Holiday Rentals in St. Leonard

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Holiday Rentals in St. Leonard

Our top choices for St. Leonard holiday rentals

New! Cozy River Cottage with great views of the water!

9.6 out of 10, Exceptional, (9)
"A very nice house with an amazing view 10/10 recommend"
New! Cozy River Cottage with great views of the water!

WATERFRONT!!! The River's Roost on The Patuxent River

10.0 out of 10, Exceptional, (29)
"We had an amazing stay in this beautiful house! Inside was massive perfectly set up for our needs. Outside had stunning views and there is nothing better than being on the waters edge. The owners were easy to communicate with and they had everything ready in a timely manner for our check in. We didn’t get a chance to catch any crabs but we will definitely stay here again to try our hand at that."
WATERFRONT!!! The River's Roost on The Patuxent River

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

Cottage on the Bay

8.0 out of 10, Very good, (2)
"We had a wonderful visit! The cottage was exceptionally equipped with towels, kitchen, beach chairs, wood for the fire pit, ect. "
Cottage on the Bay

Summer Getaway ~ Beach Combing & Relaxation

9.4 out of 10, Exceptional, (23)
"We just loved the house! Private Beach is beautiful! Will definitely stay again! "
Summer Getaway ~ Beach Combing & Relaxation

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

10.0 out of 10, Exceptional, (50)
"Awesome home wnd location! Would stay again!"
Bay view from Calvert Cliffs, Solomons Island & State Park nearby

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

10.0 out of 10, Exceptional, (178)
"The views are fantastic. Very quiet neighborhood. "
Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay

Family and Pet-Friendly, Waterfront with Pier

10.0 out of 10, Exceptional, (255)
"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

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

9.8 out of 10, Exceptional, (46)
"Beautiful views and a lush backyard. Jacob was excellent with communication. The house was clean and had all amenities needed for a wonderful stay. Please note there are a lot of stairs in the house as well as get to the dock. It was a good workout for us!"
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

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

10.0 out of 10, Exceptional, (4)
"The place had everything we needed and the yard was great for the dogs. Would definitely stay here again."
Tiny, Funky, and Full of Love - Welcome to the Love Shack

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

9.8 out of 10, Exceptional, (143)
"We stayed here for the weekend while attending a car show at the raceway close by. Very private and welcoming. Great place to relax and unwind after a long day. "
Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing

Waterfront Solomons Apartment

9.6 out of 10, Exceptional, (11)
"We really enjoyed our stay on Solomon’s Island. The apartment was the perfect location to enjoy the island’s amenities. The bed was really comfortable and shower great. The view from the living room was spectacular. "
The price is €265
includes taxes & fees
5 Sept - 6 Sept
Waterfront Solomons Apartment

The Cozy Crab- Your Charming Haven in Lovely North Beach!

9.4 out of 10, Exceptional, (6)
"Modern, Fresh, Clean! No complaints at all!"
The Cozy Crab- Your Charming Haven in Lovely North Beach!

Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE

10.0 out of 10, Exceptional, (7)
"Lovely little rustic cottage full of charm.We arrived over Thanksgiving,the off season was wonderful thank s again"
Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE

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

9.8 out of 10, Exceptional, (70)
"We enjoyed the property lots of wildlife around enjoyed kayaking and crabing . "
Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp

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

9.8 out of 10, Exceptional, (73)
"We had a wonderful stay including boating, kayaking, swimming, fishing, campfires and crabs! The house was perfect for our group and the owner was very accommodating."
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock

Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.

9.6 out of 10, Exceptional, (4)
"Just the perfect place I needed for a personal retreat. It is quiet, peaceful and serene. I would definitely visit again. "
The price is €263
includes taxes & fees
21 Aug - 22 Aug
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.

Waterfront Cottage in Beautiful Hoopers Island

10.0 out of 10, Exceptional, (76)
"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

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

10.0 out of 10, Exceptional, (7)
"Perfect house for a long weekend. Clean, cozy and great communication with Maxine. Would definitely stay here again when I return to Cambridge. "
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)

Maryland Vacation Rental w/ Private Pool & Dock

9.2 out of 10, Wonderful, (12)
"We needed a house for a quick stay in Lusby. The hosts have thought of everything to make the stay easy. They communicated ahead of our trip and were easy to work with. "
Maryland Vacation Rental w/ Private Pool & Dock
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

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?

New! Cozy River Cottage with great views of the water!: This highly rated holiday home rental in St. Leonard is located on a river, and has a garden, a BBQ and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave.

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.