Cottages in Maryland at the best prices

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Maryland cottages
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1577 Best cottages in Maryland

Best family friendly Maryland cottage rentals

Among the 1577 accommodations in Maryland, here are the 4 best family friendly cottage rentals

Private Beach Front Getaway At The Sunshine Beach Cottage. - Maryland
9.8 87 reviews

Private Beach Front Getaway At The Sunshine Beach Cottage.

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.
Cottage:walkable 2 Everything-super Clean-downtown - Maryland
9.9 300 reviews

Cottage:walkable 2 Everything-super Clean-downtown

cottage, Frederick
This charming cottage is located in Frederick, just a short walk from Baker Park and Frederick Memorial Hospital, and within 1 kilometer of Carroll Creek Linear Park and Hood College, offering easy access to both nature and cultural attractions. The cottage consistently receives excellent ratings for its location, cleanliness, and overall experience.
The cottage has two bedrooms and one bathroom, comfortably accommodating up to four guests. It features a fully equipped kitchen, a private patio, a garden, a jetted tub, and a fitness centre, providing everything you need for a relaxing and enjoyable stay.
"Family Friendly Getaway" - Close To Assateague / Downtown Berlin / O.c. - Maryland
10 117 reviews

"Family Friendly Getaway" - Close To Assateague / Downtown Berlin / O.c.

cottage, Berlin
This Berlin, Maryland cottage is situated 0.4 kilometres from Berlin's town centre, 11.3 kilometres from Ocean City, and 11.3 kilometres from Assateague Island National Seashore.
Sleeping six, this three-bedroom, two-bathroom holiday home boasts a newly renovated kitchen, ample parking for recreational vehicles, a private picnic area with grill and fire pit, and features including a wet bar, two TVs, and Wi-Fi.
Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/scotland - Maryland
9.6 17 reviews

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

cottage, Piney Point
This Piney Point waterfront holiday home boasts stunning Chesapeake Bay views, is situated in Point Lookout, Southern Maryland, and is a short 3.2km drive from Point Lookout State Park and the Smith Island Ferry.
The 95 square metre property offers two bedrooms, one bathroom, sleeps six, and includes a fully equipped kitchen, Wi-Fi, air conditioning, a garden, parking, and on-site amenities such as a fire pit, kayaks, and fishing/crabbing equipment.

Best Maryland cottages with a garden

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 holiday home is situated in the Assateague Pointe community of Berlin, Maryland, a short distance (a few kilometres) from Ocean City Inlet, Assateague Island, and Frontier Town water park.
The 69 square metre self-catering property sleeps six adults across two bedrooms and one bathroom, boasting a private patio, community swimming pool, tennis court, and access to a catch-and-release pond with paddle boats.
Beautiful Farmstay Hill Cottage And Tiny Equipped Camper In Maryland - Maryland
No reviews

Beautiful Farmstay Hill Cottage And Tiny Equipped Camper In Maryland

cottage, Darnestown
This rural retreat offers a tranquil farm setting near Germantown, providing convenient access to the Potomac River, Seneca Creek State Park, and Sugarloaf Mountain, with Washington D.C. and Baltimore approximately 40-64 kilometres away.
This 3-bedroom, 2-bathroom holiday cottage accommodates up to 6 guests and features air conditioning, a swimming pool, a garden, a tennis court, and a well-equipped kitchen, with optional horse boarding and farm experiences available for an additional fee.
𝑩𝑨𝒀 𝑺𝑰𝑫𝑬 𝑹𝑬𝑻𝑹𝑬𝑨𝑻, On The Sands Of The 𝐂𝐇𝐄𝐒𝐀𝐏𝐄𝐀𝐊𝐄 𝐁𝐀𝐘 - Maryland
10 138 reviews

𝑩𝑨𝒀 𝑺𝑰𝑫𝑬 𝑹𝑬𝑻𝑹𝑬𝑨𝑻, On The Sands Of The 𝐂𝐇𝐄𝐒𝐀𝐏𝐄𝐀𝐊𝐄 𝐁𝐀𝐘

cottage, Piney Point
This charming cottage is situated in Point Lookout, a peaceful neighbourhood in Scotland, Maryland, just 13km from St. Mary’s College and less than 3 hours from Washington D.C. It has received excellent reviews from previous guests, making it a popular choice for travellers seeking a relaxing getaway.
The cottage offers three bedrooms and sleeps up to eight guests comfortably. It features modern amenities such as a fully equipped kitchen, a private beach, a screened-in porch, kayaks, fishing poles, and a Jacuzzi, ensuring a memorable stay.
Be Persuaded To Experience This Vintage Cottage By The Sassa - Maryland
9.4 15 reviews

Be Persuaded To Experience This Vintage Cottage By The Sassa

cottage, Galena
This charming cottage is located on the banks of a river, just 20 kilometres from attractions like Dutch Country Farmers Market, Betterton Beach, and Washington College. It has received excellent reviews from previous guests.
This four-bedroom property comfortably sleeps eight guests and includes two bathrooms. The cottage offers a fully-equipped kitchen, a garden, barbecue facilities, a terrace, free Wi-Fi, and parking.

Frequently Asked Questions about cottages in Maryland

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

    Maryland offers a diverse range of attractions. For history buffs, the Inner Harbor in Baltimore, with the National Aquarium and the historic Fort McHenry, is a must-see. History lovers should also explore Annapolis, Maryland's charming state capital, with its historic district and the United States Naval Academy. Nature enthusiasts will enjoy Assateague Island National Seashore, known for its wild horses, and the Chesapeake Bay, offering opportunities for boating, fishing, and crabbing. The Catoctin Mountain Park provides hiking trails and scenic views.
  • What are the best cottage rentals in Maryland?

