St. Leonard Holidays

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Top hotels in St. Leonard

Historic 1825 Chesapeake Farm Stay

Historic 1825 Chesapeake Farm Stay

1380 Wagner Street St. Leonard MD
Fully refundableReserve now, pay when you stay
S$165
24 Sept - 25 Sept
includes taxes & fees
10/10 Exceptional! (2 reviews)
"I booked a weekend stay here for my wife and I for our 30th anniversary. The house was amazing. There has been a lot of effort put into its decor which adds plenty of character to this historic hosue.Its very warm and welcoming. We were greeted by Holly upon our arrival she made us feel comfortable ..."

Reviewed on 14 Sept, 2026

Historic 1825 Chesapeake Farm Stay
Rod 'N' Reel Resort

Rod 'N' Reel Resort

4165 Mears Ave Chesapeake Beach MD
Fully refundableReserve now, pay when you stay
S$243
7 Oct - 8 Oct
includes taxes & fees
8.6/10 Excellent! (1,009 reviews)
"Me and my husband loved it. It was great., and for the most part pretty clean, but there was random hairs in our shower and glitter on the bathroom floor when we arrived. I didn’t complain to staff because overall, it was fairly clean. But all the other amenities and the resort as a whole is an excellent ..."

Reviewed on 19 Sept, 2026

Rod 'N' Reel Resort
avid hotel California - Lexington Park by IHG

avid hotel California - Lexington Park by IHG

23274 Three Notch Road California MD
Fully refundable
S$137
1 Oct - 2 Oct
includes taxes & fees
avid hotel California - Lexington Park by IHG
See all 491 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.

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.
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Jefferson Patterson Park and Museum

You can spend time exploring the galleries in Jefferson Patterson Park and Museum during your travels in St. Leonard. Amble around this family-friendly area's riverfront or attend a sporting event.
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Long Beach

Why not spend a lazy afternoon at Long Beach during your trip to Calvert Beach-Long Beach?
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Flag Harbor Marina

Explore the waterfront in Calvert Beach-Long Beach with a trip to Flag Harbor Marina.
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Perigeaux Vineyards and Winery

4.0/10 (2 reviews)
You can enjoy a tasting or tour at Perigeaux Vineyards and Winery during your travels to St. Leonard. Amble around this family-friendly area's riverfront or attend a sporting event.
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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.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.