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Villas and Holiday homes in Maryland

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20050 Villa rentals in Maryland

Lux Haven-cinema, Billiards, Office | Nest Nights. - Maryland
9.9 70 reviews
Maryland
2 3
SG$329/nighttotal: SG$2303 (7 )

Lux Haven-cinema, Billiards, Office | Nest Nights.

house - Germantown
This luxurious house is situated in Germantown, Maryland, just a short drive from Seneca Creek State Park and the Winter Lights Festival, offering a tranquil escape from the hustle and bustle of city life. It has received excellent ratings for location, cleanliness, and user experience.
The property features three bedrooms and two and a half bathrooms, comfortably accommodating up to six guests. It boasts a fully equipped kitchen, a home theatre, a game room with a pool table, a dedicated workspace, an outdoor deck, and access to a nearby lake.
Charming Vintage Cabin In The ️ Of Middletown. - Maryland
9.8 582 reviews
Maryland
2 1
SG$354/nightfor 1 night

Charming Vintage Cabin In The ️ Of Middletown.

cabin - Middletown
This charming cabin is situated in Middletown, just a short drive from local attractions such as wineries, cideries, and golf courses, offering a peaceful escape from the city while being close to activities. The cabin has received excellent ratings for its location, cleanliness, and overall user experience.
The cabin, with its 65 square metres of floor space, offers one bedroom and one bathroom. Guests can enjoy a fully equipped kitchen, a cosy fireplace, a terrace or balcony, a garden, parking, and amenities for relaxation and entertainment.
Historic Row Home In Downtown Annapolis - Maryland
10 3 reviews
Maryland
2 2
SG$1408/nightfor 1 night

Historic Row Home In Downtown Annapolis

house - Annapolis
This Annapolis property, a historic row house in Downtown Annapolis, is situated 1.8 km from Annapolis Harbour and 48 km from Baltimore's Inner Harbour and Camden Yards.
The 102-square-metre house offers two bedrooms, two bathrooms, sleeps ten guests, and includes a fully equipped kitchen, garden, Wi-Fi, and a washing machine.
Sweet Bamboo - Maryland
9.8 138 reviews
Maryland
2 3
SG$335/nighttotal: SG$670 (2 )

Sweet Bamboo

house - North Beach
This North Beach apartment is a short walk from the beach, boardwalk, and restaurants, and just five minutes from Chesapeake Beach. It has received excellent ratings for location, cleanliness, and user experience.
The three-bedroom property is spacious, with 89 square metres of floor area, and can comfortably accommodate up to six guests. The apartment is fully renovated and offers a range of amenities, including a well-equipped kitchen, air conditioning, a garden, a spa, parking, and internet access.
Sunrise Landing: Waterfront Cottage In Avenue! - Maryland
10 1 review
Maryland
2 1
SG$346/nighttotal: SG$692 (2 )

Sunrise Landing: Waterfront Cottage In Avenue!

house - Cobb Island
This waterfront cottage is situated in Avenue, Maryland, approximately 30 kilometres from Cape Saint Mary's Marina and within 40-48 kilometres of several attractions including the Calvert Marine Museum, Annmarie Sculpture Garden, Aqua-Land Marina, and St. Mary's College of Maryland.
This 67 square metre, one-bedroom property sleeps seven, offering direct dock access, a fully equipped kitchen, free Wi-Fi, cable TV, and a washing machine; guests can also enjoy outdoor dining and proximity to various water activities.
Chill In The Crib! Easton, Maryland - Maryland
10 652 reviews
Maryland
2 1
SG$274/nighttotal: SG$822 (3 )

Chill In The Crib! Easton, Maryland

B&B - Easton
This converted corn crib is located on Maryland's Eastern Shore, a short drive from the charming town of Easton and close to the Chesapeake Bay. It has received excellent ratings for its location, cleanliness, and overall experience.
The quaint cottage has one bedroom and one bathroom, suitable for a couple. It offers a private entrance, a peaceful garden, a spacious interior with a vaulted ceiling and skylights, and modern conveniences like air conditioning, Wi-Fi, and a comfortable Casper mattress.
Lower Level 1br Guest Suite Wparking Near Bwi - Maryland
Maryland
2 1
SG$240/nighttotal: SG$480 (2 )

