Holiday Rentals in Maryland

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Maryland holiday rentals
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57371 Holiday Rentals and Airbnb in Maryland

Best family friendly Maryland holiday rentals

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

Chester River Waterfront, Magnificent Views, Dock, Beach, Close 2 Town - Maryland
9.7 124 reviews
Maryland
13/07 – 14/08
NZ$631/nighttotal: NZ$20192 (32 )

Chester River Waterfront, Magnificent Views, Dock, Beach, Close 2 Town

3 5
apartment , Kingstown
This waterfront property is situated just 14.5 kilometres from Washington College, River Arts Chestertown, and Rolphs Wharf Marina, offering easy access to local attractions and a peaceful setting. The home has received excellent ratings for cleanliness, location, and user experience, making it a popular choice for travellers.
The house spans 139 square metres and comfortably accommodates up to six guests. It offers a range of amenities, including a fully equipped kitchen, air conditioning, a terrace, a garden, a spa, a bar, parking, and free breakfast, ensuring a comfortable and enjoyable stay.
Extended Loft. Near At, C&o, Harper`s Ferry - Maryland
Maryland
15/10 – 18/10
NZ$396/nighttotal: NZ$1188 (3 )

Extended Loft. Near At, C&o, Harper`s Ferry

2 2
apartment , Brunswick
This combined apartment in downtown Brunswick is located on the waterfront, a short walk from the C&O Canal and Potomac River, and 10 kilometres from Harper's Ferry.
This family-friendly flat accommodates up to 10 guests with three bedrooms, a shared full kitchen and bathroom, air conditioning, internet, terrace, and parking, offering flexible privacy options and secure bike storage, with nearby access to restaurants, shops, the museum, train station, and outdoor pursuits including the Appalachian Trail.
Beautiful Renovated Cottage At Ironman Start Line - Maryland
9.9 28 reviews
Maryland
10/07 – 18/07
NZ$340/nighttotal: NZ$2720 (8 )

Beautiful Renovated Cottage At Ironman Start Line

2 3
apartment , Cambridge
This Cambridge holiday home is situated in the historic district, directly opposite GB Marsh Park and a short walk from the Eagleman/Ironman triathlon start line.
The recently renovated two-bedroom property sleeps five, boasts a spacious layout with multiple seating areas, a well-equipped kitchen including a dishwasher, and a large enclosed garden; ample parking is available for boats, bikes, and other sporting equipment.
Close To Us Naval Academy, Downtown Annapolis, Maryland Live Casino, Bwi Airport - Maryland
9.8 26 reviews
Maryland
01/07 – 02/08
NZ$709/nighttotal: NZ$22688 (32 )

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

4 2
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.

Top cities

Best pet friendly Maryland holiday rentals

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

Pet-friendly Beach Getaway, Relax By The Bay! - Maryland
10 6 reviews
Maryland
10/09 – 13/09
NZ$775/nighttotal: NZ$2325 (3 )

Pet-friendly Beach Getaway, Relax By The Bay!

3 7
apartment , Arnold
This Annapolis apartment, situated 14.8 km from Annapolis Harbour and 43.5 km from Baltimore's Inner Harbour and Camden Yards, offers convenient access to waterfront activities and city attractions.
This 188 square metre property features two bedrooms, three bathrooms, a fully equipped kitchen, free Wi-Fi, private parking, and a balcony; comfortably accommodating up to 15 guests.
Smallwood St Park, Groups, Fire Pit, Blackstone, Large Parking Area - Maryland
9.6 34 reviews
Maryland
01/08 – 04/08
NZ$749/nighttotal: NZ$2247 (3 )

Smallwood St Park, Groups, Fire Pit, Blackstone, Large Parking Area

2 14
apartment , Potomac Heights
This Marbury holiday home is situated in a rural area, within 3.2km of the Mattawoman Natural Environment Area and Mattawoman State Natural Environmental Area, and within 4.8km of Smallwood State Park.
This 139 square metre property boasts two bedrooms, three bathrooms, sleeps 30 guests, and includes a swimming pool, jacuzzi, and private garden with gas grills, alongside free Wi-Fi.
Historic Home In Union Square, Baltimore. - Maryland
Maryland
17/07 – 16/10
NZ$117/nighttotal: NZ$10647 (91 )

Historic Home In Union Square, Baltimore.

