Compare best cottages in Maryland from 100+ sites!

This Piney Point cottage is a short drive from Point Lookout State Park, Elms Beach Park, and Confederate Memorial Park, offering easy access to the area's natural beauty and historical sites. It has received excellent user ratings, indicating a comfortable and enjoyable stay for guests.
The two-bedroom cottage spans 980 square feet and comfortably accommodates up to eight guests. Enjoy amenities like a fully equipped kitchen, air conditioning, a terrace, a garden, and free Wi-Fi, perfect for relaxing and enjoying the beautiful surroundings.

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 charming beach house is just 9 miles from Severna Park, offering easy access to attractions like the B&A Trail, Severna Park Golf Center, and Bay Hills Golf Club. The property consistently receives excellent ratings for location, cleanliness, and overall user experience.
The 560 square foot cottage comfortably accommodates two guests in one bedroom and one bathroom. Enjoy the private garden, relax on the balcony, or unwind in the arcade/game room, all while having access to a fully equipped kitchen, free WiFi, and a charcoal grill for outdoor dining.

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 Rock Point cottage rental, located in Chaptico, Maryland, is conveniently situated within a 9-mile radius of attractions like Country Lakes Community Park, Maryland International Raceway, and Budds Creek Motocross Track.
This two-bedroom, one-bathroom vacation home sleeps six guests and boasts a fully equipped kitchen, patio with grill, smart TV, and concierge service, offering a comfortable and family-friendly stay.

This charming cottage is located in St. Michaels, a short walk from the Chesapeake Bay Maritime Museum and other popular attractions. It has consistently received excellent ratings for its location, cleanliness, and overall experience.
The two-bedroom cottage provides 1400 square feet of space for up to five guests. Enjoy a relaxing stay with amenities like a private garden, a swimming pool, and a spa, as well as a fully equipped kitchen and modern conveniences like air conditioning and Wi-Fi.

This Cambridge, MA cottage, 4.5 miles from Ragged Island and 12 miles from Spocott Windmill and several maritime museums, offers convenient access to Madison's attractions.
This three-bedroom, two-bathroom house sleeps six, includes a washer, sofa bed, and amenities like a hairdryer and iron, ensuring a comfortable stay near Cambridge's local amenities.

This Colesville cottage, near Silver Spring, MD, is conveniently located under 6 miles from Brookside Gardens, Olney Theatre Center, and the Patuxent River.
This pet-friendly vacation home features two bathrooms, a fully equipped kitchen with a microwave, free Wi-Fi in public areas, free self-parking, a private patio, and air conditioning.

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, 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.

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 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 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 charming cottage is located in Port Deposit, just a short drive from Hollywood Casino, Garrett Island Beach, and Perry Point VA Medical Center. The cottage boasts excellent user, location, and cleanliness ratings, making it a popular choice for travelers.
This cozy vacation home is 1910 square feet and has three bedrooms and one bathroom. Guests can enjoy a private fenced yard, a fireplace, a fitness center, a spa tub, and a fully equipped kitchen with a refrigerator, oven, microwave, and dishwasher.

This Anne Arundel County cottage is a short drive from Annapolis and Washington, D.C., offering easy access to regional attractions and is located 6 miles from South River Golf Links.
This rental sleeps four guests with one bedroom, a double bed, and a sofa bed, and includes air conditioning and internet for a comfortable stay.

Simplicity Cottage is located on Tilghman Island, a short drive from the Smithsonian Environmental Research Center and Matapeake State Park, offering a peaceful escape on the Chesapeake Bay. The cottage provides a comfortable stay for up to four guests with two bedrooms and two bathrooms. This waterfront home has a private dock for fishing or kayaking, a spacious yard for outdoor activities, and is close to local attractions, making it a perfect base for exploring the island.