Villas and Holiday homes in Maryland

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Maryland villas
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15306 Villa rentals in Maryland

Best Maryland villas and holiday homes with a pool

Among the 15306 accommodations in Maryland, here are the 4 best villas and holiday homes with a pool

Coastal Waterfront 1 Bedroom Cottage - Maryland
10 208 reviews
Maryland
28/06 – 29/06
SG$536/nightfor 1 night

Coastal Waterfront 1 Bedroom Cottage

1 2
house , Mayo
This waterfront cottage is located just 3.2km from the historic centre of Annapolis and the US Naval Academy, in a peaceful neighbourhood on the South River. The property has been highly rated by previous guests, with excellent scores for cleanliness, location and overall experience.
The cottage has one bedroom and one bathroom, and can comfortably sleep up to four guests. The property offers a range of amenities including a fully equipped kitchen, a patio with a grill and fire pit, and access to a swimming pool and garden, making it perfect for a relaxing getaway.
Secluded Waterfront Retreat 2 Bed 1 1/2 Baths Private Guest House W Pool & Beach - Maryland
10 22 reviews
Maryland
04/09 – 07/09
SG$612/nighttotal: SG$1836 (3 )

Secluded Waterfront Retreat 2 Bed 1 1/2 Baths Private Guest House W Pool & Beach

2 2
house , White Marsh
This White Marsh waterfront villa offers direct access to the Bird River, a private beach, and is conveniently located near White Marsh Mall and major attractions such as Johns Hopkins Hospital and the Baltimore Inner Harbour (distances unspecified).
The two-bedroom property, sleeping up to four guests, boasts a swimming pool, spa, outdoor kitchen, and kayaks/canoes for river exploration; full kitchen, Wi-Fi and air conditioning are included.
Charming Cottage With Pool Access And Wifi In Lovely Rock Hall - Maryland
10 4 reviews
Maryland
04/09 – 07/09
SG$332/nighttotal: SG$996 (3 )

Charming Cottage With Pool Access And Wifi In Lovely Rock Hall

1 2
cottage , Rock Hall
This Rock Hall cottage, ideally situated near the Waterman's Museum and The Mainstay, offers convenient access to Rock Hall Harbour and Rolph's Wharf Marina, all within walking distance (exact distances unspecified).
The 56-square-metre (approximately 600 square feet) self-catering property features a two-story layout with a king-size bedroom upstairs, a downstairs living area, and accommodates two guests; amenities include air conditioning, Wi-Fi, a mini-refrigerator, and a private pool (accessible May 1st to September 21st, 11 am to 5 pm).
Exquisite & Serene 1 Bedroom, 1 Full Bath Apartment - Maryland
9.4 14 reviews
Maryland
15/10 – 18/10
SG$237/nighttotal: SG$711 (3 )

Exquisite & Serene 1 Bedroom, 1 Full Bath Apartment

1 2
house , Brock Hall
This Brock Hall house, near Addison Road-Seat Pleasant Station (22km) and approximately 32km from both the Supreme Court and the US Capitol, offers a convenient base for exploring the area.
The 223-square-metre property boasts a private pool, garden, terrace, fitness centre, and parking, accommodating up to six guests in its one-bedroom, one-bathroom layout with a fully equipped kitchenette.

Best family friendly Maryland villas and holiday home

Among the 15306 accommodations in Maryland, here are the 4 best family friendly villas and holiday homes

Modern Retreat | Kid Playhouse | 5 Acres | Games - Maryland
10 99 reviews
Maryland
03/09 – 07/09
SG$660/nighttotal: SG$2640 (4 )

Modern Retreat | Kid Playhouse | 5 Acres | Games

1 4
cabin , Dargan
The C&O Abode is a modern, family-friendly cabin situated in the quiet countryside near Dargan, just 11km from Harpers Ferry National Historical Park and 16km from Shepherdstown. The three-bedroom, two-bathroom lodge sleeps up to eight guests and boasts a fully equipped kitchen, a dedicated kids' playhouse, a fire pit, a covered deck and a propane grill.
Chesapeake Paradise House - Waterfront Vacation Rental Home On The Maryland Chesapeake Bay - Maryland
Maryland
10/09 – 13/09
SG$1240/nighttotal: SG$3720 (3 )

Chesapeake Paradise House - Waterfront Vacation Rental Home On The Maryland Chesapeake Bay

7 7
house , Deale
This waterfront holiday home in Deale, Maryland, is located 30 kilometres from Annapolis Harbour and 38 kilometres from Baltimore/Washington International Airport.
This spacious 279 square metre property sleeps 24 guests across six bedrooms and four bathrooms, offering a fully equipped kitchen, air conditioning, a hot tub, a terrace, a garden, and private parking, with waterfront access to the Chesapeake Bay.
Luxury Family - 5br, Game Rm, Movie Rm, Fire Pit, Beach - Maryland
Maryland
03/09 – 07/09
SG$2063/nighttotal: SG$8252 (4 )

Luxury Family - 5br, Game Rm, Movie Rm, Fire Pit, Beach

5 4
house , Long Beach
This spacious 5-bedroom holiday home is located in Saint Leonard, 22.5 kilometres from New Carrollton and 20.9 kilometres from Annmarie Garden.
This substantial property boasts 372 square metres of living space, accommodating up to 25 guests with a game room, home cinema, table tennis, indoor play area, and outdoor dining, all featuring water views and free private parking.
Waterfront Cabin Home - 9+ Private Wooded Acres - Maryland
10 118 reviews
Maryland
11/07 – 16/07
SG$418/nighttotal: SG$2090 (5 )

Waterfront Cabin Home - 9+ Private Wooded Acres

1 4
cabin , Darlington
The Gunpowder Cabin is located in Northern Maryland, just 80 kilometres from Baltimore and 24 kilometres from Interstate 95, situated between Philadelphia and Baltimore. It boasts excellent user, location and cleanliness ratings, ensuring a comfortable and enjoyable stay.
This two-bedroom, one-bathroom cabin can accommodate up to four guests. Guests can enjoy a range of amenities, including a fully equipped kitchen, air conditioning, a garden, parking, internet access and a secluded setting on nine wooded acres with riverfront access, hiking trails and outdoor amenities.

