St. Leonard Holiday Rentals

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Holiday Rentals in St. Leonard

Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
9.6 out of 10, Exceptional, (5)
"Just the perfect place I needed for a personal retreat. It is quiet, peaceful and serene. I would definitely visit again. "
The price is AU$466
includes taxes & fees
17 Oct - 18 Oct
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Soul Oasis - home on the Chesapeake Bay
9.8 out of 10, Exceptional, (35)
"Lovely house with tons of character. Clean and comfortable. A few steps from water. "
The price is AU$484
includes taxes & fees
22 Oct - 23 Oct
Soul Oasis - home on the Chesapeake Bay
Riverside Dreams -golfcart-views-screened porch-
2.0 star property
10.0 out of 10, Exceptional, (3)
"We found the view and the accommodations quite lovely."
The price is AU$582
includes taxes & fees
22 Oct - 23 Oct
Riverside Dreams -golfcart-views-screened porch-
Cottage Located on the Patuxent River!
10.0 out of 10, Exceptional, (42)
"The accommodations were superb and being on the water was amazing!"
The price is AU$548
includes taxes & fees
4 Nov - 5 Nov
Cottage Located on the Patuxent River!
Waterfront Solomons Apartment
9.2 out of 10, Wonderful, (13)
"Very clean, awesome location and amazing hosts!! "
The price is AU$403
includes taxes & fees
18 Oct - 19 Oct
Waterfront Solomons Apartment
Charming 2-bedroom 1 bath cottage with AC, WiFi in peaceful North Beach, Md.
2.0 star property
The price is AU$433
includes taxes & fees
3 Nov - 4 Nov
Charming 2-bedroom 1 bath cottage with AC, WiFi in peaceful North Beach, Md.
Beautiful Waterfront Retreat in Cambridge!
10.0 out of 10, Exceptional, (47)
"Property was as listed. We enjoyed are stay."
The price is AU$621
includes taxes & fees
23 Oct - 24 Oct
Beautiful Waterfront Retreat in Cambridge!
Walk to Beach! King Bed & Free Beach Passes
10.0 out of 10, Exceptional, (16)
"We loved our stay! The property was just as advertised and had everything we needed. Quiet area and felt very safe. The owners provided excellent communication as well!"
The price is AU$597
includes taxes & fees
28 Oct - 29 Oct
Walk to Beach! King Bed & Free Beach Passes
The Hidaway on the Patuxent River<br>Children allowed and welcomed to stay.
9.2 out of 10, Wonderful, (9)
"Got to go fishing, kayaking, and swimming in the pool. Had a great time, views are wonderful and it’s a peaceful environment. 10/10 would stay again."
The price is AU$857
includes taxes & fees
17 Oct - 18 Oct
The Hidaway on the Patuxent River<br>Children allowed and welcomed to stay.
Waterfront Escape | Family-Friendly | Remodeled Home | Epic Sunset Views | Decks
10.0 out of 10, Exceptional, (3)
"Everything was very clean and well put together. Loved the view!"
The price is AU$596
includes taxes & fees
13 Nov - 14 Nov
Waterfront Escape | Family-Friendly | Remodeled Home | Epic Sunset Views | Decks
Modern Waterfront Home with Kayak, Firepit, Gameroom, Pool+Beaches, Dog & EV OK
10.0 out of 10, Exceptional, (4)
"They thought of everything. I would definitely come back for another stay."
The price is AU$695
includes taxes & fees
21 Oct - 22 Oct
Modern Waterfront Home with Kayak, Firepit, Gameroom, Pool+Beaches, Dog & EV OK
Cozy centrally located studio with WiFi and AC in peaceful Port Republic, MD
9.4 out of 10, Exceptional, (6)
"Great place to stay"
The price is AU$275
includes taxes & fees
21 Oct - 22 Oct
Cozy centrally located studio with WiFi and AC in peaceful Port Republic, MD
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
10.0 out of 10, Exceptional, (30)
"Absolutely beautiful and spacious home perfectly located in North Beach. Very peaceful area and close to the beach, restaurants and shopping. We really enjoyed our stay and hope to visit again in the future. "
The price is AU$779
includes taxes & fees
19 Oct - 20 Oct
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
Tranquil Modern Farmhouse
9.4 out of 10, Exceptional, (6)
"This property was super gorgeous and spacious so we were able to relax. Guests had more than enough space and didn’t feel like they were on top of each other sleeping wise! We were able to just have dinner and feel safe! The owner answered any questions we had within 15 minutes, which was super helpful! "
The price is AU$821
includes taxes & fees
27 Oct - 28 Oct
Tranquil Modern Farmhouse
Waterfront Getaway with Dock
10.0 out of 10, Exceptional, (51)
"Great location with everything you may need. It is close to restaurants and Emily’s produce.2nd time staying and will be back again. "
The price is AU$433
includes taxes & fees
16 Nov - 17 Nov
Waterfront Getaway with Dock
Beach Front, Bay View, Fishing, chesapeake,Family Getaway
9.0 out of 10, Wonderful, (6)
"Everything was great. The owner was extremely helpful. Couldn't ask for anything better."
The price is AU$741
includes taxes & fees
16 Nov - 17 Nov
Beach Front, Bay View, Fishing, chesapeake,Family Getaway
Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.
9.4 out of 10, Exceptional, (3)
"We had a short stay after a sporting event in DC, it was a little less than an hour away. Convenient location and a very clean house. Kitchen was well stocked. There was little communication with the owner, which was nice vs a long list of rules, but we would have liked to know any of their local specific favorite spots or more detailed check in/check out. Worked out nicely for our family. "
The price is AU$638
includes taxes & fees
3 Nov - 4 Nov
Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
10.0 out of 10, Exceptional, (14)
"Second time staying at this lovely, serene home/property. It’s the perfect getaway if you’re looking to escape into some peace! Highly recommend "
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!
10.0 out of 10, Exceptional, (7)
"Clean and easy "
The price is AU$576
includes taxes & fees
26 Oct - 27 Oct
2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!
Anne & Fred`s Leonardtown Home W/ Arcade room!
9.2 out of 10, Wonderful, (5)
"Nice place to stay. Perfect location for our needs. Suggest noting the hot and cold water flip upstairs, and to add a mirror in the hallway by outlet for blow dryer."
The price is AU$854
includes taxes & fees
28 Oct - 29 Oct
Anne & Fred`s Leonardtown Home W/ Arcade room!
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

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$403 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.