Holiday Rentals in Maryland

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Maryland holiday rentals
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Best Holiday rentals and Airbnb offers in Maryland

Best family friendly Maryland holiday rentals

Among the 57371 accommodations in Maryland, here are the 4 best family friendly rentals

83 M² Apartment ∙ 2 Bedrooms ∙ 6 Guests - Maryland
Maryland
29/06 – 07/08
SG$351/nighttotal: SG$13689 (39 )

83 M² Apartment ∙ 2 Bedrooms ∙ 6 Guests

2 3
apartment , Catonsville
Apartment rental for up to 6 people. This accommodation is based in Catonsville.
Services and facilities include air conditioning, a kitchen and an iron. This apartment is very convenient for families.
Close To Us Naval Academy, Downtown Annapolis, Maryland Live Casino, Bwi Airport - Maryland
9.8 26 reviews
Maryland
27/06 – 13/07
SG$565/nighttotal: SG$9040 (16 )

Close To Us Naval Academy, Downtown Annapolis, Maryland Live Casino, Bwi Airport

4 5
apartment , Severna Park
This four-bedroom apartment is situated in Severna Park, a suburb of Annapolis, just a short drive from the US Naval Academy, Arundel Mills Mall, and Baltimore City. It has received excellent reviews from previous guests.
The property offers space for up to seven guests and includes two family rooms, a game room, and a built-in bar. Guests can enjoy a screened-in porch, a garden, and parking as well as access to internet, air conditioning, and a fully equipped kitchen.
Potomac Mansion Close To Nature, Culture & Dc - Maryland
8.6 4 reviews
Maryland
27/06 – 04/07
SG$2249/nighttotal: SG$15743 (7 )

Potomac Mansion Close To Nature, Culture & Dc

5 2
house , Potomac
This five-bedroom Potomac villa, situated within 9.6km of the Chesapeake & Ohio Canal, TPC Potomac at Avenel Farms, and Congressional Country Club, offers convenient access to local attractions and golfing.
The 836-square-metre property boasts a fully equipped kitchen, six bathrooms, and accommodates up to twelve guests, featuring a terrace, garden, and parking, alongside free Wi-Fi and laundry facilities.
Montpelier Spot Laurel Private Entrance & Parking - Maryland
Maryland
25/06 – 08/08
SG$197/nighttotal: SG$8668 (44 )

Montpelier Spot Laurel Private Entrance & Parking

1 2
apartment , South Laurel
This South Laurel apartment is situated within 1.6km of Montpelier Mansion and the Patuxent River, and within 4.8km of Capitol Technology University and Laurel Dinosaur Park.
The one-bedroom flat, sleeping two guests, offers two bathrooms, in-unit laundry, a fully equipped kitchen with fridge, microwave, dishwasher and oven, plus on-site parking and free internet access.

Top cities

Best pet friendly Maryland holiday rentals

Among the 57371 accommodations in Maryland, here are the 4 best pet friendly rentals

Elegant & Cozy Home Nestled In Maryland - Maryland
9.8 32 reviews
Maryland
16/08 – 23/08
SG$371/nighttotal: SG$2597 (7 )

Elegant & Cozy Home Nestled In Maryland

1 2
apartment , Severn
This four-bedroom, three-bathroom flat in Severn, Maryland, is conveniently located just 4 minutes from Fort Meade, 12 minutes from BWI Airport, and 6 minutes from Arundel Mills, placing you within a 48-kilometre radius of Washington D.C.
This single-level residence, accommodating up to 14 guests, boasts two primary suites, a modern kitchen with a dishwasher, air conditioning, fast Wi-Fi, a fenced garden, and entertainment options including foosball and a pool/ping-pong table, with a fitness centre and parking also provided.
Cozy 2 Bedroom, 2.5 Bath Across From Cambridge City Marina - Maryland
9.6 21 reviews
Maryland
03/07 – 04/07
SG$981/nightfor 1 night

Cozy 2 Bedroom, 2.5 Bath Across From Cambridge City Marina

2 2
apartment , Cambridge
This Cambridge city-centre townhouse, directly opposite the City Marina, offers easy access to the Harriet Tubman Underground Railroad National Historical Park and is within walking distance of the downtown area.
The two-bedroom, three-bathroom property sleeps five, boasts a terrace, garden, spa, parking, and is fully equipped with a fridge, microwave, dishwasher, and air conditioning; nearby activities include boating, birdwatching, and exploring the Richardson Maritime Museum and Ruark Boatworks.
Cozy Historic Guest House - Maryland
9.8 103 reviews
Maryland
10/07 – 11/07
SG$228/nightfor 1 night

