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Maryland cottages
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1669 Cottages at the best price in Maryland

Best family friendly Maryland cottages

Among the 1669 accommodations in Maryland, here are the 4 best family friendly cottages

Pet Friendly Delightful Waterfront Cottage On Hoopers Island, Md. - Maryland
10 51 reviews
Maryland
22/06 – 25/06
SG$396/nighttotal: SG$1188 (3 )

Pet Friendly Delightful Waterfront Cottage On Hoopers Island, Md.

1 4
cottage , Chesapeake Ranch Estates
This waterfront cottage is located in Fishing Creek, Chesapeake Ranch Estates, just 9 kilometres from Middle Hooper Island and within a 32-kilometre radius of Lower Hooper Island and Blackwater National Wildlife Refuge.
The 65 square metre property offers one bedroom, one bathroom and can accommodate up to four guests, with amenities including a fully equipped kitchen, a terrace, a garden and parking.
Cozy Cottage With Access To And Partially Obstructed Views Of The Bay. - Maryland
9.2 33 reviews
Maryland
11/07 – 16/07
SG$467/nighttotal: SG$2335 (5 )

Cozy Cottage With Access To And Partially Obstructed Views Of The Bay.

3 4
cottage , Calvert Beach
This charming cottage is located in Port Republic, a tranquil rural area near the beach in Calvert Beach, Maryland, within easy reach of Calvert Cliffs and the Chesapeake Beach Railway Museum. It has received excellent reviews from previous guests, highlighting its peaceful setting and convenient location.
The cottage has three bedrooms and two bathrooms, comfortably accommodating up to ten guests. It offers a range of amenities, including a fully equipped kitchen, air conditioning, a jacuzzi, a garden, and parking, as well as access to a beautiful community beach for enjoying the outdoors.
Cottage On The Bay - Maryland
9.9 89 reviews
Maryland
11/07 – 16/07
SG$351/nighttotal: SG$1755 (5 )

Cottage On The Bay

1 4
cottage , Long Beach
This Long Beach holiday home, situated in Saint Leonard, Maryland, is close to three private beaches, 24km from Solomons Island and Prince Frederick, and approximately 80km from Washington, D.C.
The two-bedroom, one-bathroom property sleeps four, boasting a fully equipped kitchen with dishwasher, Jacuzzi access, kayaks and paddleboards, smart TVs, and a washer/dryer; guests can enjoy scenic hilltop views.
Eastern Shore Beach Cottage Get-away - Maryland
10 139 reviews
Maryland
11/07 – 16/07
SG$629/nighttotal: SG$3145 (5 )

Eastern Shore Beach Cottage Get-away

2 4
cottage , Rock Hall
This charming cottage is situated just a short drive from the Eastern Neck Island Wildlife Refuge and 10km from Chestertown, home to Washington College, offering a peaceful escape from the hustle and bustle. It has received excellent reviews from previous guests, making it a popular choice for those looking for a relaxing getaway.
The cottage is spacious, spanning 93 square meters and comfortably accommodating up to five guests. It boasts a fully equipped kitchen, a private garden, a swimming pool, and a spa, as well as direct access to a sandy beach, perfect for families and water sports enthusiasts.

Best Maryland cottages with a garden

Carpenter St. Cottage In The Heart Of St Michaels Village - Large Screened Porch - Maryland
9.8 202 reviews
Maryland
04/09 – 07/09
SG$906/nighttotal: SG$2718 (3 )

Carpenter St. Cottage In The Heart Of St Michaels Village - Large Screened Porch

2 2
cottage , Easton
This charming cottage is situated in St. Michaels, a short walk from the Chesapeake Bay Maritime Museum, St. Michaels Museum, and St. Michaels Winery, making it ideal for exploring the town's rich maritime history and vibrant culture. The cottage has received excellent reviews from previous guests, highlighting its comfortable and convenient features.
The two-bedroom cottage spans 130 square metres and comfortably accommodates up to five guests. It offers a fully equipped kitchen, a private garden, a swimming pool, and a spa, providing everything you need for a relaxing and enjoyable stay.
Rock Creek Cottage, Waterfront, Serene Views - Maryland
10 13 reviews
Maryland
20/07 – 23/07
SG$484/nighttotal: SG$1452 (3 )

Rock Creek Cottage, Waterfront, Serene Views

2 2
cottage , Riviera Beach
This charming cottage is situated in Riviera Beach, Pasadena, just a short distance from the Patapsco River and Chesapeake Bay, offering easy access to Baltimore, Annapolis, and Washington D.C. The cottage is a peaceful retreat with serene views of Rock Creek and access to a dock for fishing or potential boat docking.
The cottage spans 92 square metres and comfortably accommodates four guests in its two bedrooms. It features a fully equipped kitchen with a fridge, microwave oven, and dishwasher, a garden, a spa, and parking.
Private Home In Garrett County, Surrounded By Trees,\n Fields \N And Farmland. - Maryland
10 47 reviews
Maryland
14/12 – 17/12
SG$268/nighttotal: SG$804 (3 )

Private Home In Garrett County, Surrounded By Trees,\n Fields \N And Farmland.

