A beach at sunset with a wooden fence in the background.

St. Leonard Vacation Rentals

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Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for St. Leonard vacation rentals

A bedroom with a bed, a fireplace, a ceiling fan, and a painting of a beach.

1. 3-bedroom house in soothing Saint Leonard with AC for relaxing stays

3-bedroom house in soothing Saint Leonard with AC for relaxing stays
Saint Leonard
10.0 out of 10, Exceptional, (8 reviews)
"Loved the location and the hosts' kindness and care."
United States
Nancy P.
$261 nightly
The price is $277
Oct 26 - Oct 27
Total with taxes and fees
3-bedroom house in soothing Saint Leonard with AC for relaxing stays
A lakeside view with chairs and a table, a rainbow, and trees.

2. Bright and airy waterfront getaway

Bright and airy waterfront getaway
Benedict
9.8 out of 10, Exceptional, (26 reviews)
"Amazing host and home, great view with the water right there, and short drive to any shopping needs. It was the serene getaway I needed to recharge from city life and corporate burnout."
United States
George
$361 nightly
The price is $383
Oct 22 - Oct 23
Total with taxes and fees
Bright and airy waterfront getaway
A modern kitchen with a central island, stainless steel appliances, and a window with butterfly decals.

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

The Cozy Crab- Your Charming Haven in Lovely North Beach!
North Beach
9.6 out of 10, Exceptional, (30 reviews)
"Wonderful place to visit "
United States
James L.
$291 nightly
The price is $308
Oct 22 - Oct 23
Total with taxes and fees
The Cozy Crab- Your Charming Haven in Lovely North Beach!
An outdoor dining area with string lights, wooden tables, and chairs, overlooking a marina with boats.

4. Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
North Beach
10.0 out of 10, Exceptional, (40 reviews)
"This property and host were excellent. Property was as advertised. Lovely, clean, quiet and comfortable. Owner was super responsive and check in and check out was easy. 100% recommend."
United States
Sarah
$419 nightly
The price is $451
Oct 25 - Oct 26
Total with taxes and fees
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
A beach with a rocky shoreline, a swimming area, and multi-story buildings in the background.

5. Beachside Oasis with Beach Passes & King Suite by A Haven Away

Beachside Oasis with Beach Passes & King Suite by A Haven Away
North Beach
10.0 out of 10, Exceptional, (24 reviews)
"Cute, family friendly home. Had everything we needed for a comfortable stay."
United States
Johanna S.
$302 nightly
The price is $325
Oct 23 - Oct 24
Total with taxes and fees
Beachside Oasis with Beach Passes & King Suite by A Haven Away
A grassy area with a stone path leading to a seating arrangement under trees, overlooking a body of water.

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

Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Benedict
9.0 out of 10, Wonderful, (16 reviews)
"Beautiful view from the house. Extremely clean. Had everything we needed. Can't wait to come back"
United States
ed r.
$251 nightly
The price is $277
Oct 22 - Oct 23
Total with taxes and fees
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
A kitchen with white cabinets, a stainless steel refrigerator, a microwave, a stove, and a sink.

7. Waterfront Getaway with Dock

Waterfront Getaway with Dock
Woolford
10.0 out of 10, Exceptional, (68 reviews)
"It was perfect for our overnight on way to NY!"
United States
Meagan G.
$237 nightly
The price is $251
Oct 25 - Oct 26
Total with taxes and fees
Waterfront Getaway with Dock
A modern kitchen with granite countertops, stainless steel appliances, and large windows offering views of the outdoors.

8. 2 Acre Oasis with Private Beach! Family and dog friendly!

2 Acre Oasis with Private Beach! Family and dog friendly!
Leonardtown
10.0 out of 10, Exceptional, (67 reviews)
"Everything about this property is wonderful for our family! A dreamy relaxing vacation"
United States
Carol L.
$767 nightly
The price is $847
Oct 26 - Oct 27
Total with taxes and fees
2 Acre Oasis with Private Beach! Family and dog friendly!
A room with a large window overlooking a beach with a wooden pier and lounge chairs.

9. Cozy Virginia Potomac Riverfront Cottage

Cozy Virginia Potomac Riverfront Cottage
Hague
9.6 out of 10, Exceptional, (56 reviews)
"This is our 4th time to come here and the view still amaze me. Fishing is great in this area. My family and I really had an amazing, fun and relaxing stay as always. See you next time."
United States
Natt L.
$315 nightly
The price is $343
Oct 22 - Oct 23
Total with taxes and fees
Cozy Virginia Potomac Riverfront Cottage
A covered outdoor dining area with a table and chairs, overlooking a body of water and trees.

10. Sunset Breezes - quiet waterfront retreat

Sunset Breezes - quiet waterfront retreat
Dorchester County
10.0 out of 10, Exceptional, (45 reviews)
"Comfortable, roomy, awesome views!"
United States
John C.
$291 nightly
The price is $321
Nov 17 - Nov 18
Total with taxes and fees
Sunset Breezes - quiet waterfront retreat
Three Adirondack chairs facing a beach with a clear view of the ocean.

