St. Leonard Vacation Rentals from CA $111: Short-Term Rentals for 2026

Q: 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.

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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

Saint Leonard

Nancy P.

CA $332 total

includes taxes & fees

Nov 16 - Nov 17

A spacious living room with a grey sectional sofa, a round wooden coffee table, and a patterned rug.

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

Prince Frederick

Sean B.

CA $562 total

includes taxes & fees

Nov 20 - Nov 21

A grassy area with a stone path leading to a seating arrangement under trees, overlooking a body of water.

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

Benedict

ed r.

CA $376 total

includes taxes & fees

Nov 12 - Nov 13

4. Plum Point Cottage #14

Huntingtown

Yonnick H.

CA $762 total

includes taxes & fees

Nov 11 - Nov 12

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.

5. Lakefront Cabin Near Solomons Island w/ Hot Tub

Lusby

CA $1,616 total

includes taxes & fees

Nov 12 - Nov 13

6. Plum Point Cottage #15

Maryland

CA $802 total

includes taxes & fees

Nov 11 - Nov 12

7. Plum Point Cottage #17

Huntingtown

CA $645 total

includes taxes & fees

Nov 11 - Nov 12

A triangular cabin with a wooden staircase leading to a door, surrounded by trees.

8. Soul Oasis - home on the Chesapeake Bay

Lusby

Dusty S.

CA $422 total

includes taxes & fees

Nov 18 - Nov 19

A lakeside view with chairs and a table, a rainbow, and trees.

9. Bright and airy waterfront getaway

Benedict

George

CA $516 total

includes taxes & fees

Nov 18 - Nov 19

A pathway lined with trees and lights leading to a wooden building with a visible window.

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

Lusby

Anonymous traveller

CA $1,103 total

includes taxes & fees

Nov 21 - Nov 22

11. Lakefront Cabin Near Solomons Island w/ Hot Tub

Lusby

Tanya S.

CA $1,530 total

includes taxes & fees

Nov 12 - Nov 13

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

Chesapeak beach

Ben W.

CA $567 total

includes taxes & fees

Dec 7 - Dec 8

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

North Beach

Johanna S.

CA $423 total

includes taxes & fees

Nov 12 - Nov 13

A modern kitchen with a central island, stainless steel appliances, and a window with butterfly decals.

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

North Beach

James L.

CA $442 total

includes taxes & fees

Nov 12 - Nov 13

A cozy living room with a large sectional sofa, a round woven coffee table, and a ceiling fan.

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

Lusby

Dani B.

CA $1,312 total

includes taxes & fees

Dec 2 - Dec 3

A spacious living room with a large sofa, a television, and a view of the ocean.

16. 4-BR Waterfront Turret Home

Solomons

Thomas S.

CA $1,001 total

includes taxes & fees

Nov 12 - Nov 13

A single-story house with a front porch, a small deck, and a number '4' on the side.

17. Coles Point Marina

Hague

John

CA $366 total

includes taxes & fees

Nov 17 - Nov 18

A modern kitchen with dark cabinets, a dishwasher, and a countertop with a sink.

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

Leonardtown

Christy C.

CA $790 total

includes taxes & fees

Nov 11 - Nov 12

A lakeside view from a deck with a wooden railing, a sandy area with a boat, and a dock extending into the water.

19. 2 bedroom waterfront property. Newly remodeled apartment with peaceful vibes.

Cambridge

CA $367 total

includes taxes & fees

Nov 11 - Nov 12

A grassy area with a wooden dock extending into a calm body of water, surrounded by trees and greenery.

20. Waterfront Getaway with Dock

Woolford

Mills Family A.

CA $358 total

includes taxes & fees

Nov 11 - Nov 12

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Top St. Leonard Hotel Reviews

Spark by Hilton California Lexington Park

California

10/10 Excellent

Aaron

A covered outdoor seating area with wicker furniture and large windows.

Hilton Garden Inn Solomons

Solomons

8/10 Good

Anonymous traveller

A reception area with a check-in counter, seating area, and a vending machine.

SureStay by Best Western Prince Frederick

Prince Frederick

10/10 Excellent

Yama

A modern hotel lobby with seating areas, a reception desk, and a staircase.

La Quinta Inn & Suites by Wyndham Lexington Park - Patuxent

California

10/10 Excellent

Harold

A hotel lobby with a dining area, seating, a fireplace, and a view of the outside through large windows.

Hampton Inn by Hilton Lexington Park

Lexington Park

8/10 Good

Enjoyed our stay (in the area for the weekend for business), but there were some significant problems: -sever lack of parking; both nights we had to park nearby since the lot was full and got a parking ticket first night (not hotel's problem with the ticket, but the small parking lot is in their control) -dog in the next room barked most of the weekend, front desk said all they could do was notify the owner (broken sleep both nights due to the barking at all hours) -reserved a king room, was...

Pamela

A wooden chair on a balcony overlooking a sunset over a body of water.

Island Inn & Suites, an Ascend Collection Hotel

Piney Point

8/10 Good

Luisa

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, cottages, cabins, villas... 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 months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A St. Leonard vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of St. Leonard vacation rentals we have selected for you start as low as CA $111 per night. Entering your travel dates in the search wizard 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.

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.

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St. Leonard Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for St. Leonard vacation rentals

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

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

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

4. Plum Point Cottage #14

5. Lakefront Cabin Near Solomons Island w/ Hot Tub

6. Plum Point Cottage #15

7. Plum Point Cottage #17

8. Soul Oasis - home on the Chesapeake Bay

9. Bright and airy waterfront getaway

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

11. Lakefront Cabin Near Solomons Island w/ Hot Tub

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

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

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

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

16. 4-BR Waterfront Turret Home

17. Coles Point Marina

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

19. 2 bedroom waterfront property. Newly remodeled apartment with peaceful vibes.

20. Waterfront Getaway with Dock

Find vacation rentals that suit your style

Top St. Leonard Hotel Reviews

Spark by Hilton California Lexington Park

10/10 Excellent

Find out more about St. Leonard

St. Leonard vacation rentals: An excellent choice for every season

How to find incredible deals on St. Leonard rentals

Frequently Asked Questions

Can I find a vacation rental in St. Leonard?

What's the top vacation rental that St. Leonard has to offer?

How many vacation rentals are there in St. Leonard?

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

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

Explore a world of travel with Expedia