Lower Level 1br Guest Suite Wparking Near Bwi

house - Elkridge
This Elkridge flat is located in Hanover, 7.2 kilometres from Carroll Park and within a 9.2-kilometre radius of Baltimore attractions such as the Inner Harbour and the University of Maryland – Baltimore.
This 208-square-metre residence accommodates up to eight guests with a fully equipped kitchen, air conditioning, and complimentary WiFi, plus a garden and private entrance, and is situated just 8 kilometres from Baltimore/Washington International Airport.
The Birdhouse On Swan Creek, Welcome! - Maryland
9.7 42 reviews
Maryland
2 1
SG$437/nighttotal: SG$874 (2 )

The Birdhouse On Swan Creek, Welcome!

house - Rock Hall
This one-bedroom apartment is conveniently located in Rock Hall, within a short walk of Ferry Park and Waterman’s Museum, and within a 2-mile radius of Rock Hall Harbor and The Mainstay. Guests have consistently rated this property excellent for location, cleanliness, and overall experience.
The apartment offers 74 square metres of space, comfortably accommodating up to three guests. The well-equipped kitchen, private balcony, and convenient amenities such as free Wi-Fi, parking, and barbecue grills ensure a comfortable and enjoyable stay.
Lakefront Log Home W/ Dock Slip, 30% Weekly Discount, 2 Miles From Nat. Park - Maryland
9.0 51 reviews
Maryland
2 6
SG$408/nighttotal: SG$2856 (7 )

Lakefront Log Home W/ Dock Slip, 30% Weekly Discount, 2 Miles From Nat. Park

cabin - Swanton
This charming cabin is situated just 0.2 kilometres from Deep Creek Lake and 2.7 kilometres from Deep Creek Lake State Park, offering a peaceful retreat in a picturesque setting. It has consistently received excellent guest reviews, making it a popular choice for travellers.
The spacious cabin spans 204 square metres and comfortably accommodates up to 12 guests across its six bedrooms. The property boasts a range of amenities, including a private swimming pool, a garden, a terrace, and a fully equipped kitchen, ensuring a relaxing and enjoyable stay.
Tree House Resort Spa With Sauna - Maryland
10 87 reviews
Maryland
2 1
SG$964/nightfor 1 night

Tree House Resort Spa With Sauna

cabin - Rosedale
This secluded cabin is located in a wooded area just 10 kilometres from Baltimore City, near Rosedale, offering a peaceful retreat for couples seeking a private getaway.
The self-contained cabin features a fully equipped kitchen, a private garden, and a shared heated swimming pool, perfect for relaxing after exploring the nearby attractions of Baltimore.
Chic Townhome W/ Deck: 6 Mi To Dtwn Baltimore - Maryland
8.9 72 reviews
Maryland
1 4
SG$293/nighttotal: SG$27249 (93 )

Chic Townhome W/ Deck: 6 Mi To Dtwn Baltimore

house - Baltimore
This townhome is located in Baltimore, just 7 kilometres from the city centre and within 8 kilometres of attractions such as Carroll Park, the Edgar Allen Poe Museum, and the Baltimore Convention Center, offering a peaceful retreat from the city bustle. The property has received excellent ratings for user experience, location, and cleanliness.
This 4-bedroom property spans 117 square metres and comfortably accommodates up to 7 guests. The townhome offers a range of amenities, including free Wi-Fi, a fully equipped kitchen, a private deck, a fitness room, and parking, making it an ideal choice for families or groups of friends.
Boatyard Bungalow, 6 Beds; 2 Full Baths-waterfront - Maryland
9.9 169 reviews
Maryland
9 4
SG$626/nighttotal: SG$2504 (4 )

Boatyard Bungalow, 6 Beds; 2 Full Baths-waterfront

bungalow - Edgemere
This Edgemere house, a former schoolhouse dating back to 1898, is situated near Tradepoint Atlantic, offering waterfront access and marina amenities.
The 204-square-metre property boasts four bedrooms, two bathrooms, sleeping up to ten guests, and includes a kitchen with dishwasher, air conditioning, a garden, parking, and access to kayaks and canoes.

