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

Top guest favourite

Cottage in Westover

4.99 out of 5 average rating, 228 reviews

Rumbley Cottage on the Tangier Sound-Private Beach

LAST MINUTE AVAILABILITY - JULY 19-25 FOUR NIGHT MINIMUM STAY 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 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.

Guest favourite

Cottage in Scotland

4.9 out of 5 average rating, 31 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.

Top guest favourite

Cottage in Oxford

5 out of 5 average rating, 21 reviews

Sailor's Cottage - Private Waterfront

Sailor's Cottage lets you get away from it all within walking distance of the charming and historic town of Oxford. This idyllic retreat on 29 acres is the perfect private hideaway for family and friends to enjoy the best of Eastern Shore living. The craftsman-built home is inviting and inspiring. Relax with your morning coffee on the screened-in porch, have cocktails on the dock, or take a paddle on protected Boone Creek. Longer stays are encouraged to take advantage of all there is to do.

Top guest favourite

Cottage in Woolford

5 out of 5 average rating, 68 reviews

Waterfront Cottage 3BR 2 BA, Pier, Sunsets,Kayaks

Just 15 minutes from Cambridge on the Eastern Shore you get a waterfront Cottage plus a bonus Guesthouse. Total 3 bedrooms 2 baths. Head to Oxford, St. Michaels and Easton for day trips. Watch beautiful sunsets, kayak or paddle board. Relax on the deck, fish and crab directly off the pier. There’s a a hot tub, gas grill and fire pit. The cottage and guest house accommodates up to 8 people. This property is great for 2-3 couples or families that need a place with more than one bathroom.

Guest favourite

Cottage in Westover

4.92 out of 5 average rating, 53 reviews

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).

Superhost

Cottage in Westover

5 out of 5 average rating, 3 reviews

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!

Superhost

Cottage in Deal Island

4.64 out of 5 average rating, 238 reviews

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!

Top guest favourite

Cottage in Princess Anne

5 out of 5 average rating, 15 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!

Guest favourite

Cottage in Cambridge

4.96 out of 5 average rating, 154 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!

Top guest favourite

Cottage in East New Market

4.95 out of 5 average rating, 65 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.