St. Leonard Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

    Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

    OneKeyCash

    Earn OneKeyCash on all your eligible bookings

    Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Oct 24 - Oct 26
In two months
Dec 5 - Dec 7
In three months
Jan 2 - Jan 4
In four months
Jan 30 - Feb 1

Vacation Rentals in St. Leonard

Summer Getaway ~ Beach Combing & Relaxation
Beach nearby, sun loungers, beach towels

Summer Getaway ~ Beach Combing & Relaxation

9.6 out of 10, Exceptional, (24)
"Host was great to communicate with --- always available if needed, but never intrusive. House was great and had everything we needed. Clean, comfortable, and convenient to the beach. We loved our stay here. Would stay here again."
Summer Getaway ~ Beach Combing & Relaxation
Studio on the Bay.
Beach nearby, beach towels

Studio on the Bay.

10.0 out of 10, Exceptional, (23)
"Everything was fantastic! Clean, well stocked with essentials, and close to the beach. Quiet neighborhood and only 15-20 minutes from many state parks. Great communication from the host throughout our stay. We will be visiting again!"
Studio on the Bay.
NEW: Life on the River! Luxury estate with jacuzzi and private pier!
Property grounds

NEW: Life on the River! Luxury estate with jacuzzi and private pier!

10.0 out of 10, Exceptional, (31)
"Wonderful property and even better hosts! Highly recommend!"
NEW: Life on the River! Luxury estate with jacuzzi and private pier!
Discover tranquility near Calvert Cliffs
Outdoor dining

Discover tranquility near Calvert Cliffs

9.8 out of 10, Exceptional, (16)
"Comfortable beds, large house with awesome views…had a great experience"
Discover tranquility near Calvert Cliffs
Tiny, Funky, and Full of Love - Welcome to the Love Shack
Terrace/patio

Tiny, Funky, and Full of Love - Welcome to the Love Shack

9.8 out of 10, Exceptional, (9)
"This was the perfect spot for my husband and I and our two dogs. The large fenced yard was great to spend time in. The bed and pillows were extremely comfortable. We will definitely be back if we are in the area again! "
Tiny, Funky, and Full of Love - Welcome to the Love Shack
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
Outdoor dining

Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

9.8 out of 10, Exceptional, (47)
"Our large family of adults and two one-year-olds and a dog had a perfect week. The hosts were kind and responsive, and the home was spacious with lots of room for privacy and being all together. Looking forward to going again!"
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay
Dining

Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay

10.0 out of 10, Exceptional, (180)
"Cottage was just as pictured. Lots of character and charm. Host, Brett was easy to work with and very helpful!"
Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay
Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing
Property grounds

Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing

9.8 out of 10, Exceptional, (151)
"The place was great, the host was great,"
Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing
Family and Pet-Friendly, Waterfront with Pier
Exterior

Family and Pet-Friendly, Waterfront with Pier

10.0 out of 10, Exceptional, (259)
"It is a perfect spot to relax and enjoy the water. We will book again if we are back that way. "
Family and Pet-Friendly, Waterfront with Pier
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock
Outdoor pool, a heated pool

Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock

9.8 out of 10, Exceptional, (74)
"We sought a large home for a special family birthday, with multiple bedrooms, roomy eating and living areas, and water access for recreation. This house met all our requirements and more. Our grandchildren, from teen to preschool, loved the multiple kayaks, the crab traps, roasting marshmallows at the fire pit, swimming in the heated pool, finding oyster shells along the shoreline. We visited Annapolis for a sail and sightseeing, even though it meant driving back over the Bay bridge, and we...
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock
El Camino
Terrace/patio

El Camino

10.0 out of 10, Exceptional, (49)
"Great location, the dock is perfect for sunsets, nice balance of waterfront but also cabin vibes"
El Camino
Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp
Exterior

Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp

9.8 out of 10, Exceptional, (75)
"What a great property, wildlife abounds!!! We had a fantastic weekend with family and friends!"
Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp
Bay view from Calvert Cliffs, Solomons Island & State Park nearby
Smart TV, fireplace

Bay view from Calvert Cliffs, Solomons Island & State Park nearby

10.0 out of 10, Exceptional, (55)
"Such a beautiful place to stay. Had absolutely everything you could need. Comfy beds and tons of space. Definitely recommend staying here!"
Bay view from Calvert Cliffs, Solomons Island & State Park nearby
Waterfront Solomons Apartment
Interior

Waterfront Solomons Apartment

9.2 out of 10, Wonderful, (12)
"Very clean, awesome location and amazing hosts!! "
$239 nightly
The price is $253
Oct 8 - Oct 9
Total with taxes and fees
Waterfront Solomons Apartment
Cozy Cottage with access to and partially obstructed views of the bay.
Fridge, microwave, oven, stovetop

Cozy Cottage with access to and partially obstructed views of the bay.

