek, leading to Little Blackwater! Kayaks on site! Bring your fishing rod to catch Snakeheads! 15 minute drive to Route 50, downtown Cambridge, shopping and dining! *BOOKING PARTY MUST BE 21 yrs+

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.

Cozy Tiny House at Snug Harbor Marina

Escape to this cottage located at Snug Harbor Boat Ramp. Perfect for boaters, couples, and anyone looking for a peaceful waterfront getaway, this cozy retreat offers easy access to the water. The space features an open-concept living area, a kitchenette, and bedroom. Outside, relax on the porch with your morning coffee while enjoying the surroundings. The boat ramp is just steps away, making it easy to launch your boat, spend the day fishing, or explore the beautiful waterways nearby.

Magical Waterfront Home Dock, Firepit, Family Fun!

Heron's Rest is a stunning home w/ arguably the best water views in Cambridge from nearly every room, expansive patio, fire pit and dock - a peaceful place to gather with family and friends. Incredible location to explore the stunning and historic Eastern Shore and charming historic Cambridge. Easy drive to the Atlantic beaches--you CAN have it all- kayak, fish, birdwatch, explore Blackwater Wildlife Refuge, Easton, St. Michael's. Rare location w sunset and sunrise views!

Adorable Waterfront Apt Weekend Getaway & Scones!

Bright & cheery 1 bedroom waterfront apartment nestled on the banks of the St. Mary's River. Amazing, dreamy views. It's a sweet spot to relax and enjoy a quiet get-away or launch a kayak, take a walk, enjoy great cuisine. We sit next to St. Mary's College of MD and Historic St. Mary's City. You may see college sailing races, crew teams rowing, or the historic Maryland Dove sailing down the river. It's lovely here year around! SUNSETS! Enjoy our Homemade SCONES too!!

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.

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 is about 20 miles north of us Great hiking trails at the college. Tour a lighthouse. Great restaurants , or spend a day over in Solomons Island, about 20 miles from us. Check out Calvert Cliffs or Annemarie Gardens in Solomon's area

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.

Waterfront Barn Loft with Modern Cabin Vibe

Relax in nature for a while in our beautiful and cozy barn loft. The loft is located next to our primary residence on 7 private acres along scenic Rewastico Creek, offering year round beauty. Kayak on, or relax by, the tidal marsh creek which is fed by the Nanticoke River and Chesapeake Bay. Centrally located between popular Eastern Shore destinations such as Atlantic beaches and historic small towns. A serene oasis with abundant wildlife.

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!

Cozy Lakeside Studio Retreat.

Cozy basement studio that provides a perfect get away. From beach combing, kayaking, fishing, swimming in the Bay, relaxing on the dock, building a fire in the backyard pit, and corn hole, there’s lots to do. Or simply just relax and enjoy the serene surroundings. Photography package available, message host for details 2 GUESTS ONLY; please check with host regarding children