St. Leonard Holidays

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Your St. Leonard Holiday

Book a custom holiday package to St. Leonard and prepare to experience this city the way you want. Consider staying in the neighbourhood of Solomons Island, which is good for fishing and a whole lot more. Any trip to St. Leonard needs a well-planned itinerary. Fill yours with famous sights like Jefferson Patterson Park and Museum, Battle Creek Cypress Swamp Sanctuary and Perigeaux Vineyards and Winery. A couple of quick clicks is all it takes to create your dream St. Leonard holiday on Expedia.

St. Leonard Holiday

St. Leonard Essential Information

Language
English
Currency
U.S dollars
Population
740
Max Temp Winter
7ºC
Max Temp Summer
29ºC
Top Sights
Running Hare Vineyard, Jefferson Patterson Park and Museum and Perigeaux Vineyards and Winery

Our pick of the best St. Leonard Hotel Deals

Historic 1825 Chesapeake Farm Stay

Historic 1825 Chesapeake Farm Stay

2 out of 5
1380 Wagner Street St. Leonard MD
The price is AU$254 per night from 16 Dec to 17 Dec
AU$254
16 Dec - 17 Dec
includes taxes & fees
10/10 Exceptional! (6 reviews)
"was a very good experience the house was super cute and very clean the bed was comfy"

Reviewed on 10 Nov 2026

Historic 1825 Chesapeake Farm Stay
Welcome to Hickory House on the Chesapeake Bay!

Welcome to Hickory House on the Chesapeake Bay!

Saint Leonard MD
9.6/10 Exceptional! (22 reviews)
"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 ..."

Reviewed on 29 Sept 2026

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Welcome to Hickory House on the Chesapeake Bay!
Large RENOVATED 6 bedroom 5 bath private home with LOTS of space!

Large RENOVATED 6 bedroom 5 bath private home with LOTS of space!

St Leonard MD
Get rates
Large RENOVATED 6 bedroom 5 bath private home with LOTS of space!
See all 481 properties in St. Leonard
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
All Inclusive Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

Stay near popular St. Leonard attractions

Matoaka Beach

Why not spend a lazy afternoon at Matoaka Beach during your trip to St. Leonard? Amble around the area's parks or visit its shops.
See properties

Frequently asked questions

How much does a St. Leonard holiday package cost?
Offering great value package deals on Expedia, you'll be surprised at how little a holiday to St. Leonard costs! Expedia's packages make travel planning easier and save you more.
What are the cheapest months to go to St. Leonard?
To pick up cheap St. Leonard holiday packages, organise your getaway outside of peak times such as school holidays. You'll typically find better availability and lower prices for flights and hotels.
How many days is enough for St. Leonard?
With a well-organised itinerary, you can easily visit the most popular St. Leonard attractions in a handful of days. But if you want to venture off the beaten track or go on day trips, think about booking your St. Leonard holiday for longer.
How to find the best St. Leonard package deals?
Use Expedia's filter tool to help you find some tempting St. Leonard package deals. When you start your search, simply set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your break for midweek, or look for St. Leonard package deals in the low season. Play around with your travel dates and you may land even bigger discounts. As a rule of thumb, it's usually best to book your holiday package as early as possible.
Is it cheaper to book a St. Leonard holiday as a package?
Expedia holiday packages are designed to help you keep more cash in your pocket. Bundle your hotel, car rental and flight into one great-value price and you could save hundreds of dollars. You'll generally snag a better deal than booking each component separately. And you'll still enjoy the flexibility to create a personalised St. Leonard holiday by choosing your preferred type of stay, airline and car class.
When to book a holiday package to St. Leonard?
Secure incredible discounts by booking your flights ahead of time with Expedia. If spontaneity is more your style, grab one of our last-minute deals for an impromptu St. Leonard getaway.
How to plan a trip to St. Leonard?

  1. Choose when to travel: Check your diary and get your bags packed. Your preferred time of year and the type of activities available will also help you decide when to holiday in St. Leonard.
  2. Figure out your budget: Make sure you have enough money to cover everything from food and transportation to flights and activities. Your hotel will probably be the largest expense during your trip to St. Leonard.
  3. Decide how many days away: Start by listing all the activities and sights you want to get to in St. Leonard. Then, estimate how long you'll need at each, along with any travel time.
  4. Combine your airfare and accommodation: Once you've nailed down your dates and duration, book the ideal St. Leonard holiday package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.