2 3
apartment , Baltimore
This fully renovated 2-bedroom flat is located in Baltimore's Union Square district, providing convenient access to the National Aquarium, approximately 2.5 kilometres away, and the Inner Harbour.
This property accommodates up to four guests and features a smart TV, wireless internet, an in-unit washer and dryer, and private parking for two vehicles, with enhanced security measures including an alarm system and surveillance cameras.
Kick Back And Enjoy The Chesapeake & This 3-bedroom, Relaxing, Stylish Space. - Maryland
9.0 8 reviews
Maryland
24/07 – 27/07
NZ$914/nighttotal: NZ$2742 (3 )

Kick Back And Enjoy The Chesapeake & This 3-bedroom, Relaxing, Stylish Space.

3 10
apartment , Prince Frederick
This three-bedroom, two-bathroom house in Prince Frederick offers Chesapeake Bay views and is conveniently located near R&J's PlayPark and Running Hare Vineyard, with Chesapeake Beach Railway Museum and Water Park also within driving distance.
Sleeping up to ten guests comfortably, this newly renovated, two-level property boasts a fully equipped kitchen, banquette dining area, two king beds, one queen bed, two sofa beds, and two rollaway beds, plus internet and air conditioning.

Frequently asked questions about holiday rentals in Maryland

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

    Maryland offers a fantastic mix of history and nature. For history buffs, a visit to the Inner Harbour in Baltimore, with its maritime museum and historic ships, is essential. Fort McHenry, where the Star-Spangled Banner was inspired, is another must-see. Annapolis, the state capital, boasts the United States Naval Academy and charming colonial architecture. For a different perspective, explore the historic district of St. Mary's City, the first English settlement in Maryland.
  • What are the best Airbnb and holiday rentals in Maryland?

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

    Assateague Island National Seashore is famous for its wild horses, a truly unique sight. The Chesapeake Bay, the largest estuary in the United States, offers stunning natural beauty and diverse wildlife. The Great Falls of the Potomac River provide a dramatic display of nature's power.
  • What are the most popular Airbnbs in Maryland?

  • What essentials should you bring to Maryland, United States?

    Depending on the time of year, pack comfortable walking shoes, as you'll likely be doing a lot of exploring. Layers are a good idea, as the weather can be unpredictable. Sunscreen and insect repellent are also recommended, especially during the warmer months. Don't forget your camera to capture all the amazing sights!
  • What are the best holiday rentals with a pool in Maryland?

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

    Maryland hosts many events throughout the year. The Preakness Stakes, a renowned horse race, takes place annually in Baltimore. Numerous smaller festivals celebrate local produce and culture, such as the Maryland Seafood Festival. Check local listings for specific dates.
  • 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 has many restaurants offering fresh seafood. Crab cakes are a Maryland staple, and you'll find countless variations. Smith Island Cake, a unique layered dessert, is another must-try. Many smaller towns and cities throughout the state have excellent restaurants showcasing local produce and 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 trails and stunning views. The Chesapeake & Ohio Canal National Historical Park provides a peaceful escape, perfect for cycling or walking along the canal towpath. The Edgar Allan Poe House and Museum in Baltimore offers a fascinating glimpse into the life of the famous author.
  • 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 people and sample regional produce. Attending smaller, local festivals or events will give you a feel for the community spirit. Striking up conversations with people in local bars and restaurants can also be a rewarding experience.
  • What unique natural landscapes and terrain features can travellers explore in Maryland, United States?

    Maryland's geography is diverse. The Chesapeake Bay offers stunning coastal scenery. The Appalachian Mountains in Western Maryland provide opportunities for hiking and exploring mountainous terrain. The Eastern Shore offers a flatter landscape with farmland and wetlands.
  • How many days are ideal for a visit 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, including the Eastern Shore and Western Maryland. Two weeks would enable a more leisurely pace, allowing for thorough exploration of the state's diverse landscapes and attractions.

Nearby regions

Best Maryland holiday rentals with a pool

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

Centreville Waterfront Farm | 170 Acres | Pool | Private Dock | Private Beach | - Maryland
10 14 reviews
Maryland
15/10 – 18/10
NZ$2007/nighttotal: NZ$6021 (3 )

Centreville Waterfront Farm | 170 Acres | Pool | Private Dock | Private Beach |

4 2
apartment , Queenstown
This waterfront property is conveniently located just 14.5 kilometres from Earle Landing, Hazel Miner Monument, and Queenstown Premium Outlets, offering easy access to local attractions and shopping. The house has consistently received excellent ratings for user experience, location, and cleanliness, ensuring a comfortable and enjoyable stay.
The spacious four-bedroom house spans 260 square metres and comfortably accommodates up to 10 guests. This family-friendly home features a private pool, a fireplace, a fully equipped kitchen, free Wi-Fi, BBQ grills, a garden, and a tennis court, providing ample opportunities for relaxation and entertainment.
43 Acre Private Retreat For The Whole Family Within Minutes Of Dc - Maryland
10 2 reviews
Maryland
28/06 – 29/06
NZ$3190/nightfor 1 night

