Vacation rentals with lake access in Dorchester County

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 or less,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.

Spacious and private waterfront, sleeps 10

Are you looking for a family getaway or a peaceful location to telework? This property offers it all. Tastefully remodeled waterfront property with a large private salt water pool, dock for fishing, crabbing and kayaking. One-floor open plan with two large decks. Great for entertainment in privacy and is in proximity to restaurants, vineyards, beautiful beaches and parks of Chesapeake Bay and Patuxent River. Just 1 hour to the south of Washington DC and within minutes to NavAir base and Excelon

Madison Bay Club House

Your own private 190' pier. Bring your boat and the family to this peaceful place to stay. Located on the water on Madison Bay, south of Cambridge. The laid back idyllic rural fishing village will make you immediately relax. Bay views from every room. Beautiful sunsets. Your own beach to relax or launch kayaks. A bird watchers paradise location with cultural and historical significance close by. A short drive to Blackwater National Wildlife Refuge and the Harriet Tubman birthplace and museum.

Lakeside Cabin - Hot Tub, Firepit, Kayak, Arcade

Welcome to The Lake House - our freshly updated 3 bedroom, 3 bath cabin on Lake Vista with views of the Patuxent River/Chesapeake Bay from the private pier. Enjoy everything Southern Maryland has to offer all within a 10 minute drive - Calvert Cliffs, Flag Ponds, Solomons Island - hiking, fishing, boating and beaches. Located just 90 minutes outside DC, The Lake House will become your new go-to retreat from the hustle. Come relax and make memories on the water with your family and friends.

1 bed/din./kitchenette Waterview SolomonsMDprivate

LowerFL.Self-contained, unobstructed BayView and beach access. Fast WiFi. Drumpoint beach & a lake are 2 houses away.Guests are welcomed to use Drumpoint club amenities. groceries, pharmacy, restaurants are nearby.Well water. You may hear jets fm NSVAIR.Loud noises, Smoking & illegal drugs are prohibited. Security cameras are installed. Pet allergies is a serious concern.$500 fee will be charged for smoking inside, carpet stains and pet damage.Pets need to get approved.IDs are required.

Driftwood Haven, Chesapeake Bay views throughout

Driftwood Haven is a charming updated cottage with unparalleled views of the Chesapeake Bay from nearly every room! Relax on the screened-in porch, or dine al fresco in the outdoor space equipped with a grill, swing, and fire pit. Perfect for families or groups, this retreat offers a blend of comfort and natural beauty. Enjoy easy access to two private community beaches: Driftwood Beach (2 min drive) and Seashore Beach (9 min drive). Lake Lariat is a short 6 min. drive away.

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.

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.

Adorable Waterfront Apartment Weekend Getaway

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 food 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 fall, winter, spring, summer! SUNSETS!

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!