Cottage vacation rentals in Dorchester County

Amazing Bay Views Cottage W/Guesthouse & Hot Tub

Amazing property with fantastic water views, a hot tub and a fire pit surrounded by comfortable Adirondack chairs. This charming Cottage and separate Guesthouse offer a perfect blend of relaxation and adventure. Offering stunning Chesapeake Bay sunsets, beautiful pier for crabbing or fishing and a hot tub for soaking. Ideal for 2-3 couples or families, this pet-friendly fully fenced property sleeps up to 8 guests. A short 15 minute drive to Cambridge. Take day trips to Easton, St. Michaels.

Historic Home in Heart of Oxford, MD

Stay in a historic home built by the railroad when it came to town in 1880 (look for Pennsylvania Railroad memorabilia throughout the house!). Hardwood floors and fireplace with a yard on a quiet street, but in the heart of the historic bay town of Oxford, MD — half a block to the town market, coffee and ice cream, bookstore, and gift stores, and a block to the water on both sides of the house (enjoy beautiful sunrises & sunsets on the water!). Listed on the Natl. Registry of Historic Places.

Gettin to the point. ( Cove Point Beach)

Our beach house is for you to enjoy Cove Point Beach, which is only 500 ft away. The kitchen is fully stocked, or use the outdoor grill on the side of the house.PLEASE NON SMOKERS ONLY. One dog allowed on a cases by case bases with a one time pet fee of $65.00. No children under 8 years old. Walk to the beach, but only park your vehicle in our driveway, not on beach inlets. A gas fireplace in the living room. A beautiful sun porch area to enjoy. Enjoy walking on this private community beach.

Cozy Sunrise Waterfront Cottage & Dock

Experience tranquility at this true nature oasis, waterfront retreat adjacent to Point Lookout State Park! Start your day with coffee on the private dock, while bald eagles, herons, and ospreys soar above. Use our kayaks or paddleboard on the creek to relax onto a private beach or explore the open Chesapeake waters for top-tier rock fishing. Catch blue crabs with pots, stroll to the historic lighthouse, or enjoy swimming at the nearby public beach. Nature, adventure & serenity await you here.

Bay Beauty with boat slip & waterfront views!

Marvel at the breathtaking 360 views from every window throughout the house! The wraparound decks and private balconies are the perfect locations to take in the amazing expansive waterfront views in every direction! Stroll the 150’ boardwalk and enjoy the water views leading to a 200’ pier and 20’ x 20’ dock with boat slip for the avid boater. You will see nature all around you. Fish, crab or just relax off the dock while enjoying the spectacular views and most amazing sunsets!

Deal Island Bay Cottage - Maryland

Discover the charm of the Eastern Shore at the Deal Island Bay Cottage! Nestled on a spacious lot, it provides a peaceful escape with easy access to a Chesapeake Bay beach. Enjoy morning sunrises from the screened porch, Ideal for crabbing enthusiasts, the cottage includes local tips for the best spots. With high-speed WiFi and modern amenities, it’s perfect for both relaxation and remote work. Experience a true Waterman community and make lasting memories in this cozy retreat!

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!

Elk Cottage-Lake Lariat / Private lake access

If you are looking for nature, peace and relaxation close to the DMV area, then The Elk Cottage is all that and so much more. It is the perfect place, it is a waterfront property located in SoMD at Lake Lariat, and less than 10 minutes’ drive to the Solomon Islands. With the sounds of nature all around you. Enjoy your morning coffee with a great view of the lake, listening to the birds, watching the squirrels, the duck family and the lake turtles taking a sunbath.

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.

Riverside Haven w/ Hot Tub

Unplug and unwind at Riverside Haven, a cozy waterfront cabin for two overlooking the Chesapeake Bay. Dog-friendly and designed for comfort, it’s perfect for couples or solo travelers. Enjoy complimentary coffee, free Wi-Fi, a private hot tub, a fire pit and access to a small public beach next to the property. Wake up to stunning sunrises and relax in peaceful, natural surroundings—Riverside Haven is your perfect coastal escape.

Cottage on Cabin Creek

The cottage is the perfect getaway for couples. It is located on the water with two private piers for you to use. You may enjoy fishing, crabbing, kayaking, canoeing or bird watching from the piers. There is a charcoal grill available and a fire pit. The cottage is secluded enough for relaxation, but not far from local attractions and restaurants. Note the cottage is best suited for 1 to 2 people.

Charming Cottage in Tyaskin, MD

Charming New England salt box style cedar sided cottage directly across from Tyaskin Park. The Cottage is larger inside than appears on the exterior due to vaulted ceilings in the living room, kitchen/ dining areas. Beautiful views of the Nanticoke river from the living room, dining area and large deck. Pine flooring in all rooms with the exception of the tile floor bath and carpeted loft.