Compare best cottages in Maryland from 100+ sites!

About: This family-friendly cottage in St. Michaels is an excellent choice for travelers seeking a charming escape. It's just a short walk from the Chesapeake Bay Maritime Museum and other local attractions, and it has received excellent ratings for its location, cleanliness, and user experience.

The cottage has two bedrooms and can accommodate up to 5 guests. It features a fully equipped kitchen, a cozy fireplace, and a DVD player. Guests can also enjoy the outdoor space, which includes a terrace, a garden, and a swimming pool. The cottage also offers amenities such as air conditioning, Wi-Fi, and parking.

About: Cottage rental from $217 for up to 5 guests with an excellent rating of 100% based on 137 reviews. Your accommodation will be located in Bryans Road.

Facilities and services: a terrace, a kitchen and air conditioning. Enjoy free parking with this accommodation in Bryans Road!

About: Accommodation for up to 6 guests with an excellent rating of 98% based on 333 reviews. Your accommodation will be located in Deale.

Services and facilities include air conditioning, a washing machine and a freeze.

About: Cottage listing for up to 6 people with an excellent rating of 99% based on 94 reviews. You will be located in Prince Frederick.

Services and facilities include a garden, a fridge and free parking. This accommodation is ideal for families.

About: Cottage for 4 people with an excellent rating of 98% based on 122 reviews. This accommodation is based in Damascus.

Facilities and services include a washing machine, free parking and a fridge. This accommodation in Damascus also has air conditioning!

About: Cottage rental for up to 6 people with an excellent rating of 96% based on 10 reviews. You will be based in Chesapeake Beach.

Facilities and services include free parking, a barbecue and a fridge.

About: This waterfront cottage is situated in Pasadena on the Patapsco River, offering proximity to Lake Shore's cultural and recreational attractions. The cottage has received excellent user ratings and features one bedroom, one bathroom, and a guest capacity of four.

The cottage has a cozy interior with a galley kitchen, full bathroom, and upstairs loft with multiple beds. It also features a large porch for relaxation, air conditioning, a swimming pool, and a garden. The cottage is pet-friendly and offers access to a beach and fishing opportunities.

About: This waterfront cottage is nestled on an Eastern Shore Farm adjacent to Eastern Neck National Wildlife Refuge, an exclusive and private location. With excellent user, location, and cleanliness ratings, this cozy retreat offers a charming cottage ambiance with 2 bedrooms, 2 bathrooms, and a living area, accommodating up to 4 guests in 1190 square feet.

The cottage boasts unlimited access to 2 private docks for boating, kayaking, or paddleboarding, providing a serene waterfront experience. It also offers proximity to waterfront restaurants in Rock Hall and a nearby beach, providing easy access to dining and recreational options.

About: Cottage for up to 6 people with an excellent rating of 97% based on 35 reviews. You will be located in Port Deposit.

Facilities and services: a child space, a fridge and a freeze.

About: This waterfront cottage is located in North Beach, 2.5 miles from the Bayside History Museum and within 6 miles of Chesapeake Beach Water Park and Chesapeake Beach Railway Museum. It has excellent user ratings.

The cottage has 3 bedrooms, 2 bathrooms, and a floor area of 1100 square feet. It can accommodate up to 6 guests. It comes with a fully equipped kitchen, air conditioning, a swimming pool, a terrace or balcony, a garden, a spa, and parking. Guests have access to a water park, garden, and barbecue grills. Pets are allowed.

About: Enjoy a tranquil getaway at this charming cottage in Piney Point, surrounded by lush greenery and towering trees, with the soothing sounds of the Chesapeake Bay nearby. Just a stroll away from the serene shores, this highly-rated cottage offers a private deck with an outdoor grill, a spacious sunroom, and a fully equipped kitchen.

With one bedroom, one bathroom, and a guest capacity of two, the cottage boasts a floor area of 420 square feet. It features a queen-sized bed, a washer and dryer, air conditioning, and complimentary bicycles and seasonal kayaks for exploring the surrounding area.

About: This charming cottage in the quaint fishing village of Rock Hall, Maryland, offers a unique and memorable stay just steps away from a sandy beach and stunning sunset views over the Chesapeake Bay. The cottage has been recently renovated with a comfortable and inviting interior design, ensuring a relaxing stay for up to 5 guests.

The cottage features 2 bedrooms, 2 bathrooms, a well-equipped kitchen, air conditioning, a swimming pool, a terrace, a garden, a spa, and parking. It also offers excellent biking trails through the scenic countryside and is close to marinas, fishing charters, and crabbing opportunities.

