St. Leonard Holiday Rentals from AU$390: Search Short-Term Rentals

Q: What are some of the best holiday rentals that St. Leonard has to offer?

Private 2 Acre Waterfront Family Retreat with Pool & Pier : This holiday home rental outside of St. Leonard is located on the waterfront, and has an outdoor pool, a balcony and a BBQ to put you at ease in your new surroundings. It has 8 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of books.

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Our top choices for St. Leonard holiday rentals

A bedroom with a bed, a fireplace, a ceiling fan, and a painting of a beach.

1. 3-bedroom house in soothing Saint Leonard with AC for relaxing stays

Saint Leonard

Nancy P.

includes taxes & fees

2 Nov - 3 Nov

A lakeside view with chairs and a table, a rainbow, and trees.

2. Bright and airy waterfront getaway

Benedict

George

includes taxes & fees

2 Nov - 3 Nov

A modern kitchen with a central island, stainless steel appliances, and a window with butterfly decals.

3. The Cozy Crab- Your Charming Haven in Lovely North Beach!

North Beach

James L.

includes taxes & fees

25 Oct - 26 Oct

An outdoor dining area with string lights, wooden tables, and chairs, overlooking a marina with boats.

4. Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

North Beach

Sarah

includes taxes & fees

25 Oct - 26 Oct

A beach with a rocky shoreline, a swimming area, and multi-story buildings in the background.

5. Beachside Oasis with Beach Passes & King Suite by A Haven Away

North Beach

Johanna S.

includes taxes & fees

9 Nov - 10 Nov

A grassy area with a stone path leading to a seating arrangement under trees, overlooking a body of water.

6. Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.

Benedict

ed r.

includes taxes & fees

24 Oct - 25 Oct

A kitchen with white cabinets, a stainless steel refrigerator, a microwave, a stove, and a sink.

7. Waterfront Getaway with Dock

Woolford

Meagan G.

includes taxes & fees

25 Oct - 26 Oct

A modern kitchen with granite countertops, stainless steel appliances, and large windows offering views of the outdoors.

8. 2 Acre Oasis with Private Beach! Family and dog friendly!

Leonardtown

Carol L.

includes taxes & fees

26 Oct - 27 Oct

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Top St. Leonard Hotel Reviews

Historic 1825 Chesapeake Farm Stay

10/10 Excellent

"Everything about this home is amazing! I loved chatting with the owner of the home and seeing the property! All the food was to die for!!! On top of all this it was so close to places for me to shark tooth hunt!!! 10 out of 10! Will be going back!!!"

Hilton Garden Inn Solomons

8/10 Good

"The room was clean and away from the elevators with no issues for the specific room. The only reason this is not a 5 star review is that there is no accommodation for customers / guests that need a nightstand on both sides of the bed. In our situation both customers have a CPAP machine. The reservation was for 2 guests and the room was a queen bed and upon arrival we had to decide who was going to sleep without their CPAP machine because the room has no bedside table or electrical outlets on the outer edge of the bed. Regardless of the medical need when will Hotels learn that both sides of the bed need a place to hold their CPAP or book or tea."

Welcome to Hickory House on the Chesapeake Bay!

10/10 Excellent

"This cozy home was perfect for two and would easily accommodate three. The kitchen had everything we needed, the bathroom was clean, the beds comfortable. It's an easy walk to the closest beach and a longer walk but very short drive to the nearest fossil hunting location (FlaggsPond). Theresa was very responsive to our questions while we were there. I'd definitely stay at Hickory House again."

Find out more about St. Leonard

Everything you need to know about St. Leonard holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the St. Leonard holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect St. Leonard holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search.

St. Leonard holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in St. Leonard. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A St. Leonard holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of St. Leonard holiday rentals we have selected for you start as low as AU$390 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on St. Leonard rentals

At Expedia, we put the best St. Leonard holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top St. Leonard rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream St. Leonard holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around St. Leonard. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Can I find a holiday rental in St. Leonard?

Yes, there are holiday rentals close to the most popular sights in St. Leonard, or you can select a more secluded option if you're looking for a relaxing stay. St. Leonard is known for its shopping and sporting events. Make sure you have time to check out the restaurants and wineries during your trip.

What are some of the best holiday rentals that St. Leonard has to offer?

Private 2 Acre Waterfront Family Retreat with Pool & Pier: This holiday home rental outside of St. Leonard is located on the waterfront, and has an outdoor pool, a balcony and a BBQ to put you at ease in your new surroundings. It has 8 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of books.

How many holiday rentals are there in St. Leonard?

With 20 Expedia holiday rentals, you're guaranteed to find just the right place for your St. Leonard stay.

What’s there to see and do in St. Leonard?

Matoaka Beach and Northern Chesapeake Bay are a couple of lovely local spots to get outside and enjoy nature. Other places in town to visit include Patuxent River and Chesapeake Bay.

What’s a holiday rental in St. Leonard like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in St. Leonard. Holiday rentals feature extras like kitchens and laundry facilities so you'll have all the conveniences of home. If you're concerned about a sanitised environment, a holiday rental can offer a sense of security away from public hotel lifts and bustling concierge desks while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a great choice for family trips.

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Our top choices for St. Leonard holiday rentals