Cottages in Maryland at the best prices

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Maryland cottages
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1669 Best cottages in Maryland

Best family friendly Maryland cottage rentals

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

Relaxing, Peaceful House In Calvert County, Md Close To Beach Towns And Dc. - Maryland
10 51 reviews
Maryland
11/08 – 21/08
$303/nighttotal: $3030 (10 )

Relaxing, Peaceful House In Calvert County, Md Close To Beach Towns And Dc.

2 2
cottage , Dunkirk
This charming cottage is situated just a short distance from Fridays Creek Winery and the Patuxent River, offering a peaceful escape in the heart of Dunkirk, Maryland. It has received excellent reviews from previous guests, making it a popular choice for travellers seeking a relaxing getaway.
The cottage spans 84 square metres and comfortably accommodates up to four guests in its two bedrooms and one bathroom. Guests can enjoy a range of amenities, including a private outdoor pool, barbecue grills, and a spacious garden, as well as the convenience of a fully equipped kitchen, free Wi-Fi and a private patio.
Close To Everything Dcl, Fun For The Whole Family - Maryland
9.8 37 reviews
Maryland
14/12 – 17/12
$437/nighttotal: $1311 (3 )

Close To Everything Dcl, Fun For The Whole Family

3 5
cottage , Deer Park
This three-bedroom, three-bathroom holiday home in the Paradise Heights area of Deep Creek Lake is a short drive (approximately 2-3km) from Wisp Resort and offers easy access to Silver Tree Marine for watercraft rentals and Maryland state parks.
Sleeping up to eight guests, the property boasts a spacious layout with a large deck, gas grill, fire pit, retro arcade games, and includes a Maryland State Park pass; it is also within walking distance of Dutch's.
Serene Spot, West River Dock, Sunsets, The Bay, Only 40 Min From Alexandria, Dc. - Maryland
9.6 49 reviews
Maryland
11/08 – 21/08
$249/nighttotal: $2490 (10 )

Serene Spot, West River Dock, Sunsets, The Bay, Only 40 Min From Alexandria, Dc.

1 2
cottage , Shady Side
This waterfront cottage in Shady Side, Maryland, is situated on a peninsula on the West River, approximately 32 kilometres from Annapolis and close to Galesville.
The one-bedroom, one-bathroom property sleeps three, offering a private dock, kitchen with fridge and microwave, air conditioning, a terrace, garden, parking, internet access, and proximity to Thanksgiving Farm Wines and South River Golf Links.
"Serenity"-st. Patrick's Creek W/ Private Pier - Maryland
10 2 reviews
Maryland
17/07 – 20/07
$650/nighttotal: $1950 (3 )

"Serenity"-st. Patrick's Creek W/ Private Pier

4 2
cottage , Cobb Island
This family-friendly four-bedroom holiday home is located in Avenue, Maryland, approximately 10km from Saint Clement's Island State Park, Port Sunlight Beach, and the Saint Clements Island-Potomac River Museum.
The 182 square metre property boasts four bathrooms, a fully equipped kitchen including a dishwasher, free Wi-Fi, a terrace, and parking, comfortably accommodating eight guests and offering easy access to local attractions such as The Shoppes at McIntosh and Port of Leonardtown Winery (within 19km).

Best Maryland cottages with a garden

Rodo Beach Cottage - Dog Friendly Private Beach With Pier - Tesla Charger - Maryland
9.9 68 reviews
Maryland
22/06 – 25/06
$1054/nighttotal: $3162 (3 )

Rodo Beach Cottage - Dog Friendly Private Beach With Pier - Tesla Charger

3 4
cottage , Piney Point
This charming cottage is located in Piney Point, Maryland, just a short distance from the Chesapeake Bay. It benefits from excellent user, location and cleanliness ratings.
The cottage has three bedrooms, accommodating up to eight guests, and offers a range of amenities, including private beach access, a fishing pier, kayaks and stand-up paddle boards, a Tesla charger, and contactless check-in.
Waterfront Cottage For Paddle Boarding, Kayaking, Crabbing, And Fishing - Maryland
9.8 155 reviews
Maryland
20/07 – 23/07
$363/nighttotal: $1089 (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.
Pet Friendly Delightful Waterfront Cottage On Hoopers Island, Md. - Maryland
10 51 reviews
Maryland
22/06 – 25/06
$431/nighttotal: $1293 (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.
Premier St. Michaels Cottage - T. Blades House -  Walk To Everything In Town - Maryland
9.6 285 reviews
Maryland
22/06 – 25/06
$595/nighttotal: $1785 (3 )