43 Acre Private Retreat For The Whole Family Within Minutes Of Dc

5 2
apartment , Indian Head
The Amara Retreat Estate is a private luxury compound situated in Nanjemoy, Southern Maryland, offering seclusion 72 kilometres from Washington, DC, and 32 kilometres from Waldorf.
This expansive 697 square metre property comprises a 6-bedroom Main House, a Guest House, and a Glam Barn event space, accommodating up to 24 guests with amenities including a chef's kitchen, seasonal swimming pool, and firepits.
Rooftop Pool & Lounge In Downtown Charm Free Indoor Parking - Maryland
Maryland
22/09 – 25/09
NZ$328/nighttotal: NZ$984 (3 )

Rooftop Pool & Lounge In Downtown Charm Free Indoor Parking

1 3
apartment , Baltimore
This downtown Baltimore flat offers a prime location, situated within walking distance of the Inner Harbour, Baltimore Convention Centre, and Power Plant, with Baltimore-Washington International Airport approximately 14 kilometres away.
This residence provides a rooftop pool with city views, complimentary indoor and private parking, a fitness centre, spa facilities, and a 24-hour front desk, alongside full kitchen amenities and free WiFi.
3 Bedroom W Indoor Pool Hotub - Maryland
8.6 11 reviews
Maryland
01/08 – 30/08
NZ$476/nighttotal: NZ$13804 (29 )

3 Bedroom W Indoor Pool Hotub

3 2
house , Wheaton
This five-bedroom house is situated in Silver Spring, Maryland, just 14.5 kilometres from the Phillips Collection and a short drive from the Walter E Washington Convention Centre and the White House. The property boasts a private indoor pool and hot tub, a well-equipped kitchen with a dishwasher, a terrace with garden views, and ample parking, making it ideal for families or groups of up to 19 guests.

Best Maryland holiday rentals with parking

Charming Annapolis Waterview Home - Maryland
9.7 265 reviews
Maryland
01/08 – 04/08
NZ$1439/nighttotal: NZ$4317 (3 )

Charming Annapolis Waterview Home

4 14
apartment , Highland Beach
This charming Annapolis home is located on Chestnut Avenue, just 45 metres from the Chesapeake Bay, offering stunning water views and easy access to the beautiful Thomas Point and Quiet Waters parks. The property has consistently received excellent ratings for location, cleanliness, and overall user experience.
This spacious four-bedroom house, spanning 279 square metres, comfortably accommodates up to 14 guests. The property offers a range of amenities, including a fully equipped kitchen, a Jacuzzi, a terrace, a garden, a spa, and parking, as well as access to a community beach, fishing piers, and crabbing facilities.
3br Silver Spring Near Dc - Pet Friendly - Maryland
9.6 8 reviews
Maryland
13/07 – 14/08
NZ$325/nighttotal: NZ$10400 (32 )

3br Silver Spring Near Dc - Pet Friendly

3 5
apartment , Silver Spring
This Silver Spring flat is situated a 9-minute walk from the Baltimore & Ohio Railroad station and a 3-minute drive from Rock Creek Park.
This 86 square metre property offers three bedrooms and one bathroom, accommodating up to seven guests with amenities including air conditioning, Wi-Fi, a full kitchen, and in-unit laundry.
Charming Historic Victorian 4 Bedroom Guesthouse In  Rohrersville With Wifi, Ac - Maryland
9.8 10 reviews
Maryland
11/07 – 12/07
NZ$833/nightfor 1 night

Charming Historic Victorian 4 Bedroom Guesthouse In Rohrersville With Wifi, Ac

4 8
apartment , Rohrersville
This Rohrersville guesthouse is situated in the peaceful northern part of the town, near Rohrer's Mill Farm, and within a few kilometres of Big Cork Winery, the Appalachian Trail, Harper's Ferry, and the Antietam Battlefield.
The four-bedroom Victorian house, sleeping eight guests, boasts modern marble bathrooms, queen-size beds, Wi-Fi, air conditioning, and a private deck; nearby activities include kayaking, canoeing and hiking.
Z Presidential Suite - Maryland
9.3 8 reviews
Maryland
29/06 – 07/08
NZ$311/nighttotal: NZ$12129 (39 )

Z Presidential Suite

1 3
apartment , Queenland
The Z Presidential Suite is situated in Upper Marlboro, Maryland, 23 kilometres from the Supreme Court and the US Capitol.
This spacious one-bedroom apartment, spanning 186 square metres, comfortably accommodates up to 11 guests and features a fully equipped kitchen, a private terrace with garden views, and access to on-site amenities such as a bar, tennis courts, and a pool table.
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