St. Leonard Vacation Rentals from $248: Search Short-Term Rentals

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.

Check prices for these dates

In two weeks

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Our top choices for St. Leonard vacation rentals

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

Saint Leonard

Nancy P.

$234 nightly

Sep 23 - Sep 24

Total with taxes and fees

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

Benedict

ed r.

$241 nightly

Sep 21 - Sep 22

Total with taxes and fees

3. Soul Oasis - home on the Chesapeake Bay

Lusby

Dusty S.

$277 nightly

Sep 30 - Oct 1

Total with taxes and fees

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

Chesapeak beach

Bryan P.

$436 nightly

Sep 21 - Sep 22

Total with taxes and fees

5. Bright and airy waterfront getaway

Benedict

George

$335 nightly

Sep 21 - Sep 22

Total with taxes and fees

6. Plum Point Cottage #17

Huntingtown

$415 nightly

Sep 21 - Sep 22

Total with taxes and fees

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

North Beach

Johanna S.

$314 nightly

Sep 28 - Sep 29

Total with taxes and fees

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

North Beach

Penny N.

$419 nightly

Sep 27 - Sep 28

Total with taxes and fees

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Top St. Leonard Hotel Reviews

Rod 'N' Reel Resort

10/10 Excellent

"very clean"

Wylder Tilghman Island

8/10 Good

"Property is well maintained and clean. The rooms are small but adequate. Our only fault was the restaurant pricing. Dishes are at least 25 to 40 percent upvharged. For example, a bowl of gazpacho was priced at $18 . If crab eas added it would have been $15 more for a grand total of $33 for a bowl of soup. Outrageous. I’ve been to 5 star restaurants and never paid that much for a bowl of soup. The chicken entree was $30 and the chicken consisted of 2 small chicken finger type pieces. No full breast or thigh/leg. Drinks definitely upcheged. Drive a bit down the road and eat at Chesapeake seafood or drive into town. If you don’t feel comfortable driving at night, go in and have a late lunch or get takeout."

Historic 1825 Chesapeake Farm Stay

10/10 Excellent

"I booked a weekend stay here for my wife and I for our 30th anniversary. The house was amazing. There has been a lot of effort put into its decor which adds plenty of character to this historic hosue.Its very warm and welcoming. We were greeted by Holly upon our arrival she made us feel comfortable immediately. She prepares a continental breakfast every morning that sets the bar for how others should be.( everything was delicious)There are plenty of areas to hang out comfortably inside as well as outside the house. We did not take advantage of wonderful pool table while we were there,maybe on the next trip.The house is located in a quiet area and it was very peaceful,it was a welcome break from our hectic everyday life. This bed and breakfast is located conveniently to a lot of local attractions ex. Calvert Cliffs, Calvert Marine Museum, Solomons Island etc. I would highly recommend this place to anyone looking for a place to stay in this area. My biggest complaint is that we enjoyed it so much that we didn't want leave and return to normal everyday life after the relaxing weekend we spent there."

Spark by Hilton California Lexington Park

8/10 Good

"The room was very clean and quiet throughout the night, Breakfast staff was very friendly and accommodating. I wish there was more of a variety for breakfast. Fresh fruit and cooked eggs would have been nice. Overall good stay. I would recommend staying here."

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 $248 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.

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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?

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 Flag Ponds Nature Park 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 Northern 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.

St. Leonard Vacation Rentals

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

3. Soul Oasis - home on the Chesapeake Bay

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

5. Bright and airy waterfront getaway

6. Plum Point Cottage #17

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

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

9. 4-BR Waterfront Turret Home

10. Lakefront Cabin Near Solomons Island w/ Hot Tub

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

12. Lakefront Cabin Near Solomons Island w/ Hot Tub

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

14. Coles Point Marina

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

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

17. Cozy Virginia Potomac Riverfront Cottage

18. Waterfront Getaway with Dock

19. Sunset Breezes - quiet waterfront retreat

Find vacation rentals that suit your style

Top St. Leonard Hotel Reviews

Rod 'N' Reel Resort

Find out more about St. Leonard

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