Cozy Historic Guest House

1 2
house , Ellicott City
This Old Ellicott City studio apartment is situated a short walk from Main Street's shops and restaurants, offering easy access to the historic district.
The self-catering studio features a kitchenette with fridge, freezer and microwave, a full bathroom, sleeps two guests, and includes on-site parking (accessed via steps) and shared garden access; a portable heater/cooler is available.
Renovated Bungalow | Walk To Beach | Dog-friendly - Maryland
9.4 6 reviews
Maryland
01/07 – 31/07
SG$357/nighttotal: SG$10710 (30 )

Renovated Bungalow | Walk To Beach | Dog-friendly

2 5
apartment , Mayo
This Edgewater holiday home in Mayo is situated 2.1km from London Town and 2.4km from South River Golf Links, with Annapolis Harbour Center and the Smithsonian Environmental Research Center within 9.7km.
This 94 square metre property sleeps six guests in two bedrooms and one bathroom, and boasts a fully equipped kitchen, Wi-Fi, air conditioning, a private garden with barbecue, and parking; ideal for families.

Frequently asked questions about holiday rentals in Maryland

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

    For iconic Maryland sights, the Inner Harbour in Baltimore is a must, with its National Aquarium and historic ships. Then there's the United States Naval Academy in Annapolis, a stunning campus with a rich history. Fort McHenry in Baltimore, where the Star-Spangled Banner was inspired, is another key historical site. For a different perspective, explore the charming streets and architecture of historic Annapolis itself.
  • What are the best Airbnb and vacation rentals in Maryland?

  • Are there unique natural phenomena in Maryland, United States?

    Yes! Assateague Island National Seashore is famous for its wild horses. The Chesapeake Bay, the largest estuary in the United States, offers unique ecosystems and abundant wildlife viewing opportunities. You can also find stunning scenery in the Appalachian Mountains, which extend into western Maryland, offering hiking and breathtaking views.
  • What are the most popular Airbnbs in Maryland?

  • What essentials should you bring along for a trip to Maryland, United States?

    Comfortable walking shoes are a must, as are layers of clothing, as the weather can be unpredictable. Sunscreen and insect repellent are also recommended, especially during the warmer months. Don't forget a reusable water bottle, as staying hydrated is key, particularly when exploring outdoors.
  • What are the best vacation rentals with a pool in Maryland?

  • What famous events or festivals are happening in Maryland, United States?

    Maryland hosts many events. The Preakness Stakes, a prestigious horse race held annually in Baltimore, is a major event. Artscape, a large outdoor arts festival in Baltimore, is another popular choice. Numerous smaller, local festivals take place throughout the state, celebrating everything from seafood to local produce, depending on the time of year.
  • What are the best rentals for families and kids in Maryland?

  • Where can you find the best restaurants serving local dishes in Maryland, United States, and what are the must-try specialties?

    Baltimore's Inner Harbour area boasts many excellent seafood restaurants. Crab cakes are a Maryland staple, and you'll find countless variations. For a truly local experience, try Smith Island Cake, a unique layered dessert. Exploring different neighbourhoods will reveal many hidden gems offering delicious, authentic Maryland cuisine.
  • What are the best rentals or Airbnbs with a jacuzzi in Maryland?

  • What are some less-famous attractions in Maryland, United States that are worth a visit?

    Consider visiting the Catoctin Mountain Park, offering hiking and scenic views, or the Eastern Neck National Wildlife Refuge for birdwatching. The Chesapeake & Ohio Canal National Historical Park provides a peaceful escape and opportunities for cycling or walking along the historic towpath. These locations offer a quieter, more secluded experience than the more popular tourist spots.
  • What are the best activities for engaging with locals and understanding their culture in Maryland, United States?

    Visiting local farmers' markets is a great way to interact with Marylanders and sample regional produce. Attending smaller, local festivals can provide insights into community life and traditions. Simply striking up conversations with people in local bars or cafes can also offer a glimpse into the culture of the area.
  • What unique natural landscapes and terrain features can travellers explore in Maryland, United States?

    Maryland boasts diverse landscapes. The Chesapeake Bay offers stunning coastal scenery and waterways. The Appalachian Mountains in western Maryland provide opportunities for hiking and exploring mountainous terrain. The coastal plain in the east offers a different type of scenery, with beaches and wetlands.
  • How many days are ideal for a trip to Maryland, United States, and what are some itinerary suggestions?

    A long weekend (3-4 days) allows for a taste of Maryland's highlights, focusing on Baltimore and Annapolis. A week allows for a more in-depth exploration, potentially including a visit to the Eastern Shore or the Appalachian Mountains. A longer trip (10+ days) would allow for a more relaxed pace and the exploration of more niche interests.

Nearby regions

Best Maryland holiday rentals with a pool

Among the 57371 accommodations in Maryland, here are the 4 best rentals with a pool

Quiet Home 11 Mi To Andrews Afb: Family Friendly! - Maryland
Maryland
10/07 – 18/07
SG$771/nighttotal: SG$6168 (8 )

Quiet Home 11 Mi To Andrews Afb: Family Friendly!

