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

Deep Creek Village #20 - Maryland
9.6 29 reviews
Maryland
15/10 – 18/10
SG$375/nighttotal: SG$1125 (3 )

Deep Creek Village #20

3 6
house , Accident
This three-bedroom apartment is located in Deep Creek Village 20, McHenry, Maryland, approximately 64 kilometres from Morgantown Municipal Airport and just a short drive from the popular Deep Creek Lake. The property has received excellent ratings for its location, cleanliness, and overall user experience.
The apartment offers plenty of space for families or groups of friends. Guests can enjoy modern amenities such as free Wi-Fi, a fully equipped kitchen, a washing machine, and access to a garden, tennis court, and restaurant.
Waterfront. Spacious. Hottub. Kayaks. Dogfriendly. - Maryland
10 97 reviews
Maryland
17/07 – 24/07
SG$431/nighttotal: SG$3017 (7 )

Waterfront. Spacious. Hottub. Kayaks. Dogfriendly.

1 5
apartment , Broomes Island
This luxurious waterfront property in Broomes Island, Southern Maryland, boasts direct access to Cat Creek and is approximately 80 kilometres from Washington, D.C., offering secluded estuary views.
The four-bedroom, four-bathroom holiday home features a spacious layout with two living areas, a game room with ping pong, a hot tub, private dock, kayaks, and fast Wi-Fi, accommodating up to six guests.
Prime Spot Staysimple Comfort, Perfect Location - Maryland
10 3 reviews
Maryland
17/07 – 24/07
SG$415/nighttotal: SG$2905 (7 )

Prime Spot Staysimple Comfort, Perfect Location

3 5
apartment , Annapolis
This 3-bedroom flat is located a mere 160 metres from historic Downtown Annapolis, providing straightforward walking access to the U.S. Naval Academy, City Dock, and the Maryland State House.
Offering 118 square metres of living space, this accommodation can host up to 8 guests and includes a fully equipped kitchen with a fridge, microwave, and dishwasher, plus air conditioning and parking.
* Private Suite Full Of Style & Comfort * - Maryland
9.0 47 reviews
Maryland
26/06 – 28/06
SG$202/nighttotal: SG$404 (2 )

* Private Suite Full Of Style & Comfort *

1 2
apartment , Lutherville
This one-bedroom apartment is situated in Lutherville Timonium, just 5km from Goucher College, Loch Raven Reservoir, and Towson Town Center, offering easy access to a range of attractions and amenities. It has received excellent user ratings, indicating a high level of satisfaction from previous guests.
The apartment comfortably accommodates up to four guests and features a fully equipped kitchen, a washing machine, a terrace, a garden, and parking. Enjoy a relaxing stay with access to a range of amenities, including a Smart TV, DVD player, and air conditioning.

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Best pet friendly Maryland holiday rentals

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

Tranquility Awaits - Maryland
10 26 reviews
Maryland
11/07 – 16/07
SG$309/nighttotal: SG$1545 (5 )

Tranquility Awaits

2 4
apartment , Crownsville
This apartment is conveniently located in Annapolis, just 3km from the Annapolis Bowl, Eisenhower Golf Course, and Annapolis Mall Shopping Centre. The surrounding area offers a mix of entertainment, shopping, and dining options, making it an ideal base for exploring Crownsville. This apartment has received excellent guest ratings, highlighting its comfortable and well-equipped nature.
This two-bedroom property, spanning 70 square meters, comfortably accommodates up to five guests. The apartment features a fully equipped kitchen, a terrace or balcony, a garden, a spa, and parking, ensuring a relaxing and enjoyable stay.
Bin There Treehouse, A Grain Bin Treehouse! - Maryland
Maryland
19/08 – 23/08
SG$229/nighttotal: SG$916 (4 )

Bin There Treehouse, A Grain Bin Treehouse!

1 3
house , Cavetown
The Bin There Treehouse, a unique grain bin lodging, is situated in Smithsburg, approximately 40 kilometres from historical sites such as Sachs Covered Bridge and Gettysburg Seminary Ridge Museum, with Hagerstown Regional Airport 21 kilometres away.
This 14 square metre dwelling, ideal for up to five guests, offers a cosy fireplace, a kitchenette, air conditioning, free WiFi, private parking, and one bedroom and bathroom.
Equestrian Escape! Quiet Farm Stay Near Gettysburg - Maryland
9.8 103 reviews
Maryland
22/09 – 25/09
SG$284/nighttotal: SG$852 (3 )

Equestrian Escape! Quiet Farm Stay Near Gettysburg

1 3
house , Union Bridge
This charming one-bedroom cottage is located in Keymar, Maryland, just a short drive from the historic sites of Gettysburg, including Little Round Top and Devil's Den. The property enjoys excellent user, location and cleanliness ratings.
The 111 square metre property comfortably accommodates four guests and features a fully equipped kitchen, a spacious living area, a relaxing patio, and a private spa. You can enjoy the peace and quiet of the surrounding countryside, or take advantage of the nearby amenities and attractions.
Waterfront Relaxing Getaway - Maryland
10 27 reviews
Maryland
10/09 – 13/09
SG$418/nighttotal: SG$1254 (3 )

Waterfront Relaxing Getaway

4 7
apartment , Cobb Island
This Cobb Island waterfront property offers stunning views and direct water access, situated 0.5km from St Clement's Island State Park and 2.7km from the Potomac River.
This four-bedroom, two-bathroom holiday home sleeps eight guests and boasts a fully equipped kitchen, barbecue facilities, ample parking (including for RVs), and amenities such as a Smart TV and washing machine.

