St. Leonard Holiday Rentals

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Holiday Rentals in St. Leonard

Welcome to Hickory House on the Chesapeake Bay!
9.6 out of 10, Exceptional, (21)
"The house was perfect for a quiet getaway to relax in. Parking pass available was a bonus since the bay is walking distance. Finding a place to include our puppy made the whole experience worth while."
Welcome to Hickory House on the Chesapeake Bay!
Waterfront house with private beach and pier
9.8 out of 10, Exceptional, (15)
"Peaceful, relaxing, lots of nature with a beautiful home to accompany the experience. We had everything we needed and hated to leave!"
Waterfront house with private beach and pier
Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing
9.8 out of 10, Exceptional, (122)
"Everything was perfect! Having a boat dock in backyard was awesome! Our hosts were awesome and very accommodating! Really didn’t need anything extra! To wake up walk out into screened porch for morning coffee and watch nature was perfect! We will definitely be back! "
Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing
Waterfront Cottage in Beautiful Hoopers Island
10.0 out of 10, Exceptional, (61)
"We can't say enough good things about our long weekend stay! This was our first time in the area, and it was so quiet, peaceful, and beautiful. The views from the home were stunning, and everything was clean, welcoming, and bright—exactly what we needed for a little getaway. My husband and our dogs absolutely loved it. We spent most of our time outdoors, but when we were inside, the home was cozy, warm, and comforting. We slept great every night. The host was communicative and helpful, and we...
Waterfront Cottage in Beautiful Hoopers Island
Cozy Virginia Potomac Riverfront Cottage
9.8 out of 10, Exceptional, (32)
"Communication was prompt. Cottage was clean. The views were spectacular. I would stay again."
Cozy Virginia Potomac Riverfront Cottage
The Schultz Estate
9.2 out of 10, Wonderful, (13)
"What a wonderful stay we had! The house was so comfortable with plenty of space for everyone to relax and enjoy each other's company. We enjoyed the brisk mornings on the porch and the gorgeous sunsets in the evenings. Very comfortable beds and linens. The scenery and landscape in the area are breathtaking. Every turn provided another incredible view of the water. Fishing Creek is close to so many beautiful, quaint towns along the Chesapeake Bay. Highly recommend!"
The Schultz Estate
Beautiful Waterfront Retreat in Cambridge!
10.0 out of 10, Exceptional, (26)
"Great house and location. Very family friendly! "
The price is AU$755
includes taxes & fees
1 Oct - 2 Oct
Beautiful Waterfront Retreat in Cambridge!
Soul Oasis - home on the Chesapeake Bay
9.8 out of 10, Exceptional, (15)
"The private beach is beautiful. Neighborhood is nice and quiet. Enjoyed our stay."
The price is AU$460
includes taxes & fees
1 Oct - 2 Oct
Soul Oasis - home on the Chesapeake Bay
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock
9.8 out of 10, Exceptional, (71)
"We stayed at Saddle House during 2024 Ironman Maryland, with 2 Ironmans competing and lots of support traveling to stay. I was concerned choosing a house about 20 minutes from the start/finish but it was an amazing choice with great bike route access. House is secluded and serene, amazing cleanliness, kitchen with everything you could ever need. Pictures are very accurate to the product you get. Jon was a great help finding things to do, house has incredible resources that support you during...
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
9.8 out of 10, Exceptional, (32)
"Jacob’s home was perfect for our wedding weekend. It had plenty of space for all of our family members. There was more than enough space throughout the house and outside for all of us to relax and enjoy time in. The view of the water is amazing! Hope to come back another time, thank you!"
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
Maryland Vacation Rental w/ Private Pool & Dock
10.0 out of 10, Exceptional, (5)
"We enjoyed our time in Lusby. There was enough room for our family of four. The kitchen was well stocked and it was nice having a gas grill. My husband enjoyed trying to catch fish off the dock. He did manage to get two crabs. We spent most of our time in the pool and relaxing on the deck. The house is located near several grocery stores and restaurants."
Maryland Vacation Rental w/ Private Pool & Dock
Waterfront Relaxing Getaway
9.8 out of 10, Exceptional, (18)
"Nice house, beautiful waterfront property, great host. No complaints whatsoever, highly recommend. "
Waterfront Relaxing Getaway
Bay view from Calvert Cliffs, Solomons Island & State Park nearby
10.0 out of 10, Exceptional, (36)
"We had a great time on vacation. Loved everything about the house - had everything we needed and we really enjoyed exploring the area. "
Bay view from Calvert Cliffs, Solomons Island & State Park nearby
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
10.0 out of 10, Exceptional, (7)
"This house is huge and has lots of different indoor and outdoor gathering spaces so the kids and adults in our group of three families didn’t have to be on top of each other in one living space the whole time. Big firepit area and huge lawn were great, and we enjoyed the kayaks and canoe. There’s a place to buy fresh crabs, oysters, and shrimp very close by, and the house has everything you need for a crab night. The owner was incredibly responsive and kind."
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp
9.8 out of 10, Exceptional, (56)
"Our group of 6 guys who have been friends since elementary school (all 60+ years old now) enjoyed another great annual visit to Cove House. Fish and crabs were biting. Sunsets and rainbows lit up the sky. And good friends reconnected, laughed, and enjoyed being away from the world for a bit. We will be calling again!"
Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp
The Blue Crab Beach House - Free beach passes
10.0 out of 10, Exceptional, (46)
"Very sweet cottage right in the heart of North Beach. Danielle and Harry were wonderful and so responsive to anything we needed. If you’re lucky you’ll get to meet their adorable dogs. We will be back for sure!"
The Blue Crab Beach House - Free beach passes
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!
9.6 out of 10, Exceptional, (14)
"Amazing time with friends and family at this property. I just need to remember to buy more bug spray haha. Regardless though- it was worth it"
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!
Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier
9.8 out of 10, Exceptional, (107)
"What a cool house - awesome views of Chesapeake. private beach, private pier and kayaks! what more can you ask for? Awesome!"
Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier
Waterfront Lusby Retreat w/ Deep-Water Dock & Slip
9.8 out of 10, Exceptional, (10)
"We stayed for a quick weekend during a celebration of life. We enjoyed the ample communal space. Our only complaint was the lack of dog friendly space for potty breaks and there were quite a few things with notes that were broken around the house. "
Waterfront Lusby Retreat w/ Deep-Water Dock & Slip
Private 9 acre Family Retreat on the Chesapeake Bay
10.0 out of 10, Exceptional, (7)
"House was loaded with activities for all ages. So much to do and see. Host was outstanding! Friendly and extremely accommodating."
Private 9 acre Family Retreat on the Chesapeake Bay
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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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Other types of properties in St. Leonard you may be interested in