9.0 out of 10, Wonderful, (29)
"Property was cozy and clean. Owners left lights on for us knowing we had a late arrival. Would definitely stay again. "
Cozy Cottage with access to and partially obstructed views of the bay.
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
Exterior detail

Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)

10.0 out of 10, Exceptional, (12)
"Really nice property. Relaxing weekend. Stayed here with my daughter for two nights. We had a great time. "
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
Waterfront Wildlife Retreat on the Patuxent River
Interior

Waterfront Wildlife Retreat on the Patuxent River

10.0 out of 10, Exceptional, (171)
"We went here just for a little weekend getaway for my boyfriend, his brother, his brother’s girlfriend and their kids. We had the absolute best time, such a nice getaway even if it was only for 3 days. The view of the bay from the house is gorgeous and everything was perfect. I will be recommending this stay to anyone I can! "
Waterfront Wildlife Retreat on the Patuxent River
Waterfront Cottage in Beautiful Hoopers Island
Property grounds

Waterfront Cottage in Beautiful Hoopers Island

10.0 out of 10, Exceptional, (79)
"We had a very nice stay and enjoyed the quiet environment and the amenities of the property. Lots of great area for walking. "
Waterfront Cottage in Beautiful Hoopers Island
Potomac Rvr Woodland Cottage, Polite Pets welcomed, Central Air, Stunning Sunset
Terrace/patio

Potomac Rvr Woodland Cottage, Polite Pets welcomed, Central Air, Stunning Sunset

9.8 out of 10, Exceptional, (55)
"We had a wonderful experience and stay at this cute little cottage. Hosts were amazing as well. Cottage has everything you need. Cute decor, plenty of cookware, towels, linens, TV with streaming and comfortable couch. Communication with host was outstanding and easy check-in and check-out. Will definitely stay here again and strongly recommend to others as a place to stay in the area."
Potomac Rvr Woodland Cottage, Polite Pets welcomed, Central Air, Stunning Sunset
Secluded Riverfront Retreat on 100+ Acre Farm in Mechanicsville, WiFi, AC, &More
Smart TV, printers

Secluded Riverfront Retreat on 100+ Acre Farm in Mechanicsville, WiFi, AC, &More

10.0 out of 10, Exceptional, (4)
"My first thought was "gorgeous", when i walked through the door. This was just the weekend I needed. The screened in porch was relaxing. Be ready to take pictures of the sunrise! "
Secluded Riverfront Retreat on 100+ Acre Farm in Mechanicsville, WiFi, AC, &More
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top St. Leonard Hotel Reviews

Holiday Inn Express Prince Frederick by IHG

Holiday Inn Express Prince Frederick by IHG

10/10 Excellent
"Clean comfortable room "
Darren 4-night trip
Posted 6 hours ago
Holiday Inn Express Prince Frederick by IHG

Find out more about St. Leonard

Find out more about St. Leonard

Everything you need to know about St. Leonard vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the St. Leonard vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

St. Leonard vacation 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 low season months. For more hustle and bustle, you may prefer to visit St. Leonard in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $253 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on St. Leonard rentals

At Expedia, we put the best St. Leonard vacation 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 vacation.

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.

Explore a world of travel with Expedia

Explore a world of travel with Expedia

Frequently asked questions

Can I find a vacation rental in St. Leonard?

Yes, we offer vacation rentals close to the most popular points of interest in St. Leonard, or you can choose a more secluded option if you want a relaxing place to 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's the top vacation rental that St. Leonard has to offer?

Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub: Located near St. Leonard, this vacation home rental is located on the waterfront and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a balcony, a garden, and a hot tub so you can immerse yourself in your vacation.

How many vacation rentals are there in St. Leonard?

With 15 Expedia vacation rentals, you're sure to find just the right place for your St. Leonard stay.

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

Matoaka Beach and Flag Ponds Nature Park are a couple of lovely local spots to get outside and enjoy nature. Other places in town to visit include Jefferson Patterson Park and Museum and Patuxent River.

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

Vacation rentals are privately owned properties you can book for a couple of days or more in St. Leonard. Vacation rentals feature extras like laundry facilities and kitchens to help you enjoy your stay. If you're concerned about a clean environment, a vacation rental can provide a sense of security away from shared hotel elevators and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a hotel, which makes a vacation rental a great option for a family trip or a small group gathering.