Cottages in Maryland

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Maryland cottages
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1577 Best cottages in Maryland

Best family friendly Maryland cottages

Among the 1577 accommodations in Maryland, here are the 4 best family friendly cottages

Comfortable Cottage In Gated Community, 5 Mins To Oc And Assateague - Maryland
9.8 53 reviews

Comfortable Cottage In Gated Community, 5 Mins To Oc And Assateague

cottage, West Ocean City
This West Ocean City holiday home is situated in the Assateague Pointe community of Berlin, Maryland, a short distance (a few kilometres) from Ocean City Inlet, Assateague Island, and Frontier Town water park.
The 69 square metre self-catering property sleeps six adults across two bedrooms and one bathroom, boasting a private patio, community swimming pool, tennis court, and access to a catch-and-release pond with paddle boats.
Secluded Waterfront:kayaks, Sunrises & Unwind - Maryland
9.8 77 reviews

Secluded Waterfront:kayaks, Sunrises & Unwind

cottage, Piney Point
This three-bedroom waterfront holiday home in Ridge, Maryland, is situated approximately 13km from Point Lookout State Park, a significant historical site.
Sleeping up to ten guests, the property boasts a spacious open-plan layout, a fully equipped kitchen including a dishwasher, high-speed Starlink WiFi, on-site kayaks and paddleboards, and a Tesla charger, plus blackout curtains and welcome snacks.
Private Beach Front Getaway At The Sunshine Beach Cottage. - Maryland
9.8 87 reviews

Private Beach Front Getaway At The Sunshine Beach Cottage.

cottage, Piney Point
This charming beach house is situated just 8 kilometres from Point Lookout State Park and within a 19 kilometre radius of several other attractions, offering easy access to the region's natural beauty and historical sites. It has received excellent user ratings, making it a popular choice for families and groups.
The two-bedroom property spans 91 square metres and comfortably accommodates up to 8 guests. The cottage features a range of amenities, including a fully equipped kitchen, a cosy fireplace, a terrace, and a garden, ensuring a relaxing and enjoyable stay.
Beautiful Waterfront 2-bedroom Cottage In Tranquil Piney Point With Wifi, Ac - Maryland
10 7 reviews

Beautiful Waterfront 2-bedroom Cottage In Tranquil Piney Point With Wifi, Ac

cottage, Piney Point
This Piney Point waterfront holiday home is situated near St Mary's River State Park and the Piney Point Lighthouse, offering tranquil river views.
Sleeping up to six guests, the two-bedroom property boasts a fully equipped kitchen, air conditioning, Wi-Fi, smart TVs, and on-site barbecue facilities, making it ideal for families exploring the local area's attractions including the Patuxent River Naval Air Museum.

Top cities

Best Maryland cottages with a garden

𝑩𝑨𝒀 𝑺𝑰𝑫𝑬 𝑹𝑬𝑻𝑹𝑬𝑨𝑻, On The Sands Of The 𝐂𝐇𝐄𝐒𝐀𝐏𝐄𝐀𝐊𝐄 𝐁𝐀𝐘 - Maryland
10 137 reviews

𝑩𝑨𝒀 𝑺𝑰𝑫𝑬 𝑹𝑬𝑻𝑹𝑬𝑨𝑻, On The Sands Of The 𝐂𝐇𝐄𝐒𝐀𝐏𝐄𝐀𝐊𝐄 𝐁𝐀𝐘

cottage, Piney Point
This charming cottage is situated in Point Lookout, a peaceful neighbourhood in Scotland, Maryland, just 13km from St. Mary’s College and less than 3 hours from Washington D.C. It has received excellent reviews from previous guests, making it a popular choice for travellers seeking a relaxing getaway.
The cottage offers three bedrooms and sleeps up to eight guests comfortably. It features modern amenities such as a fully equipped kitchen, a private beach, a screened-in porch, kayaks, fishing poles, and a Jacuzzi, ensuring a memorable stay.
Private Beach And Inviting Hot Tub - Charming Coastal Oasis - Maryland
9.6 29 reviews

Private Beach And Inviting Hot Tub - Charming Coastal Oasis

cottage, Piney Point
This spacious five-bedroom, three-bathroom holiday home in Piney Point offers direct access to a private beach on the Chesapeake Bay and features a gourmet kitchen, air conditioning, and a hot tub with bay views.
Guests can enjoy provided kayaks and paddleboards, a private deck, a top-floor balcony with expansive bay vistas, and a Tesla charging station, with accommodation for up to twelve people and pet-friendly options available.
Luxurious 4br, Private Pool, Heated Spa-open Year-round, Near Downtown! - Maryland
10 159 reviews

