Villas and Holiday homes in Maryland

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Maryland villas
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20050 Villa rentals in Maryland

Best Maryland villas and holiday homes with a pool

Among the 20050 accommodations in Maryland, here are the 4 best villas and holiday homes with a pool

Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels - Maryland
9.6 138 reviews

Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels

cottage, Easton
This charming cottage is located in St. Michaels, a short walk from the St. Michaels Museum, Chesapeake Bay Maritime Museum, and St. Michaels Winery. It boasts excellent user ratings, making it a popular choice for travellers.
The property offers 130 square metres of space, with two bedrooms and three bathrooms, comfortably accommodating up to five guests. The cottage comes equipped with a fully fitted kitchen, a private patio, a fireplace, and a garden, perfect for relaxing and enjoying the outdoors.
Chesapeake Waterfront - 7br 5ba - Beach Pool Dock - Maryland
No reviews

Chesapeake Waterfront - 7br 5ba - Beach Pool Dock

house, Madison
This Chesapeake Bay waterfront property, situated in Woolford, Maryland, is 43km from the Academy of the Arts and 77km from Salisbury-Ocean City Wicomico Regional Airport.
This seven-bedroom, five-bathroom house boasts 374 square metres of floor space, a private pool and dock, accommodating up to 25 guests and offering amenities including a fully equipped kitchen, Wi-Fi, and a fireplace.
Blake House Historic Estate With Private Inn - Maryland
10 2 reviews

Blake House Historic Estate With Private Inn

house, Centreville
Blake House Historic Estate, a six-bedroom villa in Centreville, Maryland, is situated 34km from the Academy of the Arts and 39km from Sandy Point State Park.
This 465-square-metre property offers ample space for up to 20 guests, boasting a private pool, fitness centre, fully equipped kitchen, and laundry facilities.
Baydream Believer - Maryland
10 1 review

Baydream Believer

house, Tilghman Island
Baydream Believer, a five-bedroom house in Saint Michaels, Maryland, is situated approximately 24 kilometres from the Academy of the Arts and 106 kilometres from Salisbury-Ocean City Wicomico Regional Airport, offering convenient access to Tilghman Island.
This 465-square-metre property sleeps up to 15 guests and boasts a private pool, Jacuzzi, tennis court, and fully equipped kitchen; additional features include a terrace, garden, and free Wi-Fi.

Best family friendly Maryland villas and holiday home

Among the 20050 accommodations in Maryland, here are the 4 best family friendly villas and holiday homes

Spacious Federal Hill Home With Rooftop & 4 Parking Spots - Maryland
9.7 13 reviews

Spacious Federal Hill Home With Rooftop & 4 Parking Spots

house, Baltimore
This luxurious Federal Hill residence is situated 1.8 kilometres from Baltimore's Inner Harbour, providing easy access to attractions such as the Historic Ships in Baltimore and the Baltimore Convention Center.
This spacious property boasts 251 square metres of living space, featuring four bedrooms, five bathrooms, and ample amenities including a fitness centre, tennis court, and parking for four vehicles, comfortably accommodating up to 25 guests.
Relish In Rockville Rambler - Maryland
10 2 reviews

Relish In Rockville Rambler

house, Washington Grove
This Rockville Rambler is located in Rockville, approximately 30.5 kilometres from the Phillips Collection and 32.2 kilometres from the White House.
This spacious 44 square metre dwelling offers accommodation for up to 19 guests, featuring four bedrooms, three bathrooms, a well-equipped kitchen with a dishwasher, and complimentary WiFi, with on-site staff available for airport transfers.
Historic Downtown 3br Crabby Patty-∙walk To Usna - Maryland
No reviews

Historic Downtown 3br Crabby Patty-∙walk To Usna

house, Annapolis
This detached house offers a prime downtown Annapolis location, just a short walk from the US Naval Academy and the city waterfront.
This family-friendly property accommodates up to eight guests across three bedrooms and two-and-a-half bathrooms, featuring a fully equipped kitchen, air conditioning, parking, and in-home laundry facilities.
Luxurious 4br, Private Pool, Heated Spa-open Year-round, Near Downtown! - Maryland
10 159 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.

