St. Leonard Vacation Rentals from $261: Search Short-Term Rentals

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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.

$246 nightly

Sep 16 - Sep 17

Total with taxes and fees

2. Soul Oasis - home on the Chesapeake Bay

Lusby

Dusty S.

$286 nightly

Sep 9 - Sep 10

Total with taxes and fees

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

Benedict

karen

$234 nightly

Sep 8 - Sep 9

Total with taxes and fees

4. Bright and airy waterfront getaway

Benedict

William N.

$349 nightly

Sep 8 - Sep 9

Total with taxes and fees

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

Chesapeak beach

Bryan P.

$438 nightly

Sep 7 - Sep 8

Total with taxes and fees

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

North Beach

Johanna S.

$300 nightly

Sep 7 - Sep 8

Total with taxes and fees

7. 3-bedroom house in serene Lusby with refreshing AC, heