Cottages in Maryland

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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

Waterfront Sunsets, Fishing, Boating, And Crabs! Paxs River, Budds Creek Mir. - Maryland
10 18 reviews
Maryland
11/07 – 16/07
A$400/nighttotal: A$2000 (5 )

Waterfront Sunsets, Fishing, Boating, And Crabs! Paxs River, Budds Creek Mir.

2 4
cottage , Rock Point
This two-bedroom Rock Point cottage, located in Chaptico, Maryland, is within 15km of Country Lakes Community Park, Maryland International Raceway, and Budds Motorcross Speedway, and 20km from Port Sunlight Beach and The Shoppes at McIntosh.
Sleeping up to six guests, the self-catering property boasts a fully equipped kitchen, a patio, air conditioning, Wi-Fi, and concierge services, plus parking and barbecue facilities are available.
Waterfront Getaway- Charming Waterfront Cottage On St Clements Bay - Maryland
10 73 reviews
Maryland
08/08 – 15/08
A$586/nighttotal: A$4102 (7 )

Waterfront Getaway- Charming Waterfront Cottage On St Clements Bay

3 2
cottage , Leonardtown
The Little Red Oyster House is situated in Abell, a peaceful waterfront location just a short drive from the historic town of Leonardtown. This charming cottage consistently receives excellent reviews from guests, highlighting its tranquil atmosphere and idyllic setting.
The property offers three bedrooms and two bathrooms, accommodating up to six guests comfortably. Guests can enjoy a fully equipped kitchen, a spacious living area, a private garden, a relaxing spa, and a terrace with stunning views of St. Clements Bay.
Cozy, Unique, Historic Registered Cottage On The Corsica River! - Maryland
10 7 reviews
Maryland
19/08 – 23/08
A$371/nighttotal: A$1484 (4 )

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

1 3
cottage , Centreville
This Centreville cottage is situated 1.5 km from the Hazel Miner Monument and within 15 km of Cassinelli Winery and Vineyards, Wye Oak State Park, and Queenstown Premium Outlets.
The self-catering property sleeps four guests in one bedroom and one bathroom, boasting a fully equipped kitchen, in-unit laundry, free Wi-Fi, a balcony, and a garden with barbecue facilities.
Private Beach Front Getaway At The Sunshine Beach Cottage. - Maryland
9.8 80 reviews
Maryland
03/09 – 07/09
A$774/nighttotal: A$3096 (4 )

Private Beach Front Getaway At The Sunshine Beach Cottage.

3 4
cottage , Piney Point
This charming beach house is situated just 8 kilometres from Point Lookout State Park and within a 19 kilometre radius of several other attractions, offering easy access to the region's natural beauty and historical sites. It has received excellent user ratings, making it a popular choice for families and groups.
The two-bedroom property spans 91 square metres and comfortably accommodates up to 8 guests. The cottage features a range of amenities, including a fully equipped kitchen, a cosy fireplace, a terrace, and a garden, ensuring a relaxing and enjoyable stay.

Top cities

Best Maryland cottages with a garden

Charming Waterfront Cottage With Private Dock. Close To Annapolis & Usna - Maryland
10 225 reviews
Maryland
19/07 – 30/07
A$575/nighttotal: A$6325 (11 )

Charming Waterfront Cottage With Private Dock. Close To Annapolis & Usna

3 2
cottage , Mayo
This family-friendly cottage is situated in Edgewater, Mayo, just a short drive from Triton Beach and other local attractions. It enjoys an excellent user rating, making it a popular choice for families seeking a relaxing getaway.
The three-bedroom property, spanning 172 square metres, comfortably accommodates up to 11 guests. Enjoy a fully equipped kitchen, a spacious garden, and a terrace, perfect for al fresco dining and taking in the scenic views.
Cozy Cottage With Access To And Partially Obstructed Views Of The Bay. - Maryland
9.2 33 reviews
Maryland
11/07 – 16/07
A$517/nighttotal: A$2585 (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.
Check Out Our Rental Discounts! 3bd-2bath, Sleeps 6, 1st Floor Master & Bath - Maryland
10 8 reviews
Maryland
01/08 – 30/08
A$225/nighttotal: A$6525 (29 )

