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

Beachfront Home Minutes To Downtown Annapolis W Parking & Dog-friendly - Maryland
9.8 45 reviews

Beachfront Home Minutes To Downtown Annapolis W Parking & Dog-friendly

cottage, Annapolis
This charming cottage is located just 4 km from downtown Annapolis and 4.5 km from the US Naval Academy, offering a peaceful escape close to the city's attractions. It has received excellent guest reviews, making it a popular choice for travellers seeking a comfortable and well-equipped stay.
The cottage comfortably sleeps 8 guests and features 3 bedrooms and 2 bathrooms, providing ample space for families or groups. Enjoy the private beach with direct bay access, a gourmet kitchen, a spacious garden, and a range of amenities including paddle boards, life jackets, and a barbecue grill.
Firefly Cottage At The Cape, Hot Tub, Community Beach, Boat Show, Usna Football. - Maryland
10 121 reviews

Firefly Cottage At The Cape, Hot Tub, Community Beach, Boat Show, Usna Football.

cottage, Arnold
This charming cottage is located in Cape Saint Claire, just a short drive from Arnold's attractions, including Sandy Point State Park and Sandy Point Beach. The cottage has received excellent user ratings, making it a popular choice for travellers.
This holiday home offers 61 square metres of space, comfortably accommodating up to 5 guests in its one bedroom and one bathroom. The cottage is equipped with a range of amenities, including a fully fitted kitchen, a spa, a terrace, a garden, parking and Wi-Fi, ensuring a comfortable and enjoyable stay.
Accessible, 3 Season Screened-in Porch, Sauna, Fire Pit, Dog Friendly - Maryland
10 71 reviews

Accessible, 3 Season Screened-in Porch, Sauna, Fire Pit, Dog Friendly

cottage, Stevensville
This Stevensville, Maryland holiday home is conveniently located near several Kent Island wedding venues, within an hour's drive (approx. 80km) of Annapolis, Washington D.C., and Baltimore.
The 111-square-metre property boasts two bedrooms, two bathrooms, sleeping up to six guests, and features a screened-in porch, private sauna, and accessibility features; guests can also hire a chef or artist.
Sunrise Waterfront Cottage In Beautiful Hoopers Island - Maryland
10 88 reviews

Sunrise Waterfront Cottage In Beautiful Hoopers Island

cottage, Chesapeake Ranch Estates
This waterfront cottage is located in Chesapeake Ranch Estates, just 5km from Middle Hooper Island and 8km from Lower Hooper Island, offering a peaceful escape in a picturesque setting. It has received excellent user reviews, making it a popular choice for travellers.
The cottage spans 54 square metres and comfortably accommodates up to 5 guests in its two bedrooms and one bathroom. It includes a fully equipped kitchen, a garden, a terrace, and free Wi-Fi, allowing you to enjoy both indoor and outdoor relaxation, as well as easy access to the surrounding natural beauty.

Top cities

Best Maryland cottages with a garden

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.
Enjoy Fall On Our Big Porch! Check Out Discounts, Bike Storage And Amenities! - Maryland
10 9 reviews

Enjoy Fall On Our Big Porch! Check Out Discounts, Bike Storage And Amenities!

cottage, Williamsport
This Williamsport cottage, situated in the city centre, offers easy access to Whitetail Ski Resort (32km), Washington, D.C. (approx. 240km), and Shenandoah National Park, and is close to Hagerstown Suns Municipal Stadium and Antietam National Battlefield.
The 111-square-metre property sleeps six guests across three bedrooms and two bathrooms, boasting a fully equipped kitchen, garden, Wi-Fi, smart TVs, and parking, with opportunities for birdwatching nearby.
The Yellow Cottage On Harness Creek - Maryland
10 180 reviews

The Yellow Cottage On Harness Creek

cottage, Annapolis
The Yellow Cottage is located on Harness Creek in Hillsmere, a peaceful residential neighbourhood in Annapolis, just a short distance from Jonas Green State Park and the Smithsonian Environmental Research Center. This charming property has received excellent user ratings, making it a popular choice for travellers.
The cottage offers 88 square metres of living space, comfortably accommodating up to six guests in two bedrooms and a living room with a sofa bed. Guests can enjoy a range of amenities, including a fully equipped kitchen, air conditioning, a garden, a spa, and parking, as well as activities such as fishing, crabbing, and kayaking on the creek.

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

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.
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.
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

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.
Pet-friendly Smith Island Cottage W/ Golf Cart! - Maryland
10 23 reviews

Pet-friendly Smith Island Cottage W/ Golf Cart!

cottage, Smith Island
This Smith Island beach house, near Terrapin Sand Point, offers easy access to the beach.
The 137 square metre (1475 square feet) self-catering property sleeps four, boasting two bedrooms, a bathroom, a fully equipped kitchen, Wi-Fi, and on-site parking; plus foosball and games for entertainment.
Oyster Cottage  - Walk To Shops , Mainstay Music Venue And The Bay! - Maryland
9.6 14 reviews

Oyster Cottage - Walk To Shops , Mainstay Music Venue And The Bay!

cottage, Rock Hall
Oyster Cottage is a charming holiday home situated just a short walk from the waterfront in Rock Hall, offering easy access to shops, restaurants, and entertainment. The cottage consistently receives excellent reviews from guests, highlighting its comfortable and convenient location.
The property features two bedrooms, accommodating up to seven guests, making it ideal for families or groups of friends. The cottage offers a range of amenities including a fully equipped kitchen, a private garden, and a patio for outdoor dining, ensuring a relaxing and enjoyable stay.
Beautiful Remodeled Downtown Frederick Cottage (Pet-friendly) - Maryland
9.9 300 reviews

Beautiful Remodeled Downtown Frederick Cottage (Pet-friendly)

cottage, Frederick
This charming cottage is located in Frederick, just a short walk from Baker Park and Frederick Memorial Hospital, and within 1 kilometer of Carroll Creek Linear Park and Hood College, offering easy access to both nature and cultural attractions. The cottage consistently receives excellent ratings for its location, cleanliness, and overall experience.
The cottage has two bedrooms and one bathroom, comfortably accommodating up to four guests. It features a fully equipped kitchen, a private patio, a garden, a jetted tub, and a fitness centre, providing everything you need for a relaxing and enjoyable stay.
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