Premier St. Michaels Cottage - T. Blades House - Walk To Everything In Town

2 4
cottage , Easton
This charming cottage is located in St. Michaels, a short walk from the Chesapeake Bay Maritime Museum, St. Michaels Museum, and St. Michaels Winery, making it ideal for exploring this historic town. The cottage has received excellent ratings for its location, cleanliness and overall experience.
The cottage has two bedrooms and can accommodate up to five guests, making it perfect for families or groups of friends. Guests can enjoy a range of amenities including a swimming pool, terrace, garden, and a fully equipped kitchen.

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

Firefly Cottage At The Cape, Community Beach, Spring  Adventures, Hot Tub, Usna - Maryland
10 108 reviews
Maryland
20/07 – 23/07
$497/nighttotal: $1491 (3 )

Firefly Cottage At The Cape, Community Beach, Spring Adventures, Hot Tub, Usna

1 4
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.
Hays Beach House - Hot Tub - Private Beach - Maryland
9.8 16 reviews
Maryland
17/07 – 24/07
$1511/nighttotal: $10577 (7 )

Hays Beach House - Hot Tub - Private Beach

5 5
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.
Cottage On The Bay - Maryland
8.8 3 reviews
Maryland
11/07 – 16/07
$341/nighttotal: $1705 (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.
New! Private Luxury Spa Hot Tub Retreat With Ping Pong - Maryland
10 1 review
Maryland
04/09 – 07/09
$2164/nighttotal: $6492 (3 )

New! Private Luxury Spa Hot Tub Retreat With Ping Pong

3 2
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.

Best pet friendly Maryland cottage rentals

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

Charming 1br Cottage W/ Wifi, Ac In Wonderful Wye Mills - Maryland
9.2 7 reviews
Maryland
11/08 – 21/08
$169/nighttotal: $1690 (10 )

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

2 2
cottage , Queenstown
This Queenstown cottage, near the Avalon Theatre and Third Haven Friends Meeting House, offers a convenient base for exploring local attractions such as the Hazel Miner Monument and Adkins Arboretum, although precise distances are unavailable.
The self-catering property features two bedrooms, one bathroom, sleeps four guests, and includes amenities such as Wi-Fi, air conditioning, parking, and a garden with a terrace; a washing machine and a kitchen with a fridge and microwave are also provided.
Waterfront River Cottage For 2, Dog-friendly - Maryland
9.6 27 reviews
Maryland
26/06 – 29/06
$689/nighttotal: $2067 (3 )

Waterfront River Cottage For 2, Dog-friendly

1 2
cottage , Severna Park
This charming beachside cottage is located near Severna Park, just nine miles from the B&A Trail, Severna Park Golf Center, and Bay Hills Golf Club. It has received excellent ratings for its location, cleanliness, and overall user experience.
The cottage has one bedroom and one bathroom, offering comfortable accommodation for up to two guests, and it comes equipped with a fully equipped kitchen, a terrace, a garden, a spa, and parking. Enjoy the fresh air and sunshine with the relaxing outdoor space, cook up a meal on the charcoal grill, and take advantage of the arcade/game room for entertainment.
Watrfnt Cottage @Chesapeakeparadise Kayaks/dogs Ok - Maryland
9.7 275 reviews
Maryland
13/07 – 18/07
$774/nighttotal: $3870 (5 )

Watrfnt Cottage @Chesapeakeparadise Kayaks/dogs Ok

3 8
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.
Charming Farm Cottage - Maryland
Maryland
11/08 – 21/08
$216/nighttotal: $2160 (10 )

Charming Farm Cottage

2 2
cottage , Jarrettsville
This rural holiday let in Jarrettsville is situated near cultural sites such as Monkton Railroad Station and Harford Artists Gallery, and attractions including Ladew Topiary Gardens and Liriodendron Mansion, offering an exceptional stay experience.
This two-bedroom, non-smoking cottage accommodates up to six guests, features on-site laundry facilities, and is conveniently located for access to family-friendly entertainment like Maize Quest Fun Park and Guppy Gulch Quarry.
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