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

Ski Harbor 45 - Maryland
8.5 60 reviews

Ski Harbor 45

house, Accident
This apartment is located in McHenry, just 2km from attractions like Funland, Deep Creek Lake, and Wisp Resort. It has received very good user ratings, and the location and cleanliness have been rated excellent.
The apartment has 2 bedrooms and covers 104 square metres. It has a range of amenities including a swimming pool, jacuzzi, garden, sauna, tennis court, and parking, as well as a fully equipped kitchen and a fireplace.
Pets Welcome: Quiet Silver Spring Retreat! - Maryland
No reviews

Pets Welcome: Quiet Silver Spring Retreat!

house, Ashton-Sandy Spring
This three-bedroom house in Fulton, Ashton-Sandy Spring, offers a peaceful retreat approximately 27-31 kilometres from Washington, D.C. attractions including the White House and the Phillips Collection.
The 121 square metre property sleeps up to 11 guests and boasts a fully equipped kitchen, private swimming pool, garden, parking, and free Wi-Fi; in-unit laundry facilities are also provided.
Cabin ∙ 5 Bedrooms ∙ 10 Guests - Maryland
10 6 reviews

Cabin ∙ 5 Bedrooms ∙ 10 Guests

cabin, Oakland
"A Helluva View" is a spacious four-bedroom lodge located in the Deep Creek Lake area, approximately 160 kilometres from Oakland, offering stunning mountain views and access to a range of outdoor activities.
This luxurious cabin features a private deck with a hot tub, a fully equipped kitchen, and a fire pit, perfect for relaxing and enjoying the serene surroundings.
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.

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

143 M² House ∙ 2 Bedrooms ∙ 8 Guests - Maryland
9.3 5 reviews

143 M² House ∙ 2 Bedrooms ∙ 8 Guests

house, Accident
This ski-in, ski-out townhome in the Villages of the Wisp community offers direct access to Wisp Resort and is a short drive to Lodestone Golf Course, The Whitewater Course, Funland, and local amenities.
This 142 square meter holiday cottage accommodates up to 8 guests across 2 bedrooms and 3 bathrooms, featuring a fully equipped kitchen, open-plan living area with a fireplace, Smart TVs, and balconies with mountain or garden views, with a 4WD vehicle recommended during winter months.
The Pines - Maryland
8.7 30 reviews

The Pines

house, Swanton
The Pines is located in Swanton, Maryland, just a short drive from popular skiing and cycling destinations. It has received excellent ratings for its location, cleanliness and overall experience.
The holiday home is spacious, offering 120 square metres of living space and three bedrooms. Guests can enjoy a private patio, free parking, free Wi-Fi, a fully equipped kitchen and a comfortable living area with a satellite TV.
Glen Burnie Vacation Rental W/ Private Deck! - Maryland
No reviews

Glen Burnie Vacation Rental W/ Private Deck!

house, Riviera Beach
Vacation house rental. You will stay in Riviera Beach.
Facilities and services: free parking, a fridge and a kitchen. This house is very convenient for families.
5 Mi To Inner Harbor: Expansive Family Getaway - Maryland
No reviews

5 Mi To Inner Harbor: Expansive Family Getaway

house, Baltimore
House. You will be in Baltimore.
Facilities and services include an iron, free parking and a washing machine. This house is very convenient for families.

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

Secluded Cozy Cottage In Historic Downtown - Maryland
9.6 22 reviews

Secluded Cozy Cottage In Historic Downtown

cottage, Annapolis
This charming cottage is located in Annapolis' Historic District, just a short walk from the City Dock and within easy reach of the State House and other key landmarks. The cottage is situated in a quiet neighbourhood, offering a peaceful retreat from the bustling city centre.
The cottage is a spacious two-bedroom property that can comfortably accommodate up to eight guests. It features a modern kitchen, a private patio with a BBQ, and a comfortable living area with an electric fireplace, a 55" Roku TV, and a full daybed.
138 M² House ∙ 3 Bedrooms ∙ 5 Guests - Maryland
No reviews

138 M² House ∙ 3 Bedrooms ∙ 5 Guests

house, N. Bethesda
House listing for 5 guests. You will be based in N. Bethesda.
Facilities and services include a washing machine, a terrace and a dish washer.
Little Lodge - Maryland
9.9 524 reviews

Little Lodge

cabin, Boonsboro
This charming holiday home is located in the mountains near Boonsboro, just a 15-minute walk from three state parks, perfect for exploring nature. It has consistently received excellent ratings for location, cleanliness, and overall guest satisfaction.
The property offers two bedrooms and one bathroom, comfortably accommodating up to five guests. You'll enjoy a fully equipped kitchen, a cosy fireplace, a terrace, and a garden, perfect for relaxing and enjoying the beautiful surroundings.
Riverdale Retreat Spacious 4br Dc Access - Maryland
No reviews

Riverdale Retreat Spacious 4br Dc Access

house, Riverdale Park
Riverdale Retreat, a detached house in Springbrook Terrace, is located between 11.6 and 13.8 kilometres from the U.S. Capitol and Washington Union Station.
This spacious 183 square metre dwelling offers four bedrooms, accommodating up to 15 guests, with a fully equipped kitchen featuring a fridge, microwave, and dishwasher, plus air conditioning and garden access for your convenience.

Best Maryland villas and holiday homes with jacuzzi

Idyllic Pasadena Retreat With Garden + Hot Tub! - Maryland
No reviews

Idyllic Pasadena Retreat With Garden + Hot Tub!

house, Lake Shore
House rental listing. You will be based in Lake Shore.
Facilities and services include a fridge, a washing machine and free parking. You can also relax in the jacuzzi!
Home Sweet Cabin - Maryland
8.6 72 reviews

Home Sweet Cabin

cabin, Oakland
Home Sweet Cabin is situated in Oakland, Maryland, within easy reach of skiing and cycling opportunities. The property has received excellent ratings for location and cleanliness, and very good ratings for user experience.
This 4-bedroom holiday home is 130 square metres in size. The cabin offers a range of amenities, including a fully equipped kitchen, a terrace, a garden, a jacuzzi, free parking, and a tennis court.
Oasis By The Bay - Waterfront Heated Pool Hot Tub - Maryland
10 3 reviews

Oasis By The Bay - Waterfront Heated Pool Hot Tub

house, Highland Beach
This six-bedroom Annapolis waterfront property enjoys a private location, 0.3 km from Bay Ridge Beach and 7.7 km from Annapolis Harbour, offering easy access to both.
This Highland Beach house boasts 520 square metres of space, sleeping up to 23 guests and including a heated pool, Jacuzzi, sauna, and spa, plus a fully equipped kitchen and free Wi-Fi.
Modern Townhome  Baltimore/annapolis - Maryland
10 8 reviews

Modern Townhome Baltimore/annapolis

house, Severn
This spacious 3200 sq ft (approx. 297 sq m) four-storey townhouse in Hanover, Maryland, offers convenient access to Arundel Mills shopping mall, Annapolis (approximately 30 km away), and Fort Meade.
The property boasts three bedrooms, three bathrooms, sleeping arrangements for six guests, a hot tub, multiple decks, and is within 50 km of horseback riding trails.
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