3 5
cottage , Grantsville
This Grantsville holiday home sits on over 3 acres bordering farmland, approximately 11-27km from attractions including Wisp Resort, Deep Creek Lake, and Savage River State Park, and 6km from New Germany Park.
The three-bedroom property, sleeping six, offers a fully equipped kitchen, two bathrooms (one en-suite), a gas fireplace, patio, firepit, Wi-Fi, and is close to hiking, kayaking, and golf at the Winnfield Golf course.
Cozy Cottage With Private Dock- Chesapeake Bay/ Cambridge (Pet-friendly) - Maryland
10 16 reviews
Maryland
11/07 – 16/07
SG$456/nighttotal: SG$2280 (5 )

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

2 4
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.

Frequently asked questions about cottages in Maryland

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

    Maryland offers a fantastic mix of attractions. For history buffs, the Inner Harbour in Baltimore, with its maritime museums and the USS Constellation, is a must. Historic Annapolis, the state capital, boasts beautiful architecture and the United States Naval Academy. Nature lovers should explore Assateague Island National Seashore, famous for its wild horses, or the scenic Chesapeake Bay, perhaps taking a boat tour. The National Aquarium in Baltimore is another popular choice, especially for families.
  • What are the best cottages in Maryland?

    Among the cottages in Maryland, The Heron's Nest At Atlantic Marina, Persimmon Pastures and Family And Pet-friendly - Waterfront With Pier are the most popular ones.

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

    A five-day trip allows for a good exploration. Spend a day in Baltimore, visiting the Inner Harbour and the American Visionary Art Museum. Dedicate a day to Annapolis, exploring its historic district and maybe taking a sailing trip on the Chesapeake Bay. A day trip to Assateague Island National Seashore to see the wild horses is highly recommended. Another day could be spent exploring the Eastern Shore, perhaps visiting charming towns like St Michaels. The final day could be used for relaxation, maybe exploring a local winery in the Frederick area or revisiting a favourite spot.
  • What are the best cottages with a pool in Maryland?

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

    Absolutely! Maryland's Eastern Shore and areas around the Chesapeake Bay are dotted with charming cottages perfect for a relaxing getaway. Ocean City also offers many rental cottages, though these tend to be more geared towards beach holidays. You'll find a variety of options, from rustic cabins to more modern cottages, depending on your preference and budget. Booking in advance, especially during peak season, is advisable.
  • 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 all four seasons. Summers are hot and humid, while winters can be cold, especially in the western parts of the state. Be prepared for rain showers throughout the year. Regarding wildlife, you might encounter deer, foxes, and various bird species. Natural hazards include occasional severe thunderstorms and, along the coast, the risk of hurricanes, particularly during late summer and autumn. Checking weather forecasts before and during your trip is essential.
  • What are the best cottages for families and kids in Maryland?

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

    It depends on the location. Cities like Annapolis and Baltimore have areas that are pedestrian-friendly, with walkable historic districts. However, other areas may require a car for convenient travel. Dedicated cycling paths are becoming more common, but aren't ubiquitous. In more rural areas, cycling may be more challenging due to traffic and road conditions. It's advisable to research specific locations and plan routes accordingly.
  • What are the best pet friendly cottages in Maryland?

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

    Yes, definitely! Explore the Catoctin Mountains for hiking and scenic views. The town of Ellicott City, with its historic mill and charming shops, is a hidden gem. For something unique, visit the National Cryptologic Museum in Fort Meade, which showcases the history of codebreaking. Also, consider exploring Assateague Island's less-visited areas beyond the main beaches.
  • What are the best cottages with parking in Maryland?

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

    Attending local festivals is a great way to interact with Marylanders. Check out events like the Maryland Renaissance Festival for a unique experience, or explore smaller, town-specific festivals throughout the year. Visiting farmers' markets, especially in the summer months, allows you to interact with local producers and learn about regional produce. Many local breweries and wineries also offer opportunities to meet people and learn about their craft.
  • What are the best authentic dishes to taste in Maryland, United States?

    Maryland is known for its Chesapeake Bay seafood. Crab cakes are a must-try, as is steamed blue crabs. Smith Island cake, a layer cake with many thin layers, is another local specialty. For something different, try Berger cookies, a local favourite. Many restaurants throughout the state offer these and other regional dishes.
  • Are there any recommended items to pack for a stay in Maryland, United States?

    Pack comfortable walking shoes, as you'll likely be doing a lot of exploring. Depending on the time of year, pack layers of clothing to adjust to changing temperatures. Sunscreen, insect repellent, and a hat are essential, especially during summer. A reusable water bottle is also recommended, as staying hydrated is important, particularly during warmer months. If you plan on hiking, bring appropriate footwear and gear.

