St. Leonard Vacation Rentals

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Check prices for these dates

Tonight
Jun 22 - Jun 23
Tomorrow
Jun 23 - Jun 24
Next weekend
Jun 27 - Jun 29
In two weeks
Jul 4 - Jul 6

Vacation Rentals in St. Leonard

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

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

9.8 out of 10, Exceptional, (7)
"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
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (22)
"Great stay, beautiful spot. We will be back for sure."
WATERFRONT!!! The River's Roost on The Patuxent River
Waterfront Wildlife Retreat on the Patuxent River
Interior

Waterfront Wildlife Retreat on the Patuxent River

10.0 out of 10, Exceptional, (164)
"The Waterfront Retreat on the Patuxent River is better than advertised. Our whole family stayed -- everyone loved it! It was clean, comfortable, with everything needed to stay comfortably, sleep, eat, relax and use as a home base for exploring. Solomons Island and the surrounding area was filled with lots of fun things to do (restaurant's, museums, history, boating, walking, etc.). "
Waterfront Wildlife Retreat on the Patuxent River
Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing
Property grounds

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

9.8 out of 10, Exceptional, (135)
"Lovely, quiet, clean and comfy "
Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing
The Blue Crab Beach House - Free beach passes
Exterior detail

The Blue Crab Beach House - Free beach passes

10.0 out of 10, Exceptional, (60)
"The property was well- maintained and the kitchen was well-equipped for our needs. Short walk to North Beach for dining and Boardwalk strolls. Nice and toasty for our winter stay - really enjoyed the trip."
The Blue Crab Beach House - Free beach passes
Family and Pet-Friendly, Waterfront with Pier
Exterior

Family and Pet-Friendly, Waterfront with Pier

10.0 out of 10, Exceptional, (248)
"Our stay was great and Rob and Clarissa were very welcoming!"
Family and Pet-Friendly, Waterfront with Pier
Waterfront Cottage in Beautiful Hoopers Island
Fridge, microwave, oven, stovetop

Waterfront Cottage in Beautiful Hoopers Island

10.0 out of 10, Exceptional, (72)
"This is a small, sweet, comfortable cottage, and was just perfect for our brief getaway from the hurly-burly. The house is very well equipped, especially the kitchen, so cooking the local seafood was easy. The decor (loved the faux fireplace) was charming and welcoming, down to the live Poinsettia plant on the table when we got there. "
Waterfront Cottage in Beautiful Hoopers Island
Belle of the Chesapeake Bay
Smart TV

Belle of the Chesapeake Bay

9.2 out of 10, Wonderful, (12)
"This was a great place to stay in a quiet neighborhood, a short drive from Calvert Cliffs State Park. Plenty of space for four adults. We could have stayed longer and would not hesitate to book again."
Belle of the Chesapeake Bay
Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE
Property grounds

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

10.0 out of 10, Exceptional, (5)
"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 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
Outdoor dining

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

9.8 out of 10, Exceptional, (40)
"Beautiful, spacious, the highlight was the view of the bay. Definitely will be back"
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
Bay view from Calvert Cliffs, Solomons Island & State Park nearby
Smart TV, fireplace

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

10.0 out of 10, Exceptional, (43)
"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
Dining

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

10.0 out of 10, Exceptional, (176)
"Great time!! Floridians playing in the snow!! Cozy fire afterwards in the fireplace. Picturesque drive up to the Navy Cabin, deer playing in the snow too."
Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay
Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.
Outdoor pool

Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.

10.0 out of 10, Exceptional, (44)
"We had a great stay! Thanks."
Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.
Huge Beach Bungalow w/Yard, Beach Passes, 2 King Bds near Boardwalk, Restaurants
Outdoor dining

Huge Beach Bungalow w/Yard, Beach Passes, 2 King Bds near Boardwalk, Restaurants

10.0 out of 10, Exceptional, (26)
"Everything about our stay was wonderful..the hosts were so quick to respond to any questions amd were very patient with me with all of my questions..I would DEFINITELY stay here again!!"
Huge Beach Bungalow w/Yard, Beach Passes, 2 King Bds near Boardwalk, Restaurants
Kick back and enjoy the Chesapeake & this 3-bedroom, calm, stylish space.
3 bedrooms, iron/ironing board, WiFi, bed sheets

Kick back and enjoy the Chesapeake & this 3-bedroom, calm, stylish space.

10.0 out of 10, Exceptional, (1)
"We stayed here for 2 nights with 3 other couples. Bedrooms are very spacious. There are 2 rollaway beds and it looks like a pack n play as well for families with kids. Both couches pull out into beds. Everything was perfect for our needs. You can fit 3 cars in the front driveway but there’s also 2 spots available behind the house. You can also see the Bay from the front windows. Close to stores and gas as well. Would definitely recommend! "
Kick back and enjoy the Chesapeake & this 3-bedroom, calm, stylish space.
Waterfront Relaxing Getaway
Fridge, microwave, oven, stovetop

Waterfront Relaxing Getaway

9.8 out of 10, Exceptional, (19)
"We enjoyed our stay. Beautiful spot on the water. House had everything we needed and plenty of space for my family."
Waterfront Relaxing Getaway
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
Smart TV, books, printers

The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

9.8 out of 10, Exceptional, (10)
"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
Beautiful Waterfront Retreat in Cambridge!
Interior

Beautiful Waterfront Retreat in Cambridge!

10.0 out of 10, Exceptional, (37)
"The house was so cute and the fact that we were able to do early check in was amazing!"
The price is ￥42,731
￥76,731 total
includes taxes & fees
Jun 29 - Jun 30
Beautiful Waterfront Retreat in Cambridge!
Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier
Interior

Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier

10.0 out of 10, Exceptional, (116)
"Clean and spacious. Great views! Loved the beach! Found a bunch of fossils. Enjoyed kayaking. Overall outstanding!"
Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier
Sea Glass Beach House! Large sand beach, dock and hot tub! Pets welcome!
Property grounds

Sea Glass Beach House! Large sand beach, dock and hot tub! Pets welcome!

10.0 out of 10, Exceptional, (23)
"Great stay, easy check-in/check-out, highly recommend"
Sea Glass Beach House! Large sand beach, dock and hot tub! Pets welcome!
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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Frequently asked questions

Can I find a vacation rental in St. Leonard?

Yes, we offer vacation rentals close to the most popular points of interest in St. Leonard, or you can choose a more secluded option if you want a relaxing place to 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's the top vacation rental that St. Leonard has to offer?

New! Cozy River Cottage with great views of the water!: Visitors give good reviews to this St. Leonard vacation home rental, which is located on a river and has a garden, a hot tub, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave.

How many vacation rentals are there in St. Leonard?

With 14 Expedia vacation rentals, you're sure to find just the right place for your St. Leonard stay.

What’s there to see and do in St. Leonard?

Matoaka Beach and Patuxent River 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 Flag Harbor Marina.

What’s a vacation rental in St. Leonard like?

Vacation rentals are privately owned properties you can book for a couple of days or more in St. Leonard. Vacation rentals feature extras like laundry facilities and kitchens to help you enjoy your stay. If you're concerned about a clean environment, a vacation rental can provide a sense of security away from shared hotel elevators and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a hotel, which makes a vacation rental a great option for a family trip or a small group gathering.