Compare best cottages in Maryland from 100+ sites!

This Benedict, Maryland beach house boasts a unique beachfront location with over 500 feet of private beach and a 400-foot pier, near the Dr. Samuel A. Mudd House Museum and Drum Point Lighthouse.
This one-bedroom, one-bathroom vacation rental sleeps six, featuring a queen bed, bunk beds, a sleeper sofa, a full kitchen with a fridge and microwave, air conditioning, a terrace, a garden, a spa, and a gas grill; enjoy nearby Walter's Walk sandbar for sunset viewing.

This 800-square-foot cottage rental near Hydes, Baltimore County, provides easy access to Oregon Ridge Nature Center, Ladew Topiary Gardens, and wineries.
The one-bedroom, one-bathroom house sleeps three, features a full kitchen with a refrigerator and microwave, air conditioning, and a private garden; well-behaved dogs are allowed with prior approval.

This Centreville cottage, located 0.9 miles from the Hazel Miner Monument and within a 9-mile radius of attractions like Cassinelli Winery & Vineyards and Wye Oak State Park, offers a convenient base for exploring the area. This one-bedroom, one-bathroom home sleeps four and features a fully equipped kitchen, air conditioning, a terrace, a garden, and parking, plus on-site barbecue grills for outdoor relaxation.

This Williamsport cottage, located in the city center near the Potomac River, offers easy access to Hagerstown Suns Municipal Stadium and Antietam National Battlefield.
The 1190-square-foot three-bedroom house sleeps six, featuring a fully equipped kitchen, two bathrooms, three smart TVs, WiFi, a washer/dryer, and a private garden; nearby recreational activities include birdwatching and hiking.

This three-bedroom, three-bathroom vacation home in Worton, Maryland, near Still Pond Creek, is two miles from the Old Coast Guard Station beach and Betterton Historic District.
The 1910-square-foot house features a private beach access with kayak and bike rentals, a well-equipped kitchen, and multiple indoor/outdoor relaxation areas, accommodating up to six guests.

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 cottage is located in the downtown St. Michaels city center, offering immediate walkability to shops, dining, the St. Michaels Museum, and the Classic Motor Museum, situated on a quiet street for a peaceful getaway. This 900 square foot rental accommodates two guests with one bedroom and one bathroom, featuring air conditioning, a full kitchen with a fridge, microwave, and dishwasher, a private fenced backyard, an enclosed front porch, and is near opportunities for jet skiing, kayaking, and motor boating.

This Piney Point waterfront cottage offers two bedrooms, one bathroom, and sleeps six, providing easy access to the Piney Point Lighthouse and Patuxent River Naval Air Museum.
The fully equipped kitchen includes a refrigerator, microwave, stove, and cooktop; amenities include air conditioning, Wi-Fi, laundry facilities, and a BBQ grill, plus smart TVs in each bedroom.

Hays Beach House is a waterfront cottage situated in the Point Lookout neighborhood of Scotland, Maryland, near Historic St. Mary's City and Patuxent River Naval Air Museum. It has an excellent user rating.
The cottage has 5 bedrooms and 5 bathrooms, and can accommodate up to 12 guests. It features a private beach with crabbing, fishing, kayaking, and stand-up paddleboarding opportunities, a hot tub on the screened porch with sunset views, a private deck overlooking the bay, a gourmet kitchen, a balcony on the top floor with panoramic Chesapeake Bay vistas, and is pet-friendly.

This Long Beach, St. Leonard's cottage offers easy beach access, a short walk from Flag Ponds Nature Park and Flag Harbor Marina, and less than 1.2 miles from Long Beach and Matoaka Beach.
This 800-square-foot vacation home sleeps five, boasting two bedrooms, two bathrooms, a full kitchen, a private patio, plus on-site amenities including a swimming pool, hot tub, and barbecue grills.

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 Long Beach vacation home, located in Saint Leonard, Maryland, is a short drive from Solomons Island and Prince Frederick, offering easy access to three private beaches (with provided parking passes for two).
The two-bedroom, one-bathroom house sleeps four, features a fully equipped kitchen with a dishwasher and Fiestaware, a Jacuzzi, and access to shared kayaks, paddleboards, and a fire pit; two 43-inch smart TVs and a 55-inch smart TV are also available.

This Stevensville, Maryland coastal cottage, a short drive from Annapolis and easily accessible to Kent Island wedding venues, offers convenient proximity to Queenstown Harbor Golf Links and Paul Reed Smith Guitars.
This 1190-square-foot vacation home features two bedrooms, two bathrooms, and accommodates six guests, boasting a screened porch with fireplace, a private barrel sauna, and outdoor amenities including a BBQ grill and firepit.

This waterfront cottage on Cobb Island offers river views and is a 0.3-mile walk to the water taxi for St. Clements Island State Park, with Coltons Point Marina 2 miles away and Leonardtown 15 miles distant.
This 800 square foot, 2-bedroom, 1-bathroom rental accommodates up to 4 guests and features a private pier for fishing and crabbing, a water-view balcony, step-free entry, and a kitchenette.

This Queenstown, Maryland cottage is conveniently located near the Avalon Theatre and The Third Haven Friends Meeting House, offering easy access to area attractions like the Hazel Miner Monument and Adkins Arboretum.
This two-bedroom, one-bathroom house sleeps four guests and features a fully equipped kitchen (fridge, microwave), air conditioning, Wi-Fi, a terrace, garden, parking, and a washer/dryer; pets are welcome.

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.