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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

Cottage 3b/1bath Walk To River & Dining - Maryland
9.6 47 reviews

Cottage 3b/1bath Walk To River & Dining

cottage, Port Deposit
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.
Family And Pet-friendly, Waterfront With Pier - Maryland
10 276 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.
Waterfront River Cottage For 2, Dog-friendly - Maryland
9.5 30 reviews

Waterfront River Cottage For 2, Dog-friendly

apartment, Severna Park
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.
Comfortable Cottage In Gated Community, 5 Mins To Oc And Assateague - Maryland
9.8 54 reviews

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

cottage, West Ocean City
This West Ocean City vacation home, located in the Assateague Pointe community of Berlin, Maryland, is minutes from Ocean City Inlet, Assateague Island, and Frontier Town Water Park.
The 740-square-foot cottage features two bedrooms, one bathroom, sleeps six, and includes a private patio, Smart TVs with Fire Sticks, a fully equipped kitchen, and access to community amenities like multiple pools and a tennis court.

Top cities

Best Maryland cottages with a garden

Private Beach, Pier And Tesla Charger - Stunning Beach Cottage - Maryland
No reviews

Private Beach, Pier And Tesla Charger - Stunning Beach Cottage

cottage, Piney Point
This beachfront cottage in Piney Point offers direct access to the Chesapeake Bay with a private pier for crabbing and fishing, and is close to charter fishing captains for excursions.
This family-friendly rental accommodates up to 8 guests with 3 bedrooms and 2 bathrooms, featuring a gourmet kitchen, complimentary kayaks, stand-up paddleboards, a hammock, fire pit, and four beach cruiser bikes.
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 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.
Relaxing Waterfront Cottage Near St Michaels, Maryland - Maryland
9.8 254 reviews

Relaxing Waterfront Cottage Near St Michaels, Maryland

cottage, Tilghman Island
This charming cottage is located just seven miles from the town of St. Michaels on a peaceful creek off the Chesapeake Bay, making it an ideal spot for a relaxing getaway. Guests consistently rate this property as excellent, highlighting its peaceful setting and convenient location.
The two-bedroom home comfortably accommodates up to four guests and features a well-equipped kitchen, a private pool, a screened porch, and a dock with kayaks for exploring the surrounding waters. Enjoy the beautiful water views, relax in the spa, or take advantage of the nearby attractions, including charming shops and fine dining.
Waterfront Maryland Retreat W/ Dock & Bay View! - Maryland
9.4 12 reviews

Waterfront Maryland Retreat W/ Dock & Bay View!

cottage, Chance
This Chance waterfront home is located 1.6 miles from Shark Fin Shoal and 2.4 miles from Rock Island, with easy access to the Whitehaven Historic District and Mount Vernon Park within 20 miles.
This 2160-square-foot vacation rental boasts four bedrooms, two bathrooms, and accommodates up to nine guests, featuring a fully equipped kitchen, laundry facilities, patio, and charcoal grills; pets are welcome.

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.
Cottage On The Bay - Maryland
8.8 3 reviews

Cottage On The Bay

cottage, Long Beach
This St. Leonard beach house offers proximity to three private beaches within walking distance or a short drive, and is 15 miles from Solomons Island and Prince Frederick.
This family-friendly cottage accommodates four guests with two bedrooms and one bathroom, featuring a full kitchen, air conditioning, a jacuzzi, a garden, parking, and shared amenities like a fire pit and kayaks.
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.
Luxurious 4br, Private Pool, Heated Spa-open Year-round, Near Downtown! - Maryland
10 160 reviews

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

cottage, Ballenger Creek
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.

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

Cliffside Chesapeake Bay Cottage: Pet-friendly, Easy Dc Drive - Maryland
10 1 review

Cliffside Chesapeake Bay Cottage: Pet-friendly, Easy Dc Drive

cottage, Chesapeake Beach
This cottage in Chesapeake Beach is a 5-minute walk from the Chesapeake Bay and a 3-minute drive from Bruce Gabrielson's Surf Art Gallery and Museum and the Chesapeake Beach Railway Museum.
This 300-square-foot rental accommodates two guests with one bedroom and one bathroom, offering air conditioning, internet, and is pet-friendly, providing an ideal base for exploring local attractions and outdoor activities.
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.
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels - Maryland
9.6 139 reviews

Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels

cottage, Easton
This charming cottage is located in St. Michaels, just a short walk from the St. Michaels Museum, Chesapeake Bay Maritime Museum, and St. Michaels Winery. It has received excellent ratings from previous guests.
The 1400 square foot home has two bedrooms and three bathrooms, comfortably accommodating up to five guests. Enjoy modern amenities like air conditioning, a swimming pool, a patio, a fireplace, and a fully equipped kitchen.
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 in Chesapeake Ranch Estates offers stunning views of the Chesapeake Bay and is just a short distance from popular attractions like Middle Hooper Island and Lower Hooper Island. It has received excellent user ratings for its comfortable and well-equipped interior.
The cottage has two bedrooms, one bathroom, and can accommodate up to five guests. It features a fully equipped kitchen, a cozy living room with a fireplace, and a private terrace or balcony. Guests can also enjoy the outdoor amenities, including a garden, barbecue grills, and a fire pit.
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