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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

Waterfront Getaway- Charming Waterfront Cottage On St Clements Bay - Maryland
10 79 reviews

Waterfront Getaway- Charming Waterfront Cottage On St Clements Bay

cottage, Leonardtown
The Little Red Oyster House is a charming cottage located just a short drive from Leonardtown, offering a peaceful waterfront escape in the rural area of Abell. It has received excellent user ratings, making it a popular choice for travelers seeking a relaxing getaway.
This 3-bedroom, 2-bathroom home comfortably accommodates up to 6 guests. You'll find a fully equipped kitchen, spacious living room, and a relaxing terrace with breathtaking views. Enjoy kayaking, canoeing, fishing, and exploring the nearby attractions, all while taking advantage of amenities like air conditioning, internet, and a spa.
"Serenity"-st. Patrick's Creek W/ Private Pier - Maryland
10 2 reviews

"Serenity"-st. Patrick's Creek W/ Private Pier

cottage, Cobb Island
This family-friendly Cobb Island cottage, located in Avenue, Maryland, is within six miles of Saint Clements Island State Park, Port Sunlight Beach, and the Saint Clements Island-Potomac River Museum.
This 1,960-square-foot vacation home boasts four bedrooms, four bathrooms, and can comfortably accommodate eight guests, featuring amenities such as a fully equipped kitchen, free Wi-Fi, a private balcony, and a cozy fireplace.
Charming Waterfront Pier And Cozy Patio - Delightful River Escape - Maryland
No reviews

Charming Waterfront Pier And Cozy Patio - Delightful River Escape

cottage, Severna Park
This cottage is located on a 3-acre property overlooking the Magothy River in Severna Park, offering waterfront pier access and a peaceful retreat just 11 miles from downtown Annapolis and the U.S. Naval Academy.
This newly-furnished 1-bedroom, 1-bathroom accommodation sleeps 2 guests and features a full kitchen, air conditioning, internet, and a shared game room, with dogs welcome for a fee.
Soul Oasis - Home On The Chesapeake Bay - Maryland
10 57 reviews

Soul Oasis - Home On The Chesapeake Bay

cottage, Chesapeake Ranch Estates
This charming cottage in Lusby is a short walk from the Chesapeake Bay beach and is close to Cove Point and Drum Point Lighthouses. The cottage has received excellent ratings from previous guests.
The cottage features a spiral staircase leading to a loft with a queen-size bed and a small balcony, and it can accommodate up to 5 guests. The cottage includes a terrace, garden, parking, air conditioning, a kitchen with a fridge and microwave, and a basement with beach chairs, a washer, and a dryer.

Top cities

Best Maryland cottages with a garden

C&o Canal Potomac River Cottage - Maryland
10 65 reviews

C&o Canal Potomac River Cottage

cottage, Mercersville
This family-friendly cottage is located in Sharpsburg, just a short distance from the Chesapeake and Ohio Canal National Historic Park and the Potomac River, offering a peaceful setting for a relaxing getaway. Guests consistently rate this property as excellent.
The cozy cabin has three bedrooms and can accommodate up to six guests, making it perfect for families or groups of friends. Enjoy modern amenities like free Wi-Fi, a fireplace, a fully equipped kitchen, and a terrace with barbecue grills for outdoor dining.
Firefly Cottage At The Cape, Hot Tub, Community Beach, Boat Show, Usna Football. - Maryland
10 118 reviews

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

cottage, Arnold
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.
Chesapeake Cottages- 2 Quaint Waterfront Retreats - Maryland
9.6 23 reviews

Chesapeake Cottages- 2 Quaint Waterfront Retreats

cottage, Riviera Beach
This waterfront cottage is located in Pasadena, Maryland, just a short drive from Baltimore attractions like the Cruise Terminal and Inner Harbor Marina. The cottage has received excellent user ratings for its comfortable accommodations and beautiful location.
The property features two separate cottages, providing plenty of space for larger groups. Both cottages include fully equipped kitchens, a spacious garden, a private pier, and a variety of water activities, including fishing, crabbing, and paddleboarding.
Family And Pet-friendly, Waterfront With Pier - Maryland
10 274 reviews

Family And Pet-friendly, Waterfront With Pier

cottage, Madison
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.

Frequently Asked Questions about cottages in Maryland

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

    Maryland offers a ton of amazing sights! For history buffs, the Inner Harbor in Baltimore with the National Aquarium and the USS Constellation is a must. History comes alive at the Antietam National Battlefield. Nature lovers should head to Assateague Island National Seashore for wild horses and beautiful beaches, or explore the Chesapeake Bay. Don't forget the charming town of St. Michaels on the Eastern Shore.
  • What are the best cottages in Maryland?

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

    A five-day trip allows for a good mix! Spend a day or two exploring Baltimore's Inner Harbor, visiting the museums and enjoying the waterfront. Then, head east to the Chesapeake Bay region, perhaps visiting Annapolis, the state capital, and exploring its historic district and maritime museum. A day trip to Assateague Island for some beach time and wildlife viewing is perfect. Consider a visit to Frederick, a charming city with a historic downtown, before heading back to Baltimore for your departure.
  • What are the best cottages with a pool in Maryland?

  • Is Maryland a good destination to rent a cottage?

    Absolutely! The Eastern Shore of Maryland, especially areas near the Chesapeake Bay, is dotted with charming cottages perfect for a relaxing getaway. Ocean City also offers many rental cottages, especially near the beach. You'll find a variety of options, from cozy smaller cottages to larger ones suitable for families or groups.
  • What are the best cottages with a jacuzzi in Maryland?

  • What weather, wildlife, or natural hazards might affect travelers in Maryland?

    Maryland's weather can be unpredictable. Summers are hot and humid, while winters can be chilly, especially in the western mountains. Be prepared for rain showers throughout the year. Wildlife encounters are generally limited to birds, deer, and maybe some squirrels. Natural hazards include occasional severe thunderstorms and the potential for hurricanes, especially along the coast, during hurricane season (June 1st to November 30th).
  • What are the best cottages for families and kids in Maryland?

  • Is Maryland pedestrian and cyclist-friendly?

    Maryland's pedestrian and cyclist friendliness varies by location. Cities like Baltimore and Annapolis have areas that are walkable, but others require a car. The many dedicated bike paths along the Chesapeake Bay and other scenic areas are great for cycling. However, always check local conditions and traffic before venturing out on foot or by bike.
  • What are the best pet friendly cottages in Maryland?

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

    Attending local festivals is a great way to connect with Marylanders. Many towns host summer festivals with live music, local crafts, and food. Visiting farmers' markets, especially in smaller towns, is another excellent way to meet locals and sample regional produce. Consider exploring the many historic districts in towns like Annapolis or St. Michaels; you're sure to encounter friendly locals.
  • What are the best cottages with parking in Maryland?

  • What are the best authentic dishes to taste in Maryland?

    Maryland's cuisine is heavily influenced by the Chesapeake Bay. Crab cakes are a must-try, but be sure to look for ones made with mostly lump crab meat. Chesapeake Bay oysters are another local delicacy. Smith Island Cake, a unique layered cake, is a wonderful dessert option. Don't forget the regional variations of barbecue, which differ from other parts of the country.
  • What are some recommended items to pack for a stay in Maryland?

    Pack comfortable walking shoes, as you'll likely be doing a lot of exploring. Bring layers of clothing, as the weather can change quickly. Sunscreen, insect repellent, and a hat are essential, especially during the warmer months. If you plan on visiting the beaches, bring swimwear and beach towels. Finally, don't forget a camera to capture all the amazing sights!

Nearby regions

Best Maryland cottages with jacuzzi

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

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 pet-friendly cottage in Woolford, Maryland, offers a waterfront location with on-site kayaking and is a 13-minute drive to Blackwater National Wildlife Refuge and a 14-minute drive to Harriet Tubman Underground Railroad National Historical Park.
This 1600 square foot vacation home features 3 bedrooms, 2 bathrooms, accommodates up to 5 guests, and includes amenities such as Wi-Fi, air conditioning, a garden, parking, and an outdoor living space with a fire pit.
Private Beach And Inviting Hot Tub - Charming Coastal Oasis - Maryland
No reviews

Private Beach And Inviting Hot Tub - Charming Coastal Oasis

cottage, Piney Point
This beachfront cottage in Piney Point offers direct access to the Chesapeake Bay, ideal for crabbing, fishing, and enjoying the water.
Accommodating up to 12 guests, this 5-bedroom, 3-bathroom residence features a gourmet kitchen, hot tub with bay views, screened porch, private deck, kayaks, a stand-up paddleboard, and a Tesla charger.
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 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 - Hot Tub - Private Beach - Maryland
9.6 17 reviews

Hays Beach House - Hot Tub - Private Beach

cottage, Piney Point
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.

Neighborhoods and points of interest in Maryland

Best pet friendly Maryland cottages

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

Charming 1-bedroom Cottage With Ac In Cozy Harwood - Maryland
10 3 reviews

Charming 1-bedroom Cottage With Ac In Cozy Harwood

cottage, Riva
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.
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 located in Rock Hall, just a short walk from the waterfront, shops, restaurants, and entertainment. The cottage has received excellent user ratings and is a great option for families and pet owners.
The cottage features two bedrooms, one bathroom, and can accommodate up to seven guests. The cottage offers a well-equipped kitchen, a spacious living area, a relaxing jacuzzi, and a private outdoor space with a patio, a grill, and a garden.
Potomac Riverfront! Home Near St Clements Island - Maryland
10 1 review

Potomac Riverfront! Home Near St Clements Island

cottage, Cobb Island
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.
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 waterfront cabin is located in Cambridge, Maryland, a small town with local shops and restaurants, just 3 miles from a public boat ramp and 30 minutes from Easton and St. Michaels. The cottage is situated on 2 acres of land and offers a private dock, perfect for fishing, crabbing, and boating.
This cozy cabin can comfortably accommodate up to 6 guests in its two bedrooms and one bathroom. Enjoy the fully equipped kitchen, laundry facilities, outdoor fire pit, kayaks, and access to the Blackwater National Wildlife Refuge for birdwatching and nature walks.
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