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This charming cottage sits on the Chesapeake Bay in Piney Point, offering a private beach and fishing pier, just a short walk from a semi-public beach and close to local attractions. The property has consistently received excellent ratings for its location, cleanliness, and overall experience.
The cottage has three bedrooms and two bathrooms, comfortably accommodating up to eight guests. Enjoy a relaxing stay with amenities like a fully equipped kitchen, air conditioning, a terrace, and a garden, as well as access to water activities such as kayaking, paddleboarding, and fishing.

This Piney Point waterfront cottage, located in Point Lookout, Southern Maryland, offers stunning Chesapeake Bay views and is minutes from Point Lookout State Park and the Smith Island Ferry.
The 1020-square-foot home features two bedrooms, one bathroom, sleeps six, and includes a fully equipped kitchen, high-speed Wi-Fi, air conditioning, a private dock, fire pit, and Adirondack chairs.

This charming cottage is located just a short drive from the Susquehanna River and offers easy access to nearby attractions like Elk Neck State Park. It's received very good ratings from previous guests.
The cottage has one bedroom and one bathroom, with a total floor area of 1500 square feet, comfortably accommodating up to four guests. The cottage offers amenities like air conditioning, a kitchen with a fridge and microwave, Wi-Fi, a garden, and a smart TV, making it a perfect choice for a relaxing getaway.

This Charlestown cottage is located on Cattail Creek, just steps from the sandy beach at Footlog Park and a short drive from Havre de Grace.
The two-bedroom, one-bathroom cottage features a private dock, kayaks, and stunning waterviews from most areas, perfect for a relaxing getaway for up to four guests.

This pet-friendly Garrison cottage, located in Owings Mills, Maryland, is 2.4 miles from Foundry Row, within 6 miles of Stevenson University and Greenspring Station, and within 9 miles of Johns Hopkins Health Care & Surgery Center and the Under Armour Performance Center Baltimore Ravens.
This 4.5-bathroom vacation home features a fully equipped kitchen with microwave and dishwasher, an outdoor patio, BBQ facilities, and free Wi-Fi in public areas; it offers convenient access to nearby attractions.

This Chance waterfront home is located 1.6 miles from Shark Fin Shoal and 2.4 miles from Rock Island, with easy access to the Whitehaven Historic District and Mount Vernon Park within 20 miles.
This 2160-square-foot vacation rental boasts four bedrooms, two bathrooms, and accommodates up to nine guests, featuring a fully equipped kitchen, laundry facilities, patio, and charcoal grills; pets are welcome.

This cottage in Darnestown offers an exclusive farm setting, providing a peaceful retreat approximately 25-40 minutes from Washington D.C. and Baltimore, with convenient access to Seneca Creek State Park, Sugarloaf Mountain, and Black Hill Regional Park. This accommodation features 3 bedrooms, 2 bathrooms, and a capacity for 6 guests, with amenities including air conditioning, a kitchen with a fridge, microwave, and dishwasher, a swimming pool, garden, and tennis court, plus optional on-site horse boarding and unique farm experiences.

This two-bedroom cottage in Piney Point is located near the Piney Point Lighthouse and Cecil's Old Mill, with St. Mary's River State Park and Salem State Forest also nearby.
This family-friendly rental accommodates up to five guests and includes a kitchen with a fridge and microwave, air conditioning, and internet access, plus full access to a private, fenced beach at 16431 Thomas Road, St. George Island Beach for fishing, crabbing, and picnicking.

This beachfront cottage in Piney Point offers direct access to the Chesapeake Bay, ideal for crabbing, fishing, and enjoying the water.
Accommodating up to 12 guests, this 5-bedroom, 3-bathroom residence features a gourmet kitchen, hot tub with bay views, screened porch, private deck, kayaks, a stand-up paddleboard, and a Tesla charger.

This 4-bedroom cottage in Ballenger Creek is the perfect place to relax and unwind. Situated on 5 acres of private land, it offers a peaceful retreat from the hustle and bustle of city life. Despite its secluded setting, the cottage is conveniently located near major highways, making it easy to explore the surrounding area.
With a user rating of "excellent," this cottage is a popular choice for travelers visiting Ballenger Creek. It features a private pool, heated spa, and gourmet kitchen, providing guests with the ultimate in comfort and relaxation. The cottage also has four bedrooms, one bathroom, and can accommodate up to 8 guests. Guests can enjoy hiking, biking, or simply relaxing amidst the beautiful natural surroundings.

This charming cottage is located in the peaceful neighborhood of Cape Saint Claire, just 3.1 miles from Sandy Point State Park and within 6 miles of both Sandy Point Beach and Bay Hills Golf Club. Guests consistently rate this cottage as excellent, making it a popular choice for travelers seeking a comfortable and convenient stay.
The cottage offers 660 square feet of space, accommodating up to 5 guests in a single bedroom and bathroom. Enjoy modern conveniences like air conditioning, a Jacuzzi, a terrace, a garden, and a spa, as well as a fully equipped kitchen and free Wi-Fi.

This St. Leonard beach house offers proximity to three private beaches within walking distance or a short drive, and is 15 miles from Solomons Island and Prince Frederick.
This family-friendly cottage accommodates four guests with two bedrooms and one bathroom, featuring a full kitchen, air conditioning, a jacuzzi, a garden, parking, and shared amenities like a fire pit and kayaks.

This Port Deposit vacation home is located 0.4 miles from the Susquehanna River, within 6 miles of Hollywood Casino and Garrett Island Beach, and under 9 miles from Perry Point VA Medical Center and Conowingo Dam.
This three-bedroom, one-bathroom house sleeps nine guests and features a fully equipped kitchen, a swimming pool, a terrace, free Wi-Fi, and a Smart TV; an on-site water park provides additional recreation.

This Piney Point cottage, near Point Lookout State Park (1 mile), Buzz's and Drury's marinas (4 miles), and Piney Point Lighthouse (27 miles), offers a convenient location for exploring the Chesapeake Bay area. This 420-square-foot vacation home features one bedroom, one bathroom, sleeps three guests, includes a full kitchen, washer/dryer, and a sunroom, plus a furnished deck with a charcoal grill; one pet is allowed for a fee.

This Wittman cottage is located approximately 15-16 minutes by car from St. Michaels Marina, the Chesapeake Bay Maritime Museum, Perry Cabin Park, and Back Creek Park, offering convenient access to maritime attractions and recreational areas. This 2-bedroom, 1-bathroom rental accommodates up to 4 guests and includes amenities such as air conditioning and Wi-Fi, with pets welcome.

This Westover cottage offers prime waterfront living on the Big Annemessex River, located 11 miles from the University of Maryland Eastern Shore and Janes Island State Park.
This pet-friendly vacation home spans 1150 square feet, accommodating up to 7 guests in 2 bedrooms and a loft, and features direct river access with provided equipment for water activities.