Frequently asked questions about villa rentals in Maryland

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

    Maryland offers a diverse range of attractions. For history buffs, a visit to Annapolis, the state capital, with its historic district and the United States Naval Academy is a must. Baltimore boasts the Inner Harbour, Fort McHenry (where the Star-Spangled Banner was written), and the American Visionary Art Museum. Nature lovers should explore Assateague Island National Seashore, known for its wild horses, or the Chesapeake Bay, offering opportunities for boating, fishing, and birdwatching. The charming town of St. Michaels on the Eastern Shore is also a popular destination.
  • What are the best villa rentals in Maryland?

  • Is Maryland, United States known for mountains, beaches, forests, or other types of landscapes?

    Maryland's landscape is surprisingly varied. While not known for towering mountains, it does have rolling hills in western Maryland, particularly in the Appalachian Mountains region. The Chesapeake Bay dominates the eastern portion of the state, providing extensive shoreline and numerous waterways. There are also beautiful beaches on the Atlantic coast, and extensive forests throughout the state, particularly in the western counties.
  • What are the best villa rentals with a pool in Maryland?

  • What are the most surprising and hidden attractions in Maryland, United States?

    Many people overlook the Eastern Neck National Wildlife Refuge, a beautiful area for birdwatching and nature walks. The Catoctin Mountain Park, with its hiking trails and Cunningham Falls, offers stunning scenery. For a unique experience, visit the Havre de Grace Decoy Museum, showcasing the artistry of duck decoys. The Washington County Museum of Fine Arts also frequently hosts lesser-known but impressive exhibitions.
  • What are the best villa rentals with a jacuzzi in Maryland?

  • What are some unique ways to learn about the culture of Maryland, United States by engaging with its people?

    Attend a local festival like the Maryland Renaissance Festival for a taste of history and community spirit. Visit a Chesapeake Bay crab house and chat with the locals about their way of life. Explore the many farmers' markets across the state, talking to the producers about their produce and methods. Consider taking a guided walking tour of a historic district in a city like Annapolis or Baltimore, interacting with the guides and other participants.
  • What are the best villa rentals for families and kids in Maryland?

  • How much time should you set aside to thoroughly explore Maryland, United States?

    A week would allow for a good overview of Maryland's highlights, but to truly explore its diverse regions and attractions, two weeks or even more would be ideal. It depends on your interests; someone focused solely on the Chesapeake Bay might need less time than someone who wants to explore both the mountains and the coast.
  • What are the best pet friendly villa rentals in Maryland?

  • Is there anything you might not think to pack for Maryland, United States?

    Depending on the time of year, insect repellent is a good idea, especially if you plan on spending time outdoors, particularly near the Chesapeake Bay. Comfortable walking shoes are essential for exploring the many historic towns and natural areas. If visiting during the summer months, pack light clothing and sunscreen, while layers are recommended for spring and autumn.
  • What are the best villa rentals with parking in Maryland?

  • What cultural experiences or workshops in Maryland, United States offer something different?

    The Maryland Historical Society in Baltimore offers various workshops and events related to Maryland history. Many art museums across the state offer classes and workshops. Several locations in the Chesapeake Bay area offer oyster shucking workshops or crabbing lessons, providing a unique hands-on cultural experience.
  • Are there any food festivals in Maryland, United States where you can try local food?

    The Maryland Seafood Festival is a large event celebrating the state's seafood. Many smaller towns and cities hold their own festivals throughout the year, often featuring local produce and dishes. The Great Frederick Fair includes a wide variety of food options.
  • What seasonal natural events, such as migrations or blooming periods, occur in Maryland, United States?

    Spring brings the blooming of wildflowers, particularly in the western mountains and along the Chesapeake Bay. Autumn showcases vibrant fall foliage in the western counties. Bird migration is significant throughout the year, with peak seasons in spring and autumn, particularly visible in areas like the Eastern Neck National Wildlife Refuge and Assateague Island.
  • What exclusive experiences are available when visiting Maryland, United States?

    Private boat tours of the Chesapeake Bay offer a unique perspective. Guided kayaking or canoeing trips through the waterways provide a closer look at the natural environment. A private tour of the United States Naval Academy in Annapolis or a behind-the-scenes tour of a historic home can also be arranged.

