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

St. Leonard Vacation Rentals

Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

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.
$246 nightly
The price is $261
Oct 6 - Oct 7
Total with taxes and fees
3-bedroom house in soothing Saint Leonard with AC for relaxing stays
A grassy area with a stone path leading to a seating arrangement under trees, overlooking a body of water.

2. 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
9.2 out of 10, Wonderful, (15 reviews)
"Beautiful view from the house. Extremely clean. Had everything we needed. Can't wait to come back"
United States
ed r.
$260 nightly
The price is $287
Oct 4 - Oct 5
Total with taxes and fees
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Pool

3. Family Beach House: Spacious Deck, Grill & Views

Family Beach House: Spacious Deck, Grill & Views
Chesapeak beach
9.2 out of 10, Wonderful, (7 reviews)
"Everything was great. The owner was extremely helpful. Couldn't ask for anything better."
United States
Bryan P.
$436 nightly
The price is $455
Oct 4 - Oct 5
Total with taxes and fees
Family Beach House: Spacious Deck, Grill & Views
A lakeside view with chairs and a table, a rainbow, and trees.

4. Bright and airy waterfront getaway

Bright and airy waterfront getaway
Benedict
9.8 out of 10, Exceptional, (24 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 4 - Oct 5
Total with taxes and fees
Bright and airy waterfront getaway
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.
$281 nightly
The price is $310
Oct 4 - Oct 5
Total with taxes and fees
Beachside Oasis with Beach Passes & King Suite by A Haven Away
A pathway lined with trees and lights leading to a wooden building with a visible window.

6. 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, (14 reviews)
"Nice house in a great location. Great for groups."
United States
Anonymous traveler
$803 nightly
The price is $851
Oct 5 - Oct 6
Total with taxes and fees
Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay
Private kitchen

7. Just a getaway piece of property

Just a getaway piece of property
Mechanicsville
10.0 out of 10, Exceptional, (1 review)
"Perfect place. Just what i was looking. Definitely recommend to anyone looking to stay close to the MIR track for any event"
United States
David L.
$209 nightly
The price is $230
Oct 6 - Oct 7
Total with taxes and fees
Just a getaway piece of property
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.

8. Lakefront Cabin Near Solomons Island w/ Hot Tub

Lakefront Cabin Near Solomons Island w/ Hot Tub
Lusby
10.0 out of 10, Exceptional, (2 reviews)
"Very much enjoyed our stay. The host was very kind and responsive and the property very comfortable. Hot tub and quiet location were great!"
United States
Tanya S.
$1,063 nightly
The price is $1,174
Oct 5 - Oct 6
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.

9. 4-BR Waterfront Turret Home

4-BR Waterfront Turret Home
Solomons
10.0 out of 10, Exceptional, (12 reviews)
"Beautiful house. Beautiful scenery. Everything was perfect. "
United States
Thomas S.
$652 nightly
The price is $720
Oct 4 - Oct 5
Total with taxes and fees
4-BR Waterfront Turret Home
A single-story house with a gabled roof, a front porch, and a small front yard with a flag.

10. Plum Point Cottage #17

Plum Point Cottage #17
Huntingtown
$415 nightly
The price is $458
Oct 3 - Oct 4
Total with taxes and fees
Plum Point Cottage #17
A cozy living room with a large sectional sofa, a round woven coffee table, and a ceiling fan.

11. Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock

Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock
Lusby
10.0 out of 10, Exceptional, (3 reviews)
"We loved our stay! Lovely home, beautiful view"
United States
Sarah R.
$970 nightly
The price is $976
Oct 6 - Oct 7
Total with taxes and fees
Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock
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.

12. Lakefront Cabin Near Solomons Island w/ Hot Tub

Lakefront Cabin Near Solomons Island w/ Hot Tub
3.0 star property
Lusby
$1,062 nightly
The price is $1,179
Oct 5 - Oct 6
Total with taxes and fees
Lakefront Cabin Near Solomons Island w/ Hot Tub
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
$255 nightly
The price is $278
Oct 5 - Oct 6
Total with taxes and fees
Coles Point Marina
An outdoor dining area with string lights, wooden tables, and chairs, overlooking a marina with boats.

14. 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, (37 reviews)
"We enjoyed our stay in North Beach at this lovely residence. It was spacious, clean, nicely furnished and only a few minutes walk to the bay. The beds were so comfortable too!!"
United States
Penny N.
$463 nightly
The price is $511
Oct 14 - Oct 15
Total with taxes and fees
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
A modern kitchen with dark cabinets, a dishwasher, and a countertop with a sink.

15. 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.
$552 nightly
The price is $585
Oct 4 - Oct 5
Total with taxes and fees
Anne & Fred`s Leonardtown Home W/ Arcade room!
A market with a covered seating area and a sign indicating parking for curbside pickup.

16. Rose Haven Coastal Cottage

Rose Haven Coastal Cottage
North Beach
10.0 out of 10, Exceptional, (1 review)
"Great place to stay! Location was nice and close to water views. House was charming and CLEAN. Owners went above and beyond to make the stay welcoming and convenient. Price was reasonable until additional Vrbo fees were added."
United States
Sharon t.
$380 nightly
The price is $433
Oct 4 - Oct 5
Total with taxes and fees
Rose Haven Coastal Cottage
A covered patio with a view of a lake, furnished with chairs and a table.

17. 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, (17 reviews)
"Beautiful sunset and very comfortable rooms. "
United States
Andrea B.
$378 nightly
The price is $381
Oct 20 - Oct 21
Total with taxes and fees
Waterfront Retreat | New Private Pier | Remodeled | Epic Sunset Views
A spacious living room with a large window, a ceiling fan, and a view of the outdoors.

18. 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, (16 reviews)
"very serene, peaceful home on the bay! Amazing getaway! "
United States
Jill C.
$545 nightly
The price is $578
Oct 7 - Oct 8
Total with taxes and fees
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
A kitchen with white cabinets, a stainless steel refrigerator, a microwave, a stove, and a sink.

19. Waterfront Getaway with Dock

Waterfront Getaway with Dock
Woolford
10.0 out of 10, Exceptional, (67 reviews)
"It was perfect for our overnight on way to NY!"
United States
Meagan G.
$263 nightly
The price is $279
Oct 18 - Oct 19
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.

20. 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, (66 reviews)
"Beautiful location "
United States
Jonathan M.
$759 nightly
The price is $838
Oct 26 - Oct 27
Total with taxes and fees
2 Acre Oasis with Private Beach! Family and dog friendly!
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

avid hotel California - Lexington Park by IHG

avid hotel California - Lexington Park by IHG

10/10 Excellent
"Free water from dispenser at breakfast area."
Han 3-night trip
Posted 8 hours ago
avid hotel California - Lexington Park by IHG

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 $261 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.