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Maryland cottages
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1669 Best cottages in Maryland

Best family friendly Maryland cottages

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

Peaceful Suite On The Water "Osprey." Sunrise Over The River From Your Porch. - Maryland
9.0 8 reviews
Maryland
07/30 – 07/31
$285/nightfor 1 night

Peaceful Suite On The Water "Osprey." Sunrise Over The River From Your Porch.

1 2
cottage , Benedict
This Benedict, Maryland beach house boasts a unique beachfront location with over 500 feet of private beach and a 400-foot pier, near the Dr. Samuel A. Mudd House Museum and Drum Point Lighthouse.
This one-bedroom, one-bathroom vacation rental sleeps six, featuring a queen bed, bunk beds, a sleeper sofa, a full kitchen with a fridge and microwave, air conditioning, a terrace, a garden, a spa, and a gas grill; enjoy nearby Walter's Walk sandbar for sunset viewing.
The Cottage At Merryland Farm - Maryland
10 6 reviews
Maryland
08/01 – 08/30
$174/nighttotal: $5046 (29 )

The Cottage At Merryland Farm

1 2
cottage , Kingsville
This 800-square-foot cottage rental near Hydes, Baltimore County, provides easy access to Oregon Ridge Nature Center, Ladew Topiary Gardens, and wineries.
The one-bedroom, one-bathroom house sleeps three, features a full kitchen with a refrigerator and microwave, air conditioning, and a private garden; well-behaved dogs are allowed with prior approval.
Cozy, Unique, Historic Registered Cottage On The Corsica River! - Maryland
10 7 reviews
Maryland
07/20 – 07/23
$258/nighttotal: $774 (3 )

Cozy, Unique, Historic Registered Cottage On The Corsica River!

1 2
cottage , Centreville
This Centreville cottage, located 0.9 miles from the Hazel Miner Monument and within a 9-mile radius of attractions like Cassinelli Winery & Vineyards and Wye Oak State Park, offers a convenient base for exploring the area. This one-bedroom, one-bathroom home sleeps four and features a fully equipped kitchen, air conditioning, a terrace, a garden, and parking, plus on-site barbecue grills for outdoor relaxation.
Check Out Our Rental Discounts! 3bd-2bath, Sleeps 6, 1st Floor Master & Bath - Maryland
10 8 reviews
Maryland
07/10 – 07/13
$290/nighttotal: $870 (3 )

Check Out Our Rental Discounts! 3bd-2bath, Sleeps 6, 1st Floor Master & Bath

3 5
cottage , Williamsport
This Williamsport cottage, located in the city center near the Potomac River, offers easy access to Hagerstown Suns Municipal Stadium and Antietam National Battlefield.
The 1190-square-foot three-bedroom house sleeps six, featuring a fully equipped kitchen, two bathrooms, three smart TVs, WiFi, a washer/dryer, and a private garden; nearby recreational activities include birdwatching and hiking.

Top cities

Best Maryland cottages with a garden

Eastern Shore Beachfront Cottage With Stunning Sunset Views! - Maryland
10 9 reviews
Maryland
07/20 – 07/23
$614/nighttotal: $1842 (3 )

Eastern Shore Beachfront Cottage With Stunning Sunset Views!

3 4
cottage , Butlertown
This three-bedroom, three-bathroom vacation home in Worton, Maryland, near Still Pond Creek, is two miles from the Old Coast Guard Station beach and Betterton Historic District.
The 1910-square-foot house features a private beach access with kayak and bike rentals, a well-equipped kitchen, and multiple indoor/outdoor relaxation areas, accommodating up to six guests.
Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/scotland - Maryland
9.6 14 reviews
Maryland
08/15 – 08/17
$385/nighttotal: $770 (2 )

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

2 2
cottage , Piney Point
This Piney Point waterfront cottage, located in Point Lookout, Southern Maryland, offers stunning Chesapeake Bay views and is minutes from Point Lookout State Park and the Smith Island Ferry.
The 1020-square-foot home features two bedrooms, one bathroom, sleeps six, and includes a fully equipped kitchen, high-speed Wi-Fi, air conditioning, a private dock, fire pit, and Adirondack chairs.
Charming Intown Cottage  The Ultimate Walkable Getaway Steps From Downtown! - Maryland
9.6 60 reviews
Maryland
08/15 – 08/17
$310/nighttotal: $620 (2 )

Charming Intown Cottage The Ultimate Walkable Getaway Steps From Downtown!