Welcome to Hickory House on the Chesapeake Bay!
9.6 out of 10, Exceptional, (21)
"The house was perfect for a quiet getaway to relax in. Parking pass available was a bonus since the bay is walking distance. Finding a place to include our puppy made the whole experience worth while."
Welcome to Hickory House on the Chesapeake Bay!
La Quinta Inn & Suites by Wyndham Lexington Park - Patuxent
2.5 star property
7.6 out of 10, Good, (1003)
"Good breakfast, price is good. "
The price is AU$149
includes taxes & fees
3 Oct - 4 Oct
La Quinta Inn & Suites by Wyndham Lexington Park - Patuxent
Rod 'N' Reel Resort
3.0 star property
8.2 out of 10, Very good, (1003)
"Fabulous property . Location, staff, amenities are all excellent. My family returns every year . Highly recommended! "
The price is AU$249
includes taxes & fees
30 Sept - 1 Oct
Rod 'N' Reel Resort
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.

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?

Welcome to Hickory House on the Chesapeake Bay!: This highly rated holiday home rental in St. Leonard is located near the beach, and has a fireplace, a patio and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals are there in St. Leonard?

With 18 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?

Patuxent River and Jefferson Patterson Park and Museum are a couple of lovely local spots to get outside and enjoy nature. In the wider area, you’ll find Perigeaux Vineyards and Winery and Calvert Cliffs State Park.

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.