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

Waterfront Paradise With Pool & Hot Tub Plus 4 King Beds & 4 Full Baths - Maryland
10 80 reviews
Maryland
27/06 – 04/07
SG$1380/nighttotal: SG$9660 (7 )

Waterfront Paradise With Pool & Hot Tub Plus 4 King Beds & 4 Full Baths

5 2
apartment , California
This California waterfront property is situated 0.6km from St. Mary's College of Maryland and 3.2km from Historic St. Mary's City, offering easy access to local attractions.
Sleeping nine guests, this five-bedroom, four-bathroom house boasts a private fenced yard, swimming pool, Jacuzzi, terrace, and free Wi-Fi; gas grills are available for outdoor dining, and the fully equipped kitchen includes a fridge, microwave, and dishwasher.
Rod 'N' Reel Resort - Maryland
8.6 1686 reviews
Maryland
27/06 – 04/07
SG$341/nighttotal: SG$2387 (7 )

Rod 'N' Reel Resort

1 2
resort , Chesapeake Beach
Rod 'N' Reel Resort is situated on the Chesapeake Bay, a short drive from North Beach and Twin Shields Golf Club, making it a convenient base for exploring the area. The resort enjoys excellent ratings for its location, cleanliness, and overall experience.
The resort offers a range of accommodation options, including rooms with balconies and water views. Guests can enjoy a variety of amenities, including a swimming pool, fitness centre, spa, and on-site dining options, as well as activities like fishing charters and casino entertainment.
House ∙ 4 Bedrooms ∙ 10 Guests - Maryland
10 1 review
Maryland
25/06 – 08/08
SG$454/nighttotal: SG$19976 (44 )

House ∙ 4 Bedrooms ∙ 10 Guests

4 3
house , Oakland
This luxurious four-bedroom, three-bathroom property is situated in Western Maryland, a specific distance from nearby landmarks not being provided.
Offering a swimming pool, jacuzzi, spa, and fitness centre, this spacious house sleeps ten guests and includes a fully equipped kitchen, internet access, and ample parking.
Live Exceptionally: Stylish 2-bedroom In An Elite, One-of-a-kind Community - Maryland
Maryland
04/09 – 07/09
SG$231/nighttotal: SG$693 (3 )

Live Exceptionally: Stylish 2-bedroom In An Elite, One-of-a-kind Community

2 2
apartment , Owings Mills
This two-bedroom flat in Owings Mills offers proximity to entertainment at Bowlero Pikesville and Diamond Ridge Golf Course, as well as natural escapes such as Mardella Ridge Forest Buffer Forest Conservation Reservation and Patapsco Valley State Park, all within a 5 kilometre radius.
This 116 square metre apartment accommodates up to 11 guests, featuring two bathrooms, high-speed WiFi, air conditioning, and access to resort-style amenities including a fitness centre and pool.

Best Maryland holiday rentals with parking

Studio 6 Gaithersburg Cozy King Nsmk Kitchen - Maryland
9.8 25 reviews
Maryland
15/10 – 18/10
SG$162/nighttotal: SG$486 (3 )

Studio 6 Gaithersburg Cozy King Nsmk Kitchen

1 2
apartment , Gaithersburg
This Gaithersburg flat is located 45 kilometres from Ronald Reagan Washington National Airport, with the US Marine Corps War Memorial 38 kilometres and the White House 39 kilometres away.
This 28 square metre studio apartment accommodates two guests and features a full kitchen, air conditioning, and on-site parking, with a fitness centre and picnic area available.
149 M² House ∙ 4 Bedrooms ∙ 10 Guests - Maryland
Maryland
17/07 – 16/10
SG$333/nighttotal: SG$30303 (91 )

149 M² House ∙ 4 Bedrooms ∙ 10 Guests

4 3
house , Greenbelt
Book this vacation rental for 10 people. This accommodation is located in Greenbelt.
Facilities and services: a terrace, air conditioning and a garden.
Waterfront Romantic Studio - Maryland
10 52 reviews
Maryland
28/06 – 29/06
SG$213/nightfor 1 night

Waterfront Romantic Studio

1 2
apartment , Dundalk
This Dundalk studio apartment, near Baltimore, offers convenient access to waterfront views and nearby state parks, located approximately 32 kilometres from the city.
The self-contained unit sleeps two, features a fully equipped kitchen with dishwasher, a private garden, parking, and boasts a shared deck with stunning water views, a fire pit, and proximity to scenic hiking trails.
Deep Creek Lake Townhome W/ Deck & Water Views - Maryland
9.6 54 reviews
Maryland
14/12 – 17/12
SG$328/nighttotal: SG$984 (3 )

Deep Creek Lake Townhome W/ Deck & Water Views

2 5
house , Oakland
This comfortable townhome in Oakland, Maryland is situated just a short distance from Deep Creek Lake, offering easy access to a range of water activities. It consistently receives excellent reviews for its location, cleanliness, and overall experience.
The property features two bedrooms, three bathrooms, and a spacious 139 square metres, comfortably accommodating up to six guests. Amenities include a fully equipped kitchen, air conditioning, free Wi-Fi, a deck with water views, and a garden, ensuring a relaxing and enjoyable stay.
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