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

Dreamcatcher Cabin ~Scenic Views With Big Sky Hues - Maryland
9.9 38 reviews
Maryland
2 3
SG$845/nightfor 1 night

Dreamcatcher Cabin ~Scenic Views With Big Sky Hues

cabin - Pondsville
This luxury log lodge is situated in the Catoctin Mountains, offering expansive views without precise proximity to Pondsville landmarks.
The 209 square metre property accommodates six guests with three bedrooms and three bathrooms, featuring a gourmet kitchen, two master suites, a lower-level lounge with a mini pool table, and extensive outdoor entertainment areas including a hot tub and gas grill, all supported by 1200 MBPS WiFi.
Family And Pet-friendly, Waterfront With Pier - Maryland
10 276 reviews
Maryland
2 4
SG$426/nighttotal: SG$852 (2 )

Family And Pet-friendly, Waterfront With Pier

cottage - Madison
This waterfront property is situated just a short drive from Cambridge, Maryland, offering easy access to nearby towns like Easton, St. Michaels, Salisbury, and Ocean City. The cottage enjoys an excellent user rating, reflecting its high standards and appeal to travellers.
This four-bedroom, two-bathroom home spans 174 square metres and comfortably accommodates up to eight guests. The property offers a range of amenities, including a swimming pool, jacuzzi, tennis court, and a fully equipped kitchen, perfect for families and groups seeking a relaxing and enjoyable stay.
Cool Spring Cove - Maryland
Maryland
2 4
SG$905/nighttotal: SG$4525 (5 )

Cool Spring Cove

house - Arnold
This waterfront residence in Cool Spring Cove, Arnold, Maryland, offers direct access to the Magothy River with a private pier, located approximately 12 kilometres from Downtown Annapolis and the U.S. Naval Academy.
This family-friendly property accommodates up to 10 guests with 4 bedrooms and 3 bathrooms, featuring a private swimming pool, a screened waterfront gazebo, a deck, a fully equipped kitchen, air conditioning, and high-speed internet, plus it is conveniently situated near family parks and dining establishments.
Oceanside Condo W Pool Steps To Beach - Maryland
10 1 review
Maryland
2 1
SG$226/nighttotal: SG$1582 (7 )

Oceanside Condo W Pool Steps To Beach

house - Ocean City
This detached house in Ocean City offers direct access to the beach, being just a short walk away and 4 kilometres from Northside Park, with Ocean City Harbour 7.2 kilometres distant.
This one-bedroom property, suitable for up to seven guests, features a private swimming pool, sea views, complimentary WiFi, private parking, and a fully equipped kitchen, and is located 4.2 kilometres from the Roland E. Powell Convention Centre and 6.1 kilometres from Thunder Lagoon Waterpark.

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

Oak House - Maryland
9.7 3 reviews
Maryland
2 4
SG$681/nighttotal: SG$1362 (2 )

Oak House

house - Silver Spring
Oak House, situated in Silver Spring, Maryland, offers convenient access to Washington D.C. attractions, lying within 10-13 kilometres of landmarks such as the National Gallery of Art and the US Capitol Building.
This Silver Spring property, boasting 11 square metres of floor space, comfortably accommodates up to 15 guests with two bedrooms, three bathrooms, free parking, Wi-Fi, and a fully equipped kitchen including oven and microwave; plus an on-site water park.
Hill Top Cottage With Chickens! - Maryland
10 21 reviews
Maryland
2 2
SG$224/nighttotal: SG$5600 (25 )

Hill Top Cottage With Chickens!

cottage - Darlington
This Darlington cottage, ideal for families, offers self-catering accommodation with a fully equipped kitchen including a dishwasher and washing machine, and is conveniently located near Darlington's attractions, though precise distances aren't specified.
Sleeping up to four guests in two bedrooms and one bathroom, the property features air conditioning, Wi-Fi, and in-cottage games, ensuring a comfortable and convenient stay.
Private Peninsula Estate, Pool Houses, Crab Shack - Maryland
9.9 166 reviews
Maryland
9 6
SG$2379/nighttotal: SG$9516 (4 )

Private Peninsula Estate, Pool Houses, Crab Shack

house - Tilghman Island
This beautiful six-bedroom house is situated on a peninsula at the tip of Neavitt fishing village, just a short distance from Tilghman Island, St. Michaels, and Choptank River. The property has received excellent ratings for its location, cleanliness, and overall experience, making it a great choice for families and groups. This spacious house can accommodate up to 12 guests, with multiple bedrooms, including a master suite with a freestanding tub and walk-in closet. Enjoy a private pool, a crab shack, a games room, and a variety of activities like fishing, kayaking, and biking, all while enjoying breathtaking views of the Chesapeake Bay and Choptank River.
Private, Above-ground Studio - Maryland
9.9 199 reviews
Maryland
2 1
SG$140/nighttotal: SG$280 (2 )

Private, Above-ground Studio

house - Takoma Park
This house is located in Takoma Park, a quiet residential neighbourhood just 3.2 kilometres from the Metro station, which provides direct access to Union Station, downtown DC, and the National Mall. The property has received excellent ratings for user experience, location, and cleanliness.
The accommodation offers a spacious private bedroom with its own entrance, bathroom, living area, and a children's play area, suitable for up to 2 guests. Guests can enjoy the backyard with an eating space and a clothesline, as well as keyless entry for a smooth check-in process.

