St. Leonard holiday homes

We found 118 holiday rentals — enter your dates for availability

Discover a selection of 17 homes and other holiday rentals in St. Leonard that are perfect for your trip. Whether you're travelling with a group or just with your pet, holiday homes have the best amenities for spending time at your holiday home, including parking and a TV. You'll be sure to find a property to rent that has what everyone needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts - St. Leonard

Showing deals for:25 Jul - 1 Aug

Image gallery for Stunning Water Front Home with Private Dock and Beach and Sunsets

Sit on the patio and enjoy your coffee in the morning.
9.8 out of 10 rating
Exceptional
(19 reviews)

Stunning Water Front Home with Private Dock and Beach and Sunsets

Lusby, MD

8% off
Price is NZ$8,579
NZ$1,226 per night
includes taxes & fees
Stunning Water Front Home with Private Dock and Beach and Sunsets

Find spaces that suit your style

  • Peace of mind
    Our Book with Confidence guarantee gives you 24/7 support
  • More quality time
    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home
    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less
    More space, more privacy, more amenities — more value

Find the perfect holiday rental for your St. Leonard getaway

The area's wineries and museums are just some of the reasons to come on holiday to St. Leonard. This city's shopping, sporting events and restaurants draw many visitors. Are you looking for specific amenities for your getaway? Many of our holiday rentals feature full kitchens and laundry facilities.

Activities and attractions in St. Leonard

Are you looking for top things to see and do during your stay? Venture out of your cosy holiday rental and check out everything that makes St. Leonard a fun place to get away to. These are some of the top attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Perigeaux Vineyards and Winery (3.8 mi / 6.1 km)
  • Running Hare Vineyard (6.7 mi / 10.8 km)
  • Port of Leonardtown Winery (14.3 mi / 23.1 km)
  • Chesapeake Beach Water Park (15.1 mi / 24.3 km)
  • Maryland International Raceway (18.3 mi / 29.5 km)
  • Breton Bay Golf Course (16.7 mi / 26.8 km)

Exploring the natural landscape of St. Leonard

Whether you're looking for fun outdoor activities or just want to appreciate the scenery, St. Leonard is a great place to get outside. These are some of the area's most enchanting features, all within 30 miles (48.2 km) of the city centre:

  • Matoaka Beach (1.5 mi / 2.4 km)
  • Battle Creek Cypress Swamp Sanctuary (4.7 mi / 7.5 km)
  • Cove Point Beach (9.1 mi / 14.7 km)
  • Annmarie Sculpture Garden and Arts Center (9.4 mi / 15.1 km)
  • Breezy Point Beach (10.1 mi / 16.3 km)
  • St. Mary's River State Park (14.9 mi / 24 km)

Transport to and around St. Leonard

The nearest airport is in Ronald Reagan National Airport (DCA), located 38.8 mi (62.4 km) from the city centre.

Frequently asked questions

What is the most popular type of holiday home accommodation in St. Leonard?
According to our data, houses are the most popular type of holiday property in St. Leonard. But as you know, everyone’s idea of the perfect trip will differ. Bookabach has holiday homes of all shapes, sizes and budgets, so you’re sure to discover the best fit for your needs.
How much does it cost to rent a holiday home in St. Leonard?
The average price for a holiday home in St. Leonard depends on a number of factors, including length of stay, property type and season. Whether you’re in search of a sprawling villa with space for extended family or a quaint cabin perfect for just you and the kids, just add your dates of travel to find stays with amazing value.
How much does it cost to rent a beach house in St. Leonard?
The average price for a holiday home close to the beach in St. Leonard depends on when you’re travelling and the size and type of property you’re searching for. Find prices quickly and easily on Bookabach by entering the dates you’ll be travelling. Then use our handy filter tool to pick the number of bedrooms and amenities that you prefer, like air conditioning, a pool and WiFi.
Are there pet-friendly holiday homes in St. Leonard?
Good news! Yes. You’ll have a choice of six holiday homes that allow pets in St. Leonard. Some of our pet-friendly holiday homes have an outdoor space for your four-legged fur baby to have fun in, complimentary treats, special dog beds and proximity to parks. Apply the “Pets allowed” filter to find your pawfect digs on Bookabach.
What are popular home amenities in St. Leonard?
Nearby museums, a nearby waterfront and a water view top the list of most popular home amenities in St. Leonard. Whether you plan to travel by yourself, with your significant other or a group of best friends, Bookabach will help you find a holiday home that fits your style with all the features you’ll enjoy.
Are there large group holiday homes in St. Leonard?
With three St. Leonard holiday properties that can accommodate five or more people, you can bring a few extra pals or family members along. Whether you’re planning an informal get-together or a celebratory event, we’ll help you find a comfy space to match the occasion.
Are there holiday homes in St. Leonard that welcome kids?
With six family-friendly holiday homes available in St. Leonard, now is an awesome time to introduce your children to the joys of travel. Simply click on our “Properties good for families” filter box to search for stays loaded with amenities ideal for holidaying families, like multiple bedrooms, backyards, bunk beds and entertainment areas.
What are the top attractions for families in St. Leonard?
Keeping the kids amused during your holiday in St. Leonard is easy with these fabulous family-friendly attractions:

  • R&Js PlayPark
  • Jefferson Patterson Park and Museum
  • Battle Creek Cypress Swamp Sanctuary

Can I find two-bedroom holiday homes in St. Leonard?
Take off with your besties and relax in total privacy and comfort in one of the three two-bedroom holiday homes St. Leonard has to offer.
Are there holiday homes with WiFi in St. Leonard?
St. Leonard has two holiday homes with WiFi, so you can stay connected while you’re away. Simply check the “WiFi” box in our search filter for a list of properties with this feature. From streaming Hollywood blockbusters to updating your social media, these Bookabach homes make it easy to go online.
How can I find holiday homes with air conditioning in St. Leonard?
You can choose from six Bookabach holiday homes with air conditioning in St. Leonard giving you that cool, cool breeze and extra level of comfort. Enter your chosen travel dates and then make use of our filter tool to find stays with air conditioning.
How old do you have to be to rent a holiday home in St. Leonard?
The age limit can differ across properties on Bookabach, so look at the rules of the holiday home in St. Leonard you’re interested in. But usually, it’s 16, 18 or 21.
How long can I rent a holiday home in St. Leonard for?
The amount of time you can stay in a St. Leonard holiday home for differs depending on the property. Simply tap in your travel dates to view options offering extended stays. They have all you require to make your extended trip more enjoyable and convenient, like kitchens and backyards. Some properties might also offer weekly or monthly discounts, so you can stay longer for less money.

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