St. Leonard Holiday Rentals

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

    Change your mind

    Book hotels with free cancellation

    Treat yourself

    Sign in to save 10% or more on thousands of hotels

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Holiday Rentals in St. Leonard

NEW: Life on the River! Luxury estate with jacuzzi and private pier!
10.0 out of 10, Exceptional, (31)
"The Blue Pearl exceeded our expectations. Our stay was pure luxury. The host has thought of every possible amenity from the towel warmer to the kayaks to the gourmet kitchen. Having fresh steamed crab caught that day right off of the dock was a wonderful experience. "
United States
Jason B.
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"
United States
Deborah R.
Discover tranquility near Calvert Cliffs
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."
United States
Holly H.
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!"
United States
Kristin G.
Studio on the Bay.
Walk to Beach: Charming Maryland Home w/ Yard!
3.0 star property
10.0 out of 10, Exceptional, (1)
"This little gem of a house was absolutely perfect! The house was so close to the beach and to all the places we needed to go. We were visiting from Indiana to attend my son and his wife’s baby shower! The hosts had little snacks, coffee, beach towels, etc at the ready. Everything was so clean and comfortable! Definitely give this place a 10/10! "
United States
Tiffany
Walk to Beach: Charming Maryland Home w/ Yard!
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
9.8 out of 10, Exceptional, (50)
"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!"
United States
Lynne J.
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
The Cozy Crab- Your Charming Haven in Lovely North Beach!
9.8 out of 10, Exceptional, (12)
"Great place. Just a short drive to town with shops, restaurants, and boardwalk."
United States
scott
The Cozy Crab- Your Charming Haven in Lovely North Beach!
Tiny, Funky, and Full of Love - Welcome to the Love Shack
10.0 out of 10, Exceptional, (11)
"Such a great accommodation!!! We were here for a swim meet in town and Katie was the greatest host. We had all the comforts and amenities needed. We will def be staying again. "
United States
Joleen H.
Tiny, Funky, and Full of Love - Welcome to the Love Shack
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!"
United States
Michelle R.
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,"
United States
Travis
Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing
Potomac Rvr Woodland Cottage, Polite Pets welcomed, Central Air, Stunning Sunset
9.8 out of 10, Exceptional, (56)
"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."
United States
Mary S.
Potomac Rvr Woodland Cottage, Polite Pets welcomed, Central Air, Stunning Sunset
Waterfront Solomons Apartment
9.2 out of 10, Wonderful, (13)
"Very clean, awesome location and amazing hosts!! "
United States
Jeff R.
The price is AU$419
includes taxes & fees
23 Oct - 24 Oct
Waterfront Solomons Apartment
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...
United States
Ronald S.
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock
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. "
United States
Dara M.
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
Waterfront Wildlife Retreat on the Patuxent River
10.0 out of 10, Exceptional, (172)
"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! "
United States
Nicole V.
Waterfront Wildlife Retreat on the Patuxent River
Family and Pet-Friendly, Waterfront with Pier
10.0 out of 10, Exceptional, (262)
"It is a perfect spot to relax and enjoy the water. We will book again if we are back that way. "
United States
Catherine W.
Family and Pet-Friendly, Waterfront with Pier
Waterfront- 5-bedroom house with dock in charming North Beach
2.0 star property
10.0 out of 10, Exceptional, (2)
"Lovely home with beautiful views of the Bay. Very spacious and well appointed. The hosts were very responsive to our questions. Great place to celebrate our birthdays with all the family including grandkids. Very convenient to North Beach. "
United States
ellen p.
Waterfront- 5-bedroom house with dock in charming North Beach
Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp
9.8 out of 10, Exceptional, (76)
"The property is just as listed! Thoroughly enjoyed the house, the grounds, and the beach! Rick was accommodating and responsive. What a great place!"
United States
David and Ilana X.
Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp
"Point of View" Waterfront cottage with panoramic views on Tilghman Island
10.0 out of 10, Exceptional, (14)
"We had a wonderful stay at the Point of a View Cottage! The views are spectacular and we also enjoyed how easy it was to walk to places to eat and the local market. Recommendations for places to eat were spot on and also appreciated a message over the weekend notifying us of the local craft market held Sunday morning. Would love to come again one day! "
United States
Jennifer L.
"Point of View" Waterfront cottage with panoramic views on Tilghman Island
Belle of the Chesapeake Bay
9.2 out of 10, Wonderful, (16)
"Excellent communication from the owner, Julie and the property manager. Our family (newborn to adults) stayed at this property while in town for a wedding at Rousby Hall. We were a quick and easy 15 minute drive away from the venue. The house was very clean and nicely set up to accommodate our group. We only wish we had more time to spend at the house than we did. The pictures are exactly what you see when you check in - no unhappy surprises. Thank you for hosting us and being so flexible...
United States
eileen b.
Belle of the Chesapeake Bay
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.
Save an average of 15% on thousands of hotels when you're signed in

Top St. Leonard Hotel Reviews

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$419 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?

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 15 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.