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

Spectacular Oceanfront Penthouse - Unit 1203 - Maryland
9.0 5 reviews
Maryland
14/12 – 17/12
SG$318/nighttotal: SG$954 (3 )

Spectacular Oceanfront Penthouse - Unit 1203

2 5
house , Ocean City
Ocean City's Unit 1203, a beachfront penthouse, offers direct beach access, is a 0.6km walk from Ocean City Beach, 2.4km from Northside Park, and within 6.4km of Thunder Lagoon Waterpark and the Roland E. Powell Convention Centre.
This 98 square metre, two-bedroom, two-bathroom apartment sleeps up to 15 guests and boasts a fully equipped kitchen, private patio, indoor pool, elevator access, free Wi-Fi, and parking; enjoy breathtaking sea views from this luxurious dwelling.
Bayberry Cove - Maryland
Maryland
01/09 – 30/11
SG$1820/nighttotal: SG$163800 (90 )

Bayberry Cove

1 2
house , Madison
This property is located in Woolford, 37 kilometres from the Academy Of The Arts and 43 kilometres from Federalsburg Marina.
This 630 square metre residence accommodates up to 33 guests across 8 bedrooms and 7 bathrooms, featuring a fully equipped kitchen, private swimming pool, complimentary WiFi, and on-site parking.
Wye Topia - Maryland
Maryland
03/09 – 07/09
SG$1633/nighttotal: SG$6532 (4 )

Wye Topia

1 4
house , Queenstown
This Queenstown property, situated in Grasonville, Maryland, is conveniently located approximately 42km from Annapolis Harbour and 29km from Sandy Point State Park.
This spacious 340 square metre house boasts four bedrooms, four bathrooms, a private swimming pool, free Wi-Fi, parking, and a fully equipped kitchen, comfortably accommodating up to 21 guests.
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.

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

Private Beach Front Getaway At The Sunshine Beach Cottage. - Maryland
9.8 80 reviews
Maryland
03/09 – 07/09
SG$699/nighttotal: SG$2796 (4 )

Private Beach Front Getaway At The Sunshine Beach Cottage.

3 4
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.
Updated North Beach Cottage: Pet Friendly! - Maryland
9.6 72 reviews
Maryland
20/07 – 23/07
SG$489/nighttotal: SG$1467 (3 )

Updated North Beach Cottage: Pet Friendly!

3 4
house , North Beach
This North Beach cottage is located in Deale, Maryland, just 43 kilometres from Annapolis Harbour and 43 kilometres from Addison Road-Seat Pleasant. The property has received excellent ratings for its cleanliness, location, and overall user experience.
The cottage offers 3 bedrooms and 2 bathrooms across 134 square metres, comfortably accommodating up to 8 guests. The property is pet-friendly, air-conditioned, and includes a swimming pool, spa, garden, parking, a fully equipped kitchen, washing machine, Wi-Fi, cable TV, and a patio.
Luxurious National Harbour Home - Maryland
10 1 review
Maryland
17/07 – 24/07
SG$586/nighttotal: SG$4102 (7 )

Luxurious National Harbour Home

4 5
house , Glassmanor
This luxurious detached house in Oxon Hill is located 6.1 kilometres from National Harbor and within 9.3 kilometres of historic Alexandria attractions including Christ Church, Stabler-Leadbeater Apothecary Museum, and Gadsby's Tavern Museum.
This spacious 223 square metre air-conditioned accommodation sleeps 19 guests across 4 bedrooms and 2 bathrooms, offering a fully equipped kitchen with a dishwasher, a pool table, table tennis, and complimentary private parking.
Beautiful Remodeled Downtown Frederick Cottage (Pet-friendly) - Maryland
9.9 283 reviews
Maryland
28/06 – 29/06
SG$448/nightfor 1 night

Beautiful Remodeled Downtown Frederick Cottage (Pet-friendly)

3 2
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.

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

302 M² House ∙ 3 Bedrooms ∙ 6 Guests - Maryland
Maryland
07/07 – 07/08
SG$197/nighttotal: SG$6107 (31 )

302 M² House ∙ 3 Bedrooms ∙ 6 Guests

3 4
house , Urbana
House rental for up to 6 people. Your accommodation will be located in Urbana.
Facilities and services include a fridge, a freeze and a kitchen.
Beautiful 1br Walkout Fenced & Gated Villa, Onsite Parking, Pet Friendly-2+acres - Maryland
8.7 39 reviews
Maryland
26/06 – 29/06
SG$340/nighttotal: SG$1020 (3 )