1 2
cottage , Easton
This cottage is located in the downtown St. Michaels city center, offering immediate walkability to shops, dining, the St. Michaels Museum, and the Classic Motor Museum, situated on a quiet street for a peaceful getaway. This 900 square foot rental accommodates two guests with one bedroom and one bathroom, featuring air conditioning, a full kitchen with a fridge, microwave, and dishwasher, a private fenced backyard, an enclosed front porch, and is near opportunities for jet skiing, kayaking, and motor boating.
Beautiful Waterfront 2-bedroom Cottage In Tranquil Piney Point With Wifi, Ac - Maryland
10 5 reviews
Maryland
07/03 – 07/05
$347/nighttotal: $694 (2 )

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

2 4
cottage , Piney Point
This Piney Point waterfront cottage offers two bedrooms, one bathroom, and sleeps six, providing easy access to the Piney Point Lighthouse and Patuxent River Naval Air Museum.
The fully equipped kitchen includes a refrigerator, microwave, stove, and cooktop; amenities include air conditioning, Wi-Fi, laundry facilities, and a BBQ grill, plus smart TVs in each bedroom.

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 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
07/17 – 07/24
$1081/nighttotal: $7567 (7 )

Hays Beach House - Hot Tub - Private Beach

5 5
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.
Block To Beach! Fossil Hunting, Hot Tub, Coffee Bar, Screened Deck, 1hr To Dc - Maryland
10 20 reviews
Maryland
08/11 – 08/21
$277/nighttotal: $2770 (10 )

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

2 2
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.
Luxurious 4br, Private Pool, Heated Spa-open Year-round, Near Downtown! - Maryland
10 152 reviews
Maryland
12/14 – 12/17
$376/nighttotal: $1128 (3 )

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

4 5
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.
Cottage On The Bay - Maryland
9.9 89 reviews
Maryland
07/11 – 07/16
$252/nighttotal: $1260 (5 )

Cottage On The Bay

1 4
cottage , Long Beach
This Long Beach vacation home, located in Saint Leonard, Maryland, is a short drive from Solomons Island and Prince Frederick, offering easy access to three private beaches (with provided parking passes for two).
The two-bedroom, one-bathroom house sleeps four, features a fully equipped kitchen with a dishwasher and Fiestaware, a Jacuzzi, and access to shared kayaks, paddleboards, and a fire pit; two 43-inch smart TVs and a 55-inch smart TV are also available.

Neighborhoods and points of interest in Maryland

Best pet friendly Maryland cottages

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

Accessible, 3 Season Screened-in Porch, Sauna, Fire Pit, Dog Friendly - Maryland
10 68 reviews
Maryland
06/22 – 06/25
$641/nighttotal: $1923 (3 )

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

2 4
cottage , Stevensville
This Stevensville, Maryland coastal cottage, a short drive from Annapolis and easily accessible to Kent Island wedding venues, offers convenient proximity to Queenstown Harbor Golf Links and Paul Reed Smith Guitars.
This 1190-square-foot vacation home features two bedrooms, two bathrooms, and accommodates six guests, boasting a screened porch with fireplace, a private barrel sauna, and outdoor amenities including a BBQ grill and firepit.
Potomac Riverfront! Home Near St Clements Island - Maryland
Maryland
07/07 – 08/07
$230/nighttotal: $7130 (31 )

Potomac Riverfront! Home Near St Clements Island

2 4
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.
Charming 1br Cottage W/ Wifi, Ac In Wonderful Wye Mills - Maryland
9.2 7 reviews
Maryland
08/11 – 08/21
$121/nighttotal: $1210 (10 )

Charming 1br Cottage W/ Wifi, Ac In Wonderful Wye Mills

2 2
cottage , Queenstown
This Queenstown, Maryland cottage is conveniently located near the Avalon Theatre and The Third Haven Friends Meeting House, offering easy access to area attractions like the Hazel Miner Monument and Adkins Arboretum.
This two-bedroom, one-bathroom house sleeps four guests and features a fully equipped kitchen (fridge, microwave), air conditioning, Wi-Fi, a terrace, garden, parking, and a washer/dryer; pets are welcome.
Lovely 2-bedroom Waterfront Cottage In Charming Wittman - Maryland
9.0 2 reviews
Maryland
06/22 – 06/25
$406/nighttotal: $1218 (3 )

Lovely 2-bedroom Waterfront Cottage In Charming Wittman

2 4
cottage , Tilghman Island
This Wittman cottage is located approximately 15-16 minutes by car from St. Michaels Marina, the Chesapeake Bay Maritime Museum, Perry Cabin Park, and Back Creek Park, offering convenient access to maritime attractions and recreational areas. This 2-bedroom, 1-bathroom rental accommodates up to 4 guests and includes amenities such as air conditioning and Wi-Fi, with pets welcome.
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