Cottage vacation rentals in Dorchester County

Rodo Beach Cottage - Dog Friendly Private Beach wi

Free Wifi - Private Beach - Contactless Check-In - Pet Friendly - Tesla Charger - Linens, Soaps and Shampoo Provided. ****Summer weeks now booking only through ChesapeakeBayVacations (ig @ChesapeakeBayVacations)**** You'll feel like you're in your own world with the Chesapeake breeze as soon as you arrive at Rodo Beach Cottage. It's your very own beach front cottage to enjoy: * Crabbing off the pier * Biking around the Bay * Kayaks * Stand Up Paddle Boarding * Relaxing on the Hammock * P

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.

Mary’s Cottage•at Old Beauchamp Homestead•

This quiet, charming, historic property is one of a kind! You won’t want to miss the opportunity to stay here! Mary’s Cottage is the perfect place to enjoy nature and its peaceful atmosphere. You simply won’t want to leave! A 30 minute drive to Chesapeake Bay and about 45 minutes to Chincoteague Island There is plenty of parking space to bring your boat! If you’re traveling with a group we can accommodate more guests in the adjoining “Martha's Cottage” (check my profile for listing).

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.