Beautiful 1br Walkout Fenced & Gated Villa, Onsite Parking, Pet Friendly-2+acres

1 2
house , Darnestown
This family-friendly villa is located in Germantown, just 1.6 kilometres from Seneca Creek State Park and the Chesapeake and Ohio Canal National Historic Park, offering a tranquil setting close to nature. Guests have consistently rated this property as very good, highlighting its comfortable and well-equipped nature.
The villa provides ample space for families or groups, featuring a modern kitchen, a relaxing garden, and a patio for outdoor enjoyment. Guests can enjoy a range of amenities, including a swimming pool, a jacuzzi, a tennis court, and a spa, ensuring a relaxing and enjoyable stay.
The Cottage At Merryland Farm - Maryland
10 6 reviews
Maryland
04/09 – 07/09
SG$311/nighttotal: SG$933 (3 )

The Cottage At Merryland Farm

1 2
cottage , Kingsville
This self-catering cottage, situated in Hydes, Baltimore County, Maryland, offers a rural retreat approximately 24km from Kingsville, close to Oregon Ridge Nature Center and Greencroft Open Space.
The 74 square metre property, sleeping up to three guests, features a bedroom, bathroom, kitchen with fridge and microwave, air conditioning, garden, parking, internet access, and allows well-behaved dogs (with prior approval and fee); additional bedrooms are available in the main house.
Private Single Family Home Close To Both Water And Downtown! - Maryland
9.7 90 reviews
Maryland
07/07 – 07/08
SG$513/nighttotal: SG$15903 (31 )

Private Single Family Home Close To Both Water And Downtown!

4 4
house , Annapolis
This four-bedroom house is located in Annapolis, just 2 kilometres from Carrs Beach and 5 kilometres from Annapolis Harbour, offering a convenient base for exploring the city and the coastline. It has received excellent ratings for location, cleanliness, and overall experience.
The house features a private terrace and outdoor dining area, perfect for enjoying meals al fresco. Guests can also benefit from a fully equipped kitchen with a dishwasher, air conditioning, free private parking, Wi-Fi, a children's playground, a garden, and a washing machine.

Best Maryland villas and holiday homes with jacuzzi

Adorable Beach Cottage W/ Hot Tub & Tropical Bar! - Maryland
9.1 29 reviews
Maryland
03/09 – 07/09
SG$416/nighttotal: SG$1664 (4 )

Adorable Beach Cottage W/ Hot Tub & Tropical Bar!

2 4
house , Chesapeake Beach
This charming beach house is located in Chesapeake Beach, Maryland, just 48 kilometres from Addison Road-Seat Pleasant and 63 kilometres from Ronald Reagan Washington National Airport, offering easy access to both the city and the surrounding natural beauty. The property has received consistently high ratings for its cleanliness, location, and overall experience, making it a popular choice for travellers seeking a comfortable and enjoyable stay.
The property features two bedrooms and one bathroom, spanning 89 square metres and comfortably accommodating up to six guests. Enjoy a range of amenities including a fully equipped kitchen, a private hot tub, a balcony with stunning sea views, and a garden, perfect for relaxing and enjoying the beautiful Chesapeake Bay surroundings.
The Carraige House Of Mount Vernon - Maryland
10 2 reviews
Maryland
30/07 – 31/07
SG$546/nightfor 1 night

The Carraige House Of Mount Vernon

3 2
house , Baltimore
The Carriage House in Baltimore offers convenient access to Penn Station, a short walk from the Walters Art Museum, and within 2.4km of the Inner Harbour and Baltimore Convention Centre.
This three-bedroom, three-bathroom villa boasts 125 square metres of space, sleeping up to 11 guests and featuring a fully equipped kitchen, Wi-Fi, air conditioning, a jacuzzi, and a private balcony.
Spacious 6bed Woodland Retreat With Movie Room & Deck - Maryland
Maryland
10/09 – 13/09
SG$1456/nighttotal: SG$4368 (3 )

Spacious 6bed Woodland Retreat With Movie Room & Deck

7 7
house , California
This six-bedroom holiday home in California is situated 46.7 kilometres from New Carrollton and 8.7 kilometres from the Calvert Marine Museum, offering woodland tranquility and convenient parking with free Wi-Fi.
This expansive property boasts a fully equipped kitchen with a dishwasher and oven, a dedicated movie room, a fireplace, and a large deck with outdoor seating, accommodating up to 20 guests with a floor area of 557 square metres and a 11:00 AM check-out time.
Bamboo Sands Villa And Captains Lookout - Maryland
Maryland
10/09 – 13/09
SG$1703/nighttotal: SG$5109 (3 )

Bamboo Sands Villa And Captains Lookout

1 7
house , Betterton
This villa in Worton provides beachfront access and is located 77 kilometres from New Castle Airport.
The spacious 385 square metre property accommodates up to 23 guests with 4 bedrooms and 4 bathrooms, featuring a fully equipped kitchen, air conditioning, a jacuzzi, a garden, and an on-site tennis court, with water sports, fishing, canoeing, and hiking opportunities nearby.
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