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

3 2
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.
New! Private Luxury Spa Hot Tub Retreat With Ping Pong - Maryland
10 1 review
Maryland
10/07 – 13/07
A$2283/nighttotal: A$6849 (3 )

New! Private Luxury Spa Hot Tub Retreat With Ping Pong

3 5
cottage , Severn
This Severn holiday flat is situated 12.8 kilometres from Arundel Mills Mall and 33.8 kilometres from Oriole Park at Camden Yards, offering proximity to outdoor pursuits such as hiking and biking.
This spacious 118 square metre residence accommodates up to six guests with three bedrooms and three bathrooms, featuring a hot tub, private terrace, on-site parking, Wi-Fi, air conditioning, a fireplace, a dedicated workspace, a fully equipped kitchen, and an in-unit washer and dryer.

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

Firefly Cottage At The Cape, Hot Tub, Community Beach, Strawberry Festival, Usna - Maryland
10 108 reviews
Maryland
20/07 – 23/07
A$506/nighttotal: A$1518 (3 )

Firefly Cottage At The Cape, Hot Tub, Community Beach, Strawberry Festival, Usna

1 2
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.
Luxurious 4br, Private Pool, Heated Spa-open Year-round, Near Downtown! - Maryland
10 152 reviews
Maryland
14/12 – 17/12
A$535/nighttotal: A$1605 (3 )

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

4 5
cottage , Ballenger Creek
This charming cottage is located in Ballenger Creek, just 10 kilometres from the historic centre of Frederick, offering a peaceful retreat in a quiet, secluded area. It has received excellent user ratings, reflecting its high standard of comfort and service.
The cottage spans 186 square metres and comfortably accommodates up to eight guests, with four bedrooms and a bathroom. It offers a range of amenities, including a swimming pool, a spa, a terrace, a garden, and a gourmet kitchen, providing everything you need for a relaxing and enjoyable stay.
Hays Beach House - Hot Tub - Private Beach - Maryland
9.8 16 reviews
Maryland
22/09 – 25/09
A$833/nighttotal: A$2499 (3 )

Hays Beach House - Hot Tub - Private Beach

5 3
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
A$578/nighttotal: A$1734 (3 )

Watrfnt Cottage @Chesapeakeparadise Kayaks/dogs Ok

3 4
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.

Best pet friendly Maryland cottages

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

Lovely 2-bedroom Waterfront Cottage In Charming Wittman - Maryland
9.0 2 reviews
Maryland
04/09 – 07/09
A$621/nighttotal: A$1863 (3 )

Lovely 2-bedroom Waterfront Cottage In Charming Wittman

2 2
cottage , Tilghman Island
This Wittman holiday home offers a convenient base on Tilghman Island, located within a 2.4 to 2.6 kilometre drive of Perry Cabin Park, Back Creek Park, St. Michaels Marina, and the Chesapeake Bay Maritime Museum, with Wittman Park and CL Open Field also easily accessible for nature enthusiasts.
This two-bedroom property accommodates up to four guests, providing essential amenities including Wi-Fi, air conditioning, a dryer, and towels, and is a short drive from cultural sites like the Tilghman Watermen’s Museum and outdoor recreational areas such as Phillips Wharf Environmental Center.
Waterfront Cottage In Beautiful Hoopers Island - Maryland
10 84 reviews
Maryland
04/09 – 07/09
A$464/nighttotal: A$1392 (3 )

Waterfront Cottage In Beautiful Hoopers Island

2 2
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.
3 Bedroom, Waterfront Cottage On The Shores Of The Chesapeake Bay. - Maryland
8.0 1 review
Maryland
04/09 – 07/09
A$1039/nighttotal: A$3117 (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.
Eastern Shore Beach Cottage Get-away - Maryland
10 139 reviews
Maryland
20/07 – 23/07
A$729/nighttotal: A$2187 (3 )

Eastern Shore Beach Cottage Get-away

2 2
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.
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