Nearby regions

Best Maryland villas and holiday homes with a kitchen

Auth Townhome - Maryland
No reviews

Auth Townhome

house, Camp Springs
This Auth Townhome in Camp Springs is located 12.07 kilometres from Addison Road-Seat Pleasant and 12.87 kilometres from National Harbour, providing convenient access to several key attractions.
This 1000 square metre residence offers a fully equipped kitchen, air conditioning, and complimentary private parking and free WiFi for up to 11 guests, with a strict no-bachelor(ette) policy, and is situated 13.04 kilometres from the U.S. Capitol, Nationals Park and the Supreme Court.
Michele Palace - Maryland
8.8 12 reviews

Michele Palace

house, Summerfield
Michele Palace, a three-bedroom house in Hyattsville, Maryland, is conveniently located approximately 15 kilometres from major Washington, D.C. landmarks such as the Supreme Court and the Capitol Building.
This Summerfield property sleeps up to 15 guests, offering free Wi-Fi, private parking, a fully equipped kitchen with dishwasher, and is close to Addison Road-Seat Pleasant station (4 km).
Blake House Historic Estate With Private Inn - Maryland
10 85 reviews

Blake House Historic Estate With Private Inn

house, Centreville
This historic Maryland estate, Blake House and Crown and Anchor Inn, is situated in Centreville, offering direct water access and 12 acres of manicured gardens, with proximity to Centreville's attractions (distances to specific landmarks would need to be specified).
This 465 square metre (465m²) property boasts six bedrooms, six bathrooms, and sleeps twelve guests, featuring a pool, extensive gardens, a private pier, a boat lift, and recreational facilities including a bar, billiards, and foosball in the Crown and Anchor Inn.
Tranquil Trio 6 Br, 4 Ba, 3 Units, Deer Haven - Maryland
No reviews

Tranquil Trio 6 Br, 4 Ba, 3 Units, Deer Haven

house, Fairland
This six-bedroom, four-bathroom house in Silver Spring, Maryland, approximately 24-27 kilometres from Washington, D.C. attractions such as the White House and National Mall, offers ample space for large groups.
The 930 square metre property features three separate units, a fully equipped kitchen, a garden, free Wi-Fi, and a fireplace; it comfortably accommodates up to 29 guests.

Best Maryland villas and holiday homes with jacuzzi

Washington's Retreat - Maryland
No reviews

Washington's Retreat

house, Deale
This custom-built property in Tracy's Landing offers direct bay views and semi-private beach access, located 37 kilometres from Annapolis, 55 kilometres from Washington D.C., and 79 kilometres from Baltimore.
This family-friendly holiday home accommodates up to 14 guests with five bedrooms and five bathrooms, featuring a heated swimming pool, year-round hot tub, extensive games room, and a four-season screened porch, with kayaks provided for bay enjoyment between May and November.
Cozy Waterfront Cabin Escape - Maryland
10 55 reviews

Cozy Waterfront Cabin Escape

cabin, Middle River
This charming cabin sits on Seneca Creek in Middle River, just 20 kilometres from Baltimore City, offering a peaceful escape from the hustle and bustle. The cabin is located in a tranquil setting, perfect for those seeking a relaxing getaway.
This cosy retreat has two bedrooms and can accommodate up to four guests. The cabin comes equipped with a range of modern amenities, including high-speed internet, a hot tub, and a floating dock for kayaking, making it ideal for both work and leisure.
Coastal Edgewater Home W/ Private Hot Tub! - Maryland
No reviews

Coastal Edgewater Home W/ Private Hot Tub!

house, Mayo
This spacious Mayo holiday home is located 35km from Annapolis Harbour and 40km from Baltimore-Washington International Thurgood Marshall Airport.
The 218 square metre property boasts five bedrooms sleeping up to 17 guests, a fully equipped kitchen with dishwasher, air conditioning, a jacuzzi, free Wi-Fi, and parking; nearby attractions include Annapolis Harbour for water activities.
Firefly Cottage At The Cape, Hot Tub, Community Beach, Boat Show, Usna Football. - Maryland
10 120 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.
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