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

Golden Sands 712 - Maryland
10 1 review
Maryland
4 2
SG$237/nighttotal: SG$2607 (11 )

Golden Sands 712

house - Ocean City
Golden Sands 712, a beachfront Ocean City apartment, is located 2.1km from Northside Park and within 9.7km of Ocean City's boardwalk and Jolly Roger amusement park.
This 101 square metre flat boasts two bedrooms, two bathrooms, sleeps eleven guests, and includes a terrace, swimming pool, sauna, fitness centre, tennis court, parking, and a well-equipped kitchen.
Craftsman Style Ridgetop Tiny House With A Hot Tub - Maryland
9.9 238 reviews
Maryland
2 1
SG$374/nighttotal: SG$748 (2 )

Craftsman Style Ridgetop Tiny House With A Hot Tub

house - Pecktonville
This one-bedroom cabin is situated on a 275-acre farm near Pecktonville, offering panoramic views of the Appalachian Mountains in Pennsylvania, Maryland, and West Virginia. The cabin features a fully equipped kitchen, a queen-sized loft bed, and access to the surrounding farmland, ideal for a peaceful retreat for two.
Updated North Beach Cottage: Pet Friendly! - Maryland
9.6 76 reviews
Maryland
2 3
SG$525/nighttotal: SG$1050 (2 )

Updated North Beach Cottage: Pet Friendly!

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.
Lighthouse Haven | An Esvr Property - Maryland
10 22 reviews
Maryland
2 6
SG$1722/nighttotal: SG$12054 (7 )

Lighthouse Haven | An Esvr Property

house - Stevensville
This waterfront property is located just a short distance from the Chesapeake Bay, and is within easy reach of the charming downtown area of Stevensville. The apartment has excellent user, location, and cleanliness ratings, making it a popular choice for travellers.
This spacious 6-bedroom home can comfortably accommodate up to 14 guests, and features a well-equipped kitchen, a peaceful sunroom, and access to a swimming pool, tennis court and garden. Guests also have access to a private terrace or balcony and enjoy stunning water views and direct access to Long Creek, perfect for kayaking, paddleboarding, or simply enjoying the serene surroundings.

Best Maryland villas and holiday homes with jacuzzi

Ski Harbor 45 - Maryland
8.5 60 reviews
Maryland
4 2
SG$234/nighttotal: SG$2574 (11 )

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.
Ultra Luxe Oceanfront Escape - Incredible Views - Maryland
9.3 4 reviews
Maryland
4 2
SG$378/nighttotal: SG$4158 (11 )

Ultra Luxe Oceanfront Escape - Incredible Views

house - Ocean City
This beachfront property in Ocean City offers direct access to Ocean City Beach, just a 4-minute walk away, and is situated 2.4 kilometres from Northside Park.
This holiday home, spanning 98 square metres, accommodates up to 15 guests with 2 bedrooms and 2 bathrooms, featuring an indoor swimming pool, jacuzzi, garden, parking, and a fully equipped kitchen with a dishwasher and oven, all accessible via a lift.
Cozy Modern Chesapeake Bay Home - Maryland
9.7 434 reviews
Maryland
2 2
SG$185/nighttotal: SG$4625 (25 )

Cozy Modern Chesapeake Bay Home

bungalow - Deale
This charming bungalow in Deale is just a short drive from Annapolis and offers stunning views of the Chesapeake Bay. It has received excellent ratings for its cleanliness, location and user experience.
The property has two bedrooms and one bathroom, comfortably accommodating up to four guests. Enjoy the outdoor spa, kayaking on the bay, and explore the local seafood scene, all within easy reach of the bungalow.
New! Private Luxury Spa Hot Tub Retreat With Ping Pong - Maryland
10 1 review
Maryland
2 3
SG$1596/nighttotal: SG$7980 (5 )

New! Private Luxury Spa Hot Tub Retreat With Ping Pong

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.
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