11. Plum Point Cottage #14

Plum Point Cottage #14
Huntingtown
9.8 out of 10, Exceptional, (9 reviews)
"we had a great stay at this property for an impromptu weekend getaway. "
United States
Yonnick H.
$493 nightly
The price is $544
Oct 22 - Oct 23
Total with taxes and fees
Plum Point Cottage #14
A covered patio with a view of a lake, furnished with chairs and a table.

12. Waterfront Retreat | New Private Pier | Remodeled | Epic Sunset Views

Waterfront Retreat | New Private Pier | Remodeled | Epic Sunset Views
Lexington Park
10.0 out of 10, Exceptional, (18 reviews)
"Beautiful sunset and very comfortable rooms. "
United States
Andrea B.
$406 nightly
The price is $409
Oct 27 - Oct 28
Total with taxes and fees
Waterfront Retreat | New Private Pier | Remodeled | Epic Sunset Views
A single-story house with a front porch, a small deck, and a number '4' on the side.

13. Coles Point Marina

Coles Point Marina
2.0 star property
Hague
10.0 out of 10, Exceptional, (1 review)
"If you want a quiet slice of VA/Potomac waterfront, this is the place."
United States
John
$255 nightly
The price is $278
Oct 22 - Oct 23
Total with taxes and fees
Coles Point Marina
A spacious living room with a large TV, blue sofa, and a ceiling fan.

14. The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
Woolford
9.6 out of 10, Exceptional, (35 reviews)
"Beautiful piece of property and clean, comfortable accommodations! Would definitely return if plan to be in that area again!!"
United States
Joyce F.
$642 nightly
The price is $680
Oct 26 - Oct 27
Total with taxes and fees
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
A pathway lined with trees and lights leading to a wooden building with a visible window.

15. Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay

Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay
Lusby
9.6 out of 10, Exceptional, (15 reviews)
"Nice house in a great location. Great for groups."
United States
Anonymous traveler
$803 nightly
The price is $851
Oct 22 - Oct 23
Total with taxes and fees
Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay
A modern kitchen with dark cabinets, a dishwasher, and a countertop with a sink.

16. Anne & Fred`s Leonardtown Home W/ Arcade room!

Anne & Fred`s Leonardtown Home W/ Arcade room!
Leonardtown
9.2 out of 10, Wonderful, (7 reviews)
"Amazing place to stay. Very Very clean ! Great location. Definitely will book this place again "
United States
Christy C.
$548 nightly
The price is $581
Oct 25 - Oct 26
Total with taxes and fees
Anne & Fred`s Leonardtown Home W/ Arcade room!
A spacious living room with a large window, a ceiling fan, and a view of the outdoors.

17. WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
Cambridge
10.0 out of 10, Exceptional, (17 reviews)
"very serene, peaceful home on the bay! Amazing getaway! "
United States
Jill C.
$484 nightly
The price is $513
Oct 27 - Oct 28
Total with taxes and fees
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
A spacious cabin interior with a wooden ceiling, a kitchen area, a living room with a sofa and a dining table, and a large window providing natural light.

18. Lakefront Cabin Near Solomons Island w/ Hot Tub

Lakefront Cabin Near Solomons Island w/ Hot Tub
3.0 star property
Lusby
$1,068 nightly
The price is $1,185
Oct 22 - Oct 23
Total with taxes and fees
Lakefront Cabin Near Solomons Island w/ Hot Tub
A spacious living room with a large sofa, a television, and a view of the ocean.

19. 4-BR Waterfront Turret Home

4-BR Waterfront Turret Home
Solomons
10.0 out of 10, Exceptional, (13 reviews)
"Beautiful house. Beautiful scenery. Everything was perfect. "
United States
Thomas S.
$633 nightly
The price is $700
Oct 25 - Oct 26
Total with taxes and fees
4-BR Waterfront Turret Home
A two-story house with a balcony, surrounded by trees and a wooden fence.

20. Charming Waterfront 3-bedroom house in Piney Point

Charming Waterfront 3-bedroom house in Piney Point
Piney Point
10.0 out of 10, Exceptional, (7 reviews)
"This property was perfect for our night visiting St. Mary's! Spacious, right on the water, and quiet. Thank you!"
United States
Meira
$681 nightly
The price is $752
Oct 30 - Oct 31
Total with taxes and fees
Charming Waterfront 3-bedroom house in Piney Point
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

Sleep Inn & Suites California MD

Sleep Inn & Suites California MD

10/10 Excellent
"Wonderful place for my children and me in my time of need."
Shervon 5-night trip
Posted 9 hours ago
Sleep Inn & Suites California MD

Find out more about St. Leonard

Everything you need to know about St. Leonard vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the St. Leonard vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

St. Leonard vacation 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 low season months. For more hustle and bustle, you may prefer to visit St. Leonard in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $277 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on St. Leonard rentals

At Expedia, we put the best St. Leonard vacation 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 vacation.

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.

Explore a world of travel with Expedia

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?

Private 2 Acre Waterfront Family Retreat with Pool & Pier: This vacation home rental near St. Leonard is located on the waterfront and has an outdoor pool, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 8 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of books.

How many vacation rentals are there in St. Leonard?

With 20 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 Northern Chesapeake Bay are a couple of lovely local spots to get outside and enjoy nature. Other places in town to visit include Patuxent River and Chesapeake Bay.

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.