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

Riverside House W/ Kayaks, Piano & Fireplace - Maryland
9.0 3 reviews
Maryland
27/06 – 04/07
SG$576/nighttotal: SG$4032 (7 )

Riverside House W/ Kayaks, Piano & Fireplace

5 2
house , California
This California beachfront property, situated 2.9 kilometres from the Calvert Marine Museum and 40 kilometres from New Carrollton, offers stunning sea views and easy access to local attractions.
This five-bedroom house boasts 214 square metres of floor space, sleeps up to 17 guests, and includes amenities such as free Wi-Fi, kayaks, bicycles, and a fully equipped kitchen; a piano provides added entertainment.
Spacious Home W/ Tranquil Patio ~ 29 Mi To Dc! - Maryland
9.7 3 reviews
Maryland
16/08 – 23/08
SG$835/nighttotal: SG$5845 (7 )

Spacious Home W/ Tranquil Patio ~ 29 Mi To Dc!

5 2
house , Severn
This spacious Severn house, located approximately 6 kilometres from Baltimore-Washington International Thurgood Marshall Airport and 24 kilometres from various Baltimore attractions including Carroll Park and the Inner Harbour, offers convenient access to major landmarks. This five-bedroom, three-bathroom property boasts a 279 square metre floor area, sleeps 23 guests, and includes a fully equipped kitchen, garden, parking, and free Wi-Fi.
Cozy, Modern Townhome By Mimi And Sandrine - Maryland
Maryland
27/06 – 13/07
SG$327/nighttotal: SG$5232 (16 )

Cozy, Modern Townhome By Mimi And Sandrine

1 5
house , Waldorf
This modern townhome in Waldorf is situated 26 kilometres from National Harbour and 31 kilometres from Alexandria's Christ Church.
This spacious 93 square metre residence accommodates up to eleven guests, offering a fully equipped kitchen, complimentary Wi-Fi, private parking, and entertainment facilities including billiards and table tennis.
Lock Keepers Cottage On C&o Canal/potomac River - Maryland
9.9 232 reviews
Maryland
03/09 – 07/09
SG$242/nighttotal: SG$968 (4 )

Lock Keepers Cottage On C&o Canal/potomac River

3 4
house , Mercersville
Lock Keepers Cottage, situated in Sharpsburg, Maryland, offers a tranquil escape near the C&O Canal and Potomac River, approximately 40 kilometres from Harpers Ferry National Historical Park and the Appalachian Trail Conference Headquarters.
This three-bedroom property, boasting 104 square metres of floor space, provides a fully equipped kitchen, terrace, garden, free Wi-Fi, and private parking; nearby recreational activities include skiing and cycling.

Best Maryland villas and holiday homes with jacuzzi

Hidden Treasure - Maryland
8.7 44 reviews
Maryland
15/10 – 18/10
SG$528/nighttotal: SG$1584 (3 )

Hidden Treasure

4 6
house , Oakland
Hidden Treasure is a 4-bedroom house in Oakland, Maryland, just a short drive from popular skiing and cycling destinations. It has received very good user ratings, and excellent location and cleanliness ratings.
This spacious property is 81 square metres and comes equipped with a fully equipped kitchen, a washing machine, free Wi-Fi, a patio, private parking, and a jacuzzi. Enjoy the fresh air and stunning scenery of the surrounding mountains, or take advantage of the nearby skiing and cycling opportunities.
Bankors Aweigh - Maryland
Maryland
10/09 – 13/09
SG$1470/nighttotal: SG$4410 (3 )

Bankors Aweigh

1 7
house , Tilghman Island
This Tilghman Island holiday home is located 21 kilometres from the Academy Of The Arts in Mount Pleasant and 101 kilometres from Baltimore-Washington International Airport.
This detached property offers accommodation for up to 15 guests across four bedrooms, featuring a private swimming pool, hot tub, Wi-Fi, parking, and a fully equipped kitchen.
House ∙ 3 Bedrooms ∙ 8 Guests - Maryland
Maryland
25/06 – 08/08
SG$1091/nighttotal: SG$48004 (44 )

House ∙ 3 Bedrooms ∙ 8 Guests

3 3
house , Deer Park
Treeline Lodge, a historic cabin, is located in a prime Deep Creek spot, a 300-meter walk to Honi-Honi Bar and minutes from Deep Creek Lake, dining, and year-round activities.
This pet-friendly lodge accommodates up to 8 guests and features 3 bedrooms, 3 bathrooms, air conditioning, a swimming pool, Jacuzzi, a garden, parking, a large deck with lake views, a tiki bar, a hammock, an outdoor shower, and a fire pit.
Live A Little - Maryland
9.5 25 reviews
Maryland
15/10 – 18/10
SG$438/nighttotal: SG$1314 (3 )

Live A Little

3 6
house , Accident
This spacious apartment near McHenry, approximately 64 kilometres from Morgantown Municipal Airport, provides easy access to nearby skiing in McHenry.
The 164 square metre property sleeps six comfortably, boasting three bedrooms, four bathrooms, a fully equipped kitchen with dishwasher and microwave, in-unit laundry, a fireplace, cable TV, Wi-Fi, parking, a jacuzzi, and a terrace/balcony with garden access.
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