Cottage holiday rentals in Dorchester County

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Top-rated cottage rentals in Dorchester County

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Guest favourite

Cottage in Cambridge

4.98 out of 5 average rating, 51 reviews

Cozy Cottage on the Bay

Relax and unwind at our 2 acre waterfront cottage. Enjoy the private dock, kayaks, fire pit, front porch, or back deck! Known for excellent fishing, crabbing, hunting, and boating. The tiny city of Cambridge is rich with history, has maintained its charm and adds tasteful local shops/eats. Public boat ramp 3 miles away Hyatt Regency Golf Course and Spa Resort (15min) Adorable Easton/ St. Michaels (30min) Nearby Blackwater National Wildlife Refuge is 28,000 acres ideal for the outdoors man/woman

Guest favourite

Cottage in Scotland

4.95 out of 5 average rating, 40 reviews

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

Top guest favourite

Cottage in Lusby

4.98 out of 5 average rating, 280 reviews

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.

Superhost

Cottage in Scotland

4.91 out of 5 average rating, 45 reviews

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.

Guest favourite

Cottage in Cambridge

4.98 out of 5 average rating, 49 reviews

Cozy 3-bedroom cottage steps away from the water.

Step out the front door to take in the view of and feel the refreshing breeze off of the Choptank River. Built in the late 1800s and nestled in Cambridge's Historic District, our home is a perfect mix of original architectural character and modern upgrades, and a short walk to the Marina, historic monuments, and downtown which is lined with restaurants, boutiques, galleries and so much more. You will be close to everything Cambridge has to offer when you stay at this centrally-located home.

Guest favourite

Cottage in Princess Anne

4.97 out of 5 average rating, 29 reviews

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!

Top guest favourite

Cottage in Westover

4.99 out of 5 average rating, 238 reviews

Rumbley Cottage on the Tangier Sound-Private Beach

LAST MINUTE OPENING-09-27 to 10-03-25 !!!! 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.

Top guest favourite

Cottage in Woolford

5 out of 5 average rating, 79 reviews

Waterfront Cottage & Guesthouse Near Cambridge

Escape to a serene waterfront oasis just 15 minutes from Cambridge on Maryland's picturesque Eastern Shore. This charming Cottage and separate Guesthouse offer a perfect blend of relaxation and adventure, with stunning Chesapeake Bay sunsets, direct water access, and modern amenities for an unforgettable getaway. Ideal for 2-3 couples or families, this pet-friendly property sleeps up to 8 guests across 3 bedrooms and 2 bathrooms, ensuring comfort and space for everyone.

Guest favourite

Cottage in Lusby

4.93 out of 5 average rating, 46 reviews

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.

Guest favourite

Cottage in Cambridge

4.96 out of 5 average rating, 166 reviews

Church Creek - waterfront cottage & pool - private

Close to Blackwater NWR and the Harriet Tubman Center, enjoy peaceful days at our secluded waterfront cottage on Church Creek. Our closest neighbor is across a cove. Our estate offers 50 acres of privacy and one of the best waterfront views on the Chesapeake. Enjoy a view from every window and nature all around you. Excellent walking, swimming (in-ground pool-May 3-Oct 1), great birding and bicycling. Launch your kayak from the backyard. Perfect private getaway!

Guest favourite

Cottage in Lusby

4.96 out of 5 average rating, 23 reviews

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.

Top guest favourite

Cottage in East New Market

4.96 out of 5 average rating, 71 reviews

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.