St. Leonard Holiday Rentals

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Holiday Rentals in St. Leonard

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.

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!

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

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

9.8 out of 10, Exceptional, (8)
Tiny, Funky, and Full of Love - Welcome to the Love Shack

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

10.0 out of 10, Exceptional, (179)
"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

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

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

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

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

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

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

9.2 out of 10, Wonderful, (12)
"Very clean, awesome location and amazing hosts!! "
The price is NZ$434
includes taxes & fees
8 Oct - 9 Oct
Waterfront Solomons Apartment

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)

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

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

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

Waterfront Cottage with Pier & Boatlift on the Beautiful Potomac River

10.0 out of 10, Exceptional, (18)
"Great place! "
Waterfront Cottage with Pier & Boatlift on the Beautiful Potomac River

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

10.0 out of 10, Exceptional, (3)
"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.
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Top St. Leonard Hotel Reviews

Find out more about St. Leonard

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 favorite 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 depends 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 NZ$434 per night. Entering your travel dates in the search wizard you might find 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?

Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub: This holiday home rental outside of St. Leonard is located on the waterfront, and has an outdoor pool, a fireplace and a BBQ 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 that you can cook with friends or family. It offers a balcony, a garden and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals are there in St. Leonard?

With 14 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 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 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.