3 3
house , Waldorf
This detached house in Waldorf is located 17.7 kilometres from National Harbor, 30.6 kilometres from Addison Road-Seat Pleasant, and 32.2 kilometres from Nationals Park, with Andrews Air Force Base a mere 17.7 kilometres away.
This air-conditioned property offers 186 square metres of living space with 3 bedrooms and 2 bathrooms, accommodating up to 15 guests with a fully equipped kitchen, complimentary WiFi, and a private swimming pool.
Rooftop Terrace & Grill | Walk To Metro | Woodmont Triangle - Maryland
9.0 4 reviews
Maryland
19/07 – 30/07
SG$335/nighttotal: SG$3685 (11 )

Rooftop Terrace & Grill | Walk To Metro | Woodmont Triangle

1 2
apartment , Bethesda
This one-bedroom flat is conveniently located in Bethesda's Woodmont Triangle district, just a short distance from the Walter Reed National Military Medical Center, NIH Clinical Center, and National Institute of Health Campus. It has received very good user ratings.
The flat is 68 square metres in size and can comfortably accommodate up to three guests. You can enjoy a range of amenities including a fully equipped kitchen, a balcony, a fitness centre, and a swimming pool.
Coconut Malorie 209 Condo - Maryland
8.0 1 review
Maryland
25/06 – 08/08
SG$691/nighttotal: SG$30404 (44 )

Coconut Malorie 209 Condo

1 3
apartment , Ocean City
Coconut Malorie 209 condo is located in Ocean City, a 5-minute walk from the beach and 2.2 kilometres from the Roland E. Powell Convention Centre.
This apartment offers accommodation for up to 7 guests with 1 bedroom and 1 bathroom, featuring a kitchen with microwave and toaster, free Wi-Fi, an outdoor swimming pool, and a hot tub.
Rosses Chance Guest House - Maryland
10 135 reviews
Maryland
20/07 – 23/07
SG$367/nighttotal: SG$1101 (3 )

Rosses Chance Guest House

1 2
house , Madison
This waterfront cottage, situated on a 16-acre estate on Hudson Creek in Maryland, offers a tranquil escape near Madison, though the precise distance to Madison requires clarification as the property is in Maryland.
The self-catering property comprises one bedroom, one bathroom, sleeping up to two guests, and features a fully equipped kitchen, swimming pool, and access to kayaking and fishing on Hudson Creek, alongside WiFi and air conditioning.

Best Maryland holiday rentals with parking

Walk To Everything House - Maryland
9.9 158 reviews
Maryland
10/07 – 13/07
SG$690/nighttotal: SG$2070 (3 )

Walk To Everything House

3 5
apartment , Easton
This charming house is located in St. Michaels, a short 1-kilometre walk from the Chesapeake Bay Maritime Museum, St. Michaels Museum, and St. Michaels Winery. The property has received excellent ratings for its location, cleanliness, and overall experience.
The house has three bedrooms and can accommodate up to six guests. It includes a fully equipped kitchen, a garden, a spa, and parking, providing everything you need for a comfortable and enjoyable stay.
Antietam House Historic Sharpsburg Retreat - Maryland
Maryland
27/06 – 04/07
SG$213/nighttotal: SG$1491 (7 )

Antietam House Historic Sharpsburg Retreat

1 2
house , Sharpsburg
The Antietam House Historic Sharpsburg Retreat offers a peaceful escape in Sharpsburg, situated approximately 24 kilometres from Harpers Ferry National Historical Park and 26 kilometres from the Appalachian Trail Conference Headquarters.
This air-conditioned holiday home, spanning 195 square metres, accommodates up to 11 guests with one bedroom, a fully equipped kitchen, and a private terrace, complemented by complimentary Wi-Fi and on-site parking.
Confortable Villa - Maryland
Maryland
07/07 – 07/08
SG$380/nighttotal: SG$11780 (31 )

Confortable Villa

5 4
house , New Carrollton
This five-bedroom villa is situated in Hyattsville, a short distance from New Carrollton, offering easy access to attractions such as Six Flags America and Washington Navy Yard.
The property, sleeping up to 12 guests, boasts two bathrooms with bidets, high-speed internet, air conditioning, and a variety of bed sizes across its five bedrooms.
1 Mi To The Metro! Centrally Located Apt Near Dc - Maryland
Maryland
07/07 – 07/08
SG$156/nighttotal: SG$4836 (31 )

1 Mi To The Metro! Centrally Located Apt Near Dc

1 4
apartment , Silver Spring
This Silver Spring flat offers convenient access to Washington D.C., situated 1 kilometre from the Red Line Metro and close to key employment hubs such as the National Oceanic and Atmospheric Administration and Holy Cross Hospital.
This 84 square metre flat, suitable for up to four guests, features a dedicated workspace with a monitor, a kitchenette equipped with a microwave oven, and off-street parking, with the Sligo Creek Trail located 800 metres away for outdoor pursuits.
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