Search All Cottages in Chesapeake Bay

This cottage, a cosy tiny house, is located in Piney Point, a short distance from the historic Piney Point Lighthouse and Cecil's Old Mill, and close to St. Mary's River State Park.
This accommodation sleeps up to five guests across two bedrooms and offers internet, air conditioning, a kitchen with a fridge and microwave, and exclusive access to a private sandy beach for fishing, crabbing, and picnicking.

This waterfront property is situated just a short drive from Cambridge, Maryland, offering easy access to nearby towns like Easton, St. Michaels, Salisbury, and Ocean City. The cottage enjoys an excellent user rating, reflecting its high standards and appeal to travellers.
This four-bedroom, two-bathroom home spans 174 square metres and comfortably accommodates up to eight guests. The property offers a range of amenities, including a swimming pool, jacuzzi, tennis court, and a fully equipped kitchen, perfect for families and groups seeking a relaxing and enjoyable stay.

Simplicity Cottage is situated on Tilghman Island, a short distance from the Tilghman Watermen’s Museum and Chesapeake Bay Maritime Museum, offering a peaceful retreat surrounded by the scenic Chesapeake Bay. This charming holiday home is perfect for a small family or group of friends seeking a relaxing getaway.
The cottage has two bedrooms and two bathrooms, comfortably accommodating up to four guests. It features a waterfront location with a substantial dock, air conditioning, internet access, and a spacious lot perfect for outdoor activities and entertaining.

This waterfront holiday home in Hague, Northern Neck, Virginia, is situated close to the Kinsale Museum and Piney Point Lighthouse, offering easy access to local wineries.
The two-bedroom, two-bathroom property sleeps seven, boasts a fully equipped kitchen, private 50ft dock, and spectacular Potomac River views, perfect for fishing, crabbing, or simply enjoying the scenery.

This waterfront cottage is situated in White Stone, Virginia, just a short drive from award-winning restaurants and a marina. The cottage has consistently received excellent reviews for its location, cleanliness, and overall experience.
The cottage spans 126 square metres and comfortably accommodates up to six guests in its three bedrooms and two bathrooms. Enjoy stunning views of the bay and creek from the porch swings, take advantage of the high-speed internet, and explore the area by kayak, launching from the floating dock or nearby community boat ramp.

This charming cottage is located just a short distance from the Steamboat Era Museum and Historic Christ Church, offering a tranquil escape from the hustle and bustle of the city. Guests consistently rate this property as excellent, highlighting its peaceful setting and comfortable amenities.
The cottage provides spacious accommodation for up to four guests, with two bedrooms and two bathrooms spread across 158 square metres. Guests can enjoy a range of amenities, including a fully equipped kitchen, a private garden, a spa, a tennis court, and a barbecue grill, making it ideal for families or groups seeking a relaxing retreat.

This detached house is located in Princess Anne, offering convenient access to Cedar Hill Marina and Bordeleau Winery, with Mount Vernon Park and Mount Vernon Beach a short distance away.
This property accommodates up to six guests across two bedrooms and one bathroom, featuring a fully equipped kitchen, a grill, complimentary WiFi, parking, and an expansive deck overlooking the Wicomico River, with an optional boat slip available for an additional charge.

This family-friendly holiday home is located in Virginia Beach, just a mile from First Landing State Park and Marina Shores Marina, with Chesapeake Beach and Sylvan Beach within a three-mile radius. It has received excellent reviews from previous guests.
The cottage has three bedrooms and three bathrooms, providing ample space for up to six guests. It features a fully equipped kitchen, a private swimming pool, a terrace, a garden, and a spa, ensuring a comfortable and enjoyable stay.

This waterfront holiday home in Woolford, near Cambridge and the Blackwater National Wildlife Refuge, offers proximity to the Harriet Tubman Underground Railroad National Historical Park.
This 149 square meter holiday home accommodates up to 8 guests across a 2-bedroom main house and a 1-bedroom guesthouse, featuring direct access to crabbing and fishing with a pier, provided kayaks, a hot tub, and a fire pit for year-round comfort.

This family-friendly beach lodge in St. Leonard, Maryland, offers access to three private community beaches and is situated within 160 kilometres of Washington D.C. and Joint Base Andrews, 72 kilometres from Waldorf, and 24 kilometres from Solomons Island.
This two-bedroom holiday home accommodates up to four guests, featuring two smart TVs, a bathroom with a tub, a living area with a pellet stove, a fully equipped kitchen, and on-site laundry facilities, with shared amenities including a fire pit and kayaks for exploring the bay.

This Cheriton cottage, situated 13km from Cape Charles' historic district and beaches, provides easy access to Bay Creek Resort (14km) and Kiptopeke State Park (19km).
The 37 square metre self-catering property sleeps four, boasting two bedrooms, one bathroom, a Jacuzzi, a terrace, a garden, parking, and a well-equipped kitchen including a dishwasher and a Keurig coffee machine, plus on-site hot tub and gas grill.

This charming cottage is located in Cape Saint Claire, just a short drive from Arnold's attractions, including Sandy Point State Park and Sandy Point Beach. The cottage has received excellent user ratings, making it a popular choice for travellers.
This holiday home offers 61 square metres of space, comfortably accommodating up to 5 guests in its one bedroom and one bathroom. The cottage is equipped with a range of amenities, including a fully fitted kitchen, a spa, a terrace, a garden, parking and Wi-Fi, ensuring a comfortable and enjoyable stay.

This Lee Mont waterfront holiday home is situated near Parksley, approximately 10km from Parksley Town Park and the Eastern Shore Railway Museum, and 14km from Bloxom Winery and the Accomac Historic District.
The 74 square metre property offers one bedroom, one bathroom, sleeps four guests, and includes a fully equipped kitchen, Wi-Fi, patio, garden, parking, and air conditioning.

This waterfront holiday home in Kilmarnock offers a private 30-meter pier and a small sandy beach, located a short drive from the Steamboat Era Museum and the Mary Ball Washington Museum and Library.
This spacious 134 square meter cottage accommodates up to six guests across four bedrooms and two bathrooms, featuring a microwave, dishwasher, air conditioning, a terrace, garden, and parking, with complimentary use of SUPs for exploring the shoreline.

This Wittman holiday home offers a convenient base on Tilghman Island, located within a 2.4 to 2.6 kilometre drive of Perry Cabin Park, Back Creek Park, St. Michaels Marina, and the Chesapeake Bay Maritime Museum, with Wittman Park and CL Open Field also easily accessible for nature enthusiasts.
This two-bedroom property accommodates up to four guests, providing essential amenities including Wi-Fi, air conditioning, a dryer, and towels, and is a short drive from cultural sites like the Tilghman Watermen’s Museum and outdoor recreational areas such as Phillips Wharf Environmental Center.

This waterfront holiday home in Painter, Virginia, is located half a block from a private neighbourhood beach and offers proximity to the Eastern Shore Yacht and Country Club Golf Course and Port Of Wachapreague Town Marina.
This 135 square metre cottage offers accommodation for up to six guests, featuring three bedrooms, one bathroom, a fully equipped chef's kitchen, a sunroom with a pull-out bed, and complimentary kayaks, paddleboards, and bicycles for enjoying the bay and ocean.