Luxurious 4br, Private Pool, Heated Spa-open Year-round, Near Downtown!

cottage, Ballenger Creek
This charming cottage is located in Ballenger Creek, just 10 kilometres from the historic centre of Frederick, offering a peaceful retreat in a quiet, secluded area. It has received excellent user ratings, reflecting its high standard of comfort and service.
The cottage spans 186 square metres and comfortably accommodates up to eight guests, with four bedrooms and a bathroom. It offers a range of amenities, including a swimming pool, a spa, a terrace, a garden, and a gourmet kitchen, providing everything you need for a relaxing and enjoyable stay.
Waterfront Cottage In Historic Charlestown, Maryland - Maryland
10 11 reviews

Waterfront Cottage In Historic Charlestown, Maryland

cottage, Charlestown
This Charlestown cottage is situated on the bend of Cattail Creek, just a short walk from the sandy beach at Footlog Park and within easy reach of the Susquehanna Museum at the Lock House, Concord Point Lighthouse, and Mount Felix Vineyard & Winery. The two-bedroom property sleeps up to four guests and boasts a private dock, two kayaks, waterfront views, and a fully equipped kitchen with a fridge, microwave oven, and dishwasher.

Frequently asked questions about cottages in Maryland

  • What are the top must-see attractions in Maryland, United States?

    Maryland boasts a fantastic array of attractions. For history buffs, a visit to the Inner Harbour in Baltimore, with its maritime museum and historic ships, is a must. Fort McHenry, where the Star-Spangled Banner was inspired, offers stunning views and a significant piece of American history. Annapolis, the state capital, is charming, with its historic buildings and the United States Naval Academy. Nature lovers should explore Assateague Island National Seashore, famous for its wild horses, or the scenic beauty of the Chesapeake Bay.
  • What are the best cottages in Maryland?

  • How can one spend a 5-day holiday in Maryland, United States?

    A five-day trip allows for a good exploration of Maryland. Spend a day or two in Baltimore, visiting the Inner Harbour, Fort McHenry, and exploring the city's vibrant neighbourhoods. Then, head to Annapolis, exploring its historic district and the Naval Academy. Dedicate a day to the Eastern Shore, perhaps visiting Assateague Island National Seashore. The remaining day could be spent exploring the Chesapeake Bay region, perhaps with a boat trip or visiting a charming coastal town like St. Michaels.
  • What are the best cottages with a pool in Maryland?

  • Is Maryland, United States a good destination to rent a cottage?

    Absolutely! Maryland offers many opportunities for cottage rentals, particularly on the Eastern Shore and along the Chesapeake Bay. Ocean City, while known for its hotels, also has many charming cottages available. The quieter areas of the Eastern Shore provide a peaceful retreat, perfect for a cottage holiday.
  • What are the best cottages with a jacuzzi in Maryland?

  • What weather, wildlife, or natural hazards might affect travellers in Maryland, United States?

    Maryland experiences hot, humid summers and mild winters. Hurricanes are a possibility, particularly during late summer and autumn, mainly affecting the coastal areas. Be aware of the potential for severe thunderstorms, especially during the summer months. Wildlife encounters are possible, including deer, raccoons, and various bird species. Mosquitoes can be prevalent in the warmer months, so insect repellent is advisable.
  • What are the best cottages for families and kids in Maryland?

  • Is Maryland, United States pedestrian and cyclist-friendly?

    Maryland's pedestrian and cycling infrastructure varies. Cities like Annapolis and Baltimore have areas that are quite walkable, though some areas might require more caution. Dedicated cycling paths are available in some areas, particularly along the Chesapeake Bay and in some parks, but it's advisable to check local cycling maps before setting off on longer journeys.
  • What are the best pet friendly cottages in Maryland?

  • Are there any unusual or hidden places to explore in Maryland, United States?

    Yes! Explore the charming town of Ellicott City, with its historic mill and unique shops. The Catoctin Mountains offer scenic hiking trails and waterfalls, less crowded than some better-known parks. Assateague Island, while popular, still retains a sense of remoteness and offers opportunities for quiet exploration beyond the main areas.
  • What are the best cottages with parking in Maryland?

  • What are some of the best cultural experiences that allow one to meet locals in Maryland, United States?

    Attending local festivals is a great way to meet people. Many towns and cities hold regular farmers' markets, offering a chance to interact with local producers and residents. Visiting smaller, less touristy towns on the Eastern Shore allows for more authentic interactions with the local community. Participating in a local cooking class focusing on Maryland cuisine could also be a rewarding experience.
  • What are the best authentic dishes to taste in Maryland, United States?

    Maryland's cuisine is heavily influenced by its Chesapeake Bay location. Crab cakes are a must-try, but ensure they are made with plenty of lump crab meat. Chesapeake Bay blue crabs, steamed or in a crab soup, are another classic. Smith Island cake, a unique layered dessert, is a delicious treat. Try local oysters, known for their fresh flavour.

Nearby regions

Best Maryland cottages with a jacuzzi

Among the 1577 accommodations in Maryland, here are the 4 best cottages with a jacuzzi

Year Round Playground - Rare Rustic-modern Getaway - Maryland
No reviews

Year Round Playground - Rare Rustic-modern Getaway

cottage, Fairmount
This Fairmount holiday home is situated in Marion Station, Maryland, approximately 16km from Great Hope Golf Course and a supermarket, and around 160km from Ocean City and Assateague Island, near Crisfield and the Coventry Parish Ruins.
The four-bedroom, three-bathroom property sleeps eight guests and boasts a private pool (open Memorial Day to Labor Day), a seven-person hot tub, a fully equipped outdoor kitchen, a spacious recreation room with an 85-inch TV and pool table, and a unique waterfront location on East Creek with a private dock offering bay access.
Block To Beach! Fossil Hunting, Hot Tub, Coffee Bar, Screened Deck, 1hr To Dc - Maryland
10 22 reviews

Block To Beach! Fossil Hunting, Hot Tub, Coffee Bar, Screened Deck, 1hr To Dc

cottage, Long Beach
This St. Leonard's cottage, near Long Beach, offers easy access to Flag Ponds Nature Park and Flag Harbour Marina, both within 1.6km, and is less than 1.6km from Long Beach and Matoaka Beach.
This 74 square metre holiday home sleeps five, boasting two bedrooms, two bathrooms, a fully equipped kitchen, swimming pool, jacuzzi, and terrace, plus free Wi-Fi and on-site parking.
Waterfront Fishing Creek Cottage With Guesthouse Pier-kayaks-fire Pit - Maryland
No reviews

Waterfront Fishing Creek Cottage With Guesthouse Pier-kayaks-fire Pit

cottage, Madison
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.
Cottage On The Bay - Maryland
8.8 3 reviews

Cottage On The Bay

cottage, Long Beach
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.

Best pet friendly Maryland cottages

Among the 1577 accommodations in Maryland, here are the 4 best pet friendly cottages

Cozy Cottage With Private Dock- Chesapeake Bay/ Cambridge (Pet-friendly) - Maryland
10 19 reviews

Cozy Cottage With Private Dock- Chesapeake Bay/ Cambridge (Pet-friendly)

cottage, Madison
This charming waterfront cottage is located just a short drive from the historic town of Cambridge, Maryland, offering a peaceful escape from the bustle of Madison. The nearby Blackwater National Wildlife Refuge provides ample opportunities for nature lovers to explore.
The cottage features two bedrooms, comfortably accommodating up to six guests, and a fully equipped kitchen with modern appliances. Guests can enjoy the private dock, kayaks, and scenic views, or relax by the fire pit, unwind on the porch or deck, and take advantage of the spa and other amenities.
Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/scotland - Maryland
9.6 17 reviews

Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/scotland

cottage, Piney Point
This Piney Point waterfront holiday home boasts stunning Chesapeake Bay views, is situated in Point Lookout, Southern Maryland, and is a short 3.2km drive from Point Lookout State Park and the Smith Island Ferry.
The 95 square metre property offers two bedrooms, one bathroom, sleeps six, and includes a fully equipped kitchen, Wi-Fi, air conditioning, a garden, parking, and on-site amenities such as a fire pit, kayaks, and fishing/crabbing equipment.
3 Bedroom, Waterfront Cottage On The Shores Of The Chesapeake Bay. - Maryland
9.0 2 reviews

3 Bedroom, Waterfront Cottage On The Shores Of The Chesapeake Bay.

cottage, North Beach
This North Beach holiday home enjoys a beachfront location directly on the boardwalk, offering unparalleled access to the Chesapeake Bay and is within walking distance of local restaurants, shops, and the farmers' market.
The three-bedroom, two-bathroom property sleeps eight guests and features an open-plan layout with high ceilings, a rear patio with fire pit, and internet access; nearby attractions include the Bayside History Museum and Chesapeake Beach Railway Museum.
Lovely 2-bedroom Waterfront Cottage In Charming Wittman - Maryland
9.6 5 reviews

Lovely 2-bedroom Waterfront Cottage In Charming Wittman

cottage, Tilghman Island
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.
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