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

    A five-day trip could involve spending two days exploring Baltimore's Inner Harbor, visiting the National Aquarium and Fort McHenry. Dedicate a day to Annapolis, touring the historic district and the Naval Academy. Spend another day at Assateague Island National Seashore, enjoying the beach and wildlife. The remaining day could be used to explore a specific interest, such as hiking in Catoctin Mountain Park or visiting a local museum like the Walters Art Museum in Baltimore.
  • What are the best cottage rentals with a pool in Maryland?

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

    Yes, Maryland is excellent for cottage rentals. The Eastern Shore offers numerous charming cottages near the Chesapeake Bay, perfect for a relaxing getaway. Ocean City also has many rental cottages, ideal for beach vacations. The mountains of Western Maryland provide a different setting with rustic cottages available for rent.
  • What are the best cottage rentals with a jacuzzi in Maryland?

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

    Maryland's pedestrian and cyclist friendliness varies by location. Cities like Annapolis and Baltimore have areas that are walkable, but car use is often necessary. Dedicated bike paths exist in some areas, particularly near the Chesapeake Bay and in parks like the Patapsco Valley State Park. However, planning your routes carefully is essential, especially when cycling on roads with traffic.
  • What are the best cottage rentals for families and kids in Maryland?

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

    Yes, there are many. Explore the abandoned town of Boonsboro, Maryland, which has a fascinating history. Visit the unique rock formations at Cunningham Falls State Park. Discover the charming town of Ellicott City, with its historic Main Street and its unique shops and restaurants. Check out the intriguing Edgar Allan Poe House and Museum in Baltimore.
  • What are the best pet friendly cottage rentals 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. The Maryland Renaissance Festival offers a unique experience, while smaller town festivals throughout the state offer a chance to interact with locals. Visiting local breweries or wineries provides opportunities for social interaction. Farmer's markets are another great place to meet Marylanders and sample local produce.
  • What are the best cottage rentals with parking in Maryland?

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

    Maryland's cuisine is heavily influenced by the Chesapeake Bay. Crab cakes are a must-try, along with steamed blue crabs. Smith Island Cake, a unique layer cake, is another local specialty. Try the Chesapeake Bay oysters, known for their unique flavor. Many restaurants offer fresh seafood dishes prepared in various ways.
  • What are some recommended items to pack for a stay in Maryland, United States?

    Pack comfortable walking shoes, especially if you plan on exploring cities on foot. Bring sunscreen and insect repellent, particularly during the warmer months. Layers of clothing are recommended, as Maryland weather can be unpredictable. If visiting during the colder months, pack warm clothing and waterproof outerwear. Don't forget swimwear if you plan on visiting the beach or swimming in the Chesapeake Bay.

Nearby regions

Best Maryland cottage rentals with jacuzzi

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

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 St. Leonard's cottage, near Long Beach, offers easy access to Flag Ponds Nature Park and Flag Harbour Marina, both within 1.6km, and is less than 1.6km from Long Beach and Matoaka Beach.
This 74 square metre holiday home sleeps five, boasting two bedrooms, two bathrooms, a fully equipped kitchen, swimming pool, jacuzzi, and terrace, plus free Wi-Fi and on-site parking.
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 spacious five-bedroom, three-bathroom holiday home in Piney Point offers direct access to a private beach on the Chesapeake Bay and features a gourmet kitchen, air conditioning, and a hot tub with bay views.
Guests can enjoy provided kayaks and paddleboards, a private deck, a top-floor balcony with expansive bay vistas, and a Tesla charging station, with accommodation for up to twelve people and pet-friendly options available.
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 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
10 160 reviews

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

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.

Best pet friendly Maryland cottage rentals

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

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 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.
Pet Friendly Water View Cottage - Maryland
10 38 reviews

Pet Friendly Water View Cottage

cottage, Riviera Beach
This charming cottage is located in Pasadena, Maryland, a picturesque waterfront neighbourhood just 20 kilometres from both Annapolis and Baltimore, offering easy access to a range of attractions. The cottage has received excellent reviews from previous guests, highlighting its comfortable and welcoming atmosphere.
The cottage spans 111 square metres and comfortably accommodates up to four guests in its two bedrooms and two bathrooms. Guests can enjoy a fully equipped kitchen, a private garden, and a host of amenities including air conditioning, laundry facilities, and free parking. The cottage is also pet-friendly, allowing guests to bring their furry companions along.
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 a charming holiday home situated just a short walk from the waterfront in Rock Hall, offering easy access to shops, restaurants, and entertainment. The cottage consistently receives excellent reviews from guests, highlighting its comfortable and convenient location.
The property features two bedrooms, accommodating up to seven guests, making it ideal for families or groups of friends. The cottage offers a range of amenities including a fully equipped kitchen, a private garden, and a patio for outdoor dining, ensuring a relaxing and enjoyable stay.
"Point Of View" Waterfront Cottage With Panoramic Views On Tilghman Island - Maryland
10 28 reviews

"Point Of View" Waterfront Cottage With Panoramic Views On Tilghman Island

cottage, Tilghman Island
This Tilghman Island holiday home is conveniently located within a 1.6km walk of Kronsberg Park and the Talbot County Library Tilghman Branch, and within a 2.4km walk of the Tilghman Watermen’s Museum and Knapp’s Narrows Marina & Inn.
This pet-friendly 60 square metre self-catering property sleeps four, boasting two bedrooms, one bathroom, a fully equipped kitchen with washing machine, free Wi-Fi, air conditioning, parking, a fireplace, and a smart TV.
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