About: The Little Red Oyster House is a waterfront cottage with a scenic location in the serene Abell district, only 6 miles from Leonardtown. It has excellent user ratings and offers direct access to St. Clements Bay for fishing, paddleboarding, and kayaking.

The cottage has three bedrooms and two bathrooms, and can accommodate up to six guests. It features a fully equipped kitchen, air conditioning, a terrace with a gas grill, a garden, and a spa. The master suite has waterfront views and an en suite bathroom.

About: Cottage with an excellent rating of 100% based on 367 reviews. You will be in Mayo.

Services and facilities include free parking, air conditioning and a dish washer. This accommodation in Mayo also has a garden!

About: Cottage rental from 398 dollars with an excellent rating of 98% based on 19 reviews. This accommodation is based in Riviera Beach.

Facilities and services: a dish washer, a washing machine and a barbecue. Take advantage of the Free Parking with this accommodation.

About: Cottage rental with an excellent rating of 96% based on 206 reviews. This accommodation is located in Easton.

Services and facilities: an iron, a kitchen and free parking. This accommodation in Easton has a swimming pool!

About: Cottage listing from 643 dollars for 6 guests with an excellent rating of 100% based on 48 reviews. You will be based in Arnold.

Facilities and services: air conditioning, a barbecue and a washing machine. Take advantage of the terrace in this accommodation!

About: This cottage is located in Cambridge, Maryland on the waterfront of Brooks Creek and Choptank River, within easy driving distance of Cambridge, Easton, St. Michaels, Salisbury, and Ocean City. It has excellent user ratings.

The cottage has 4 bedrooms, 2 bathrooms, and a floor area of 1870 square feet. It can accommodate up to 8 guests. The cottage has a fully equipped kitchen, a dining area, and a living room with comfortable seating. It also has a terrace/balcony, a garden, a tennis court, a swimming pool, and a Jacuzzi. Guests can enjoy water activities such as kayaking, fishing, and boating.

About: This cottage in St. Michaels offers a unique location within easy walking distance of major tourist attractions such as St. Michaels Museum, Chesapeake Bay Maritime Museum, and St. Michaels Winery. With excellent user ratings, this cottage provides a cozy and comfortable stay for up to 5 guests in its 1400 square feet of floor area with 2 bedrooms and 3 bathrooms.

The cottage features a fully equipped kitchen, multiple bathrooms, a private patio with a TV, and access to a garden with barbecue grills. Other amenities include air conditioning, a swimming pool, a terrace or balcony, and parking, making it an ideal choice for travelers seeking a convenient and well-equipped accommodation in Easton.

About: This charming cottage is situated in a tranquil area just 0.1 miles from the scenic Patuxent River, offering waterfront views and easy access to outdoor recreation. Within a short driving distance of popular tourist attractions, this cottage has received excellent ratings for its location, cleanliness, and overall experience.

The cottage features a cozy fireplace, creating a warm and inviting ambiance. With a floor area of 300 square feet, it has one bedroom and one bathroom, accommodating up to two guests. It is equipped with essential amenities such as a coffee/tea maker, a TV, and a private garden for relaxation or al fresco dining.

About: This 3-bedroom, 1-bathroom cottage is located on a private beach in the Point Lookout neighborhood of Scotland, Maryland, just 8 miles from St. Mary's College and less than 2 hours from Washington, D.C., with excellent user ratings.

The cottage has a fully stocked kitchen, a screened-in porch, a deck, a garden, a parking lot, and air conditioning. It also has a Jacuzzi, a terrace, a balcony, and a private beach with direct access to the Chesapeake Bay. The cottage can accommodate up to 8 guests and has two kayaks and life jackets for guest use.

About: Cottage listing for 4 guests with an excellent rating of 100% based on 407 reviews. You will be in Easton.

Facilities and services: a garden, a washing machine and a kitchen. Enjoy free parking with this accommodation in Easton!

About: Cottage rental for up to 5 people with an excellent rating of 99% based on 258 reviews. You will be located in North Beach.

Facilities and services include an iron, free parking and a dish washer.

About: Located in Rock Hall, Maryland, this updated cottage boasts stunning Chesapeake Bay views from its front porch and screened back deck, situated just 0.5 miles from the Rock Hall town beach and pool. With excellent user, location, and cleanliness ratings, this pet-friendly cottage offers a cozy and authentic experience in a quaint fishing village.

The cottage features two bedrooms, a sleeping porch with a pull-out sofa, and a comfortable living area, accommodating up to six guests in its 1000 square feet of floor space. Modern amenities include a 30-foot flat-panel TV, DVD player, Amazon FireTV, and Wi-Fi, while the screened back deck and front porch are ideal for enjoying sunsets over the bay. Guests can also enjoy the convenience of private parking and back door entry, as well as the proximity to local restaurants and attractions.

About: This waterfront cottage in West Annapolis provides easy access to the city's attractions and amenities, including the US Naval Academy and Annapolis City Dock (both 1.5 miles away). With excellent user, location, and cleanliness ratings, this cottage is a great choice for travelers looking for a comfortable and convenient stay in Annapolis.

The cottage has a floor area of 700 square feet and can accommodate up to 4 guests. It features a fully equipped kitchen, a comfortable queen bed, and a queen sofabed. The outdoor amenities include a fire pit, picnic area, kayaks, paddle boards, and a canoe.

About: Accommodation with an excellent rating of 97% based on 87 reviews. You will stay in Piney Point.

Services and facilities include a washing machine, a barbecue and a fridge. This accommodation in Piney Point also has air conditioning!

About: This waterfront cottage on Terrapin Sand Point is only 0.1 miles from the point and 2.5 miles from Smith Island. It is highly rated for its location, cleanliness, and user experience.

The cottage has 3 bedrooms and can accommodate up to 6 guests. It features a kitchen with a refrigerator, oven, stovetop, and microwave, as well as free WiFi, air conditioning, and a terrace or balcony. Guests can also enjoy the barbecue grills and garden.

About: Cottage with an excellent rating of 100% based on 61 reviews. You will be in Dunkirk.

Facilities and services: a barbecue, an iron and a kitchen. Take advantage of the Spa in this accommodation!

About: 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.

About: This cottage in Calvert Beach is located in a tranquil rural area near the beach in Port Republic, with frequent deer sightings and overhead wildlife. The cottage has an excellent user rating.

The cottage has 3 bedrooms, 2 bathrooms and a guest capacity of 10. It features a kitchen with a fridge, microwave oven, and dishwasher, air conditioning, a Jacuzzi, a garden, parking, and internet. Guests can enjoy wildlife observation, recreation, and access to family-friendly attractions.

About: This Chesapeake Beach cottage is a popular choice for families and pet owners due to its spacious floor plan, outdoor amenities, and convenient location near the beach and attractions. It has received very good user and location ratings, and an excellent cleanliness rating.

The cottage features two bedrooms, one bathroom, and a sofa bed, accommodating up to six guests in 960 square feet of space. It includes a fully equipped kitchen, a private deck for grilling and outdoor relaxation, and access to a community pool. Guests can also enjoy the cottage's jacuzzi, terrace, garden, and barbecue grills.

About: This charming cottage in Arnold's tranquil Cape Saint Claire district offers a relaxing getaway just 3.1 miles from Sandy Point State Park. With excellent user ratings, this cozy abode provides a comfortable stay for up to 5 guests.

The cottage features a spacious 660 square feet layout with one bedroom and one bathroom. Amenities include a fully equipped kitchen, air conditioning, a Jacuzzi, and a private terrace or balcony. Guests can enjoy complimentary breakfast, barbecue grills, and a garden for outdoor relaxation.

About: This Annapolis waterfront cottage is located on Bembe Beach in Eastport, offering panoramic Chesapeake Bay views and proximity to downtown Annapolis (4 miles) and the U.S. Naval Academy (4.5 miles). It has excellent user ratings.

The cottage has 3 bedrooms, 2 bathrooms, and can accommodate up to 8 guests. It features a gourmet kitchen, high-speed internet, a big flatscreen TV, luxury linens, and complimentary toiletries. Guests can enjoy a private beach, waterfront views, a spacious family suite, outdoor living areas, water activities, and luxury amenities.

About: Cottage from $280 for up to 6 guests with an excellent rating of 100% based on 5 reviews. You will be in Tilghman Island.

Facilities and services: a fridge, a child space and free parking.

About: This waterfront cottage in Cambridge, Maryland offers a unique and tranquil getaway for travelers visiting Madison. The cottage is situated in a rural area, providing guests with stunning views, private dock access, and proximity to the Blackwater National Wildlife Refuge.

The cottage features two bedrooms and one bathroom, accommodating up to six guests. The fully equipped kitchen, laundry room, and comfortable living and sleeping areas ensure a comfortable stay. Guests can enjoy amenities such as air conditioning, a Jacuzzi, a garden, and parking.

About: Oyster Cottage is a pet-friendly cottage in Rock Hall, MD, just steps away from shopping, dining, and the waterfront. It has an excellent user rating and can accommodate up to 7 guests.

The cottage has two living room spaces, a well-equipped kitchen, an outdoor living space with a grill, and a unique side garden. It also has air conditioning, a Jacuzzi, a terrace/balcony, a garden, parking, and internet access.