Nearby regions

Best Maryland cottages with a jacuzzi

Among the 1669 accommodations in Maryland, here are the 4 best cottages with a jacuzzi

Hays Beach House - Hot Tub - Private Beach - Maryland
9.8 16 reviews
Maryland
10/09 – 13/09
SG$832/nighttotal: SG$2496 (3 )

Hays Beach House - Hot Tub - Private Beach

5 7
cottage , Piney Point
This five-bedroom cottage is located in Point Lookout, a rural beachside neighbourhood in Scotland, MD, approximately 24 kilometres from Piney Point. The property has consistently received excellent reviews from guests.
The cottage can accommodate up to 12 guests and features a fully equipped gourmet kitchen, a private hot tub with bay views, and a screened porch. Guests can enjoy direct access to a private beach for crabbing, fishing, kayaking, and stand-up paddle boarding, as well as a Tesla charger and contactless check-in.
Watrfnt Cottage @Chesapeakeparadise Kayaks/dogs Ok - Maryland
9.7 275 reviews
Maryland
20/07 – 23/07
SG$522/nighttotal: SG$1566 (3 )

Watrfnt Cottage @Chesapeakeparadise Kayaks/dogs Ok

3 2
cottage , Deale
This charming cottage is situated just 16km from Deale, on the western shore of the Chesapeake Bay, offering a peaceful retreat close to the vibrant city of Annapolis. It has consistently received excellent ratings for its location, cleanliness, and overall experience.
The cottage spans 111 square metres and comfortably accommodates up to 8 guests. It boasts a fully equipped kitchen, a private garden with a fire pit and a pier, and access to kayaks and other watercraft for exploring the nearby creek and Chesapeake Bay.
Cozy Cottage - Maryland
10 1 review
Maryland
20/07 – 23/07
SG$1032/nighttotal: SG$3096 (3 )

Cozy Cottage

4 2
cottage , Dundalk
This Dundalk holiday home is situated within 9.6km of Johns Hopkins Bayview Medical Center, the Baltimore Cruise Terminal, and Johns Hopkins Hospital, offering convenient access to these key locations.
Sleeping eight guests, the four-bedroom, two-bathroom property boasts a fully equipped kitchen with dishwasher, a jacuzzi, private garden, parking, and air conditioning, plus a washing machine and dryer for added convenience.
Cottage On The Bay - Maryland
8.8 3 reviews
Maryland
11/07 – 16/07
SG$314/nighttotal: SG$1570 (5 )

Cottage On The Bay

2 4
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 1669 accommodations in Maryland, here are the 4 best pet friendly cottages

3 Bedroom, Waterfront Cottage On The Shores Of The Chesapeake Bay. - Maryland
8.0 1 review
Maryland
04/09 – 07/09
SG$939/nighttotal: SG$2817 (3 )

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

3 2
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.
Tiny House At St. George Island - Maryland
8.0 4 reviews
Maryland
10/07 – 13/07
SG$295/nighttotal: SG$885 (3 )

Tiny House At St. George Island

2 5
cottage , Piney Point
This cottage, a cosy tiny house, is located in Piney Point, a short distance from the historic Piney Point Lighthouse and Cecil's Old Mill, and close to St. Mary's River State Park.
This accommodation sleeps up to five guests across two bedrooms and offers internet, air conditioning, a kitchen with a fridge and microwave, and exclusive access to a private sandy beach for fishing, crabbing, and picnicking.
Waterfront Cottage For Paddle Boarding, Kayaking, Crabbing, And Fishing - Maryland
9.8 155 reviews
Maryland
20/07 – 23/07
SG$333/nighttotal: SG$999 (3 )

Waterfront Cottage For Paddle Boarding, Kayaking, Crabbing, And Fishing

1 2
cottage , Cobb Island
This Cobb Island waterfront cottage, situated 12.7km from the Potomac River and 13.2km from Aqualand Marina, offers easy access to Chapel Point State Park and Saint Ignatius Church within a 26km radius.
This 62 square metre holiday home sleeps three, boasting a fully equipped kitchen, a terrace, garden, free Wi-Fi, and parking, ideal for exploring the area’s natural beauty and historical sites.
3b/1fb/kitchen, Center Of Town, The Cottage @ The Manor - Maryland
9.6 45 reviews
Maryland
04/09 – 07/09
SG$449/nighttotal: SG$1347 (3 )

3b/1fb/kitchen, Center Of Town, The Cottage @ The Manor

3 2
cottage , Port Deposit
This charming cottage is located just nine miles from Hollywood Casino, Garrett Island Beach, and Perry Point VA Medical Center, offering a peaceful retreat in a scenic riverside location. It has consistently received excellent ratings from previous guests for its cleanliness, location, and overall experience.
The three-bedroom property spans 177 square metres and is ideal for families or groups of friends. It comes equipped with a modern kitchen, a private fenced garden, a fitness centre, a spa tub, and a barbecue grill, providing everything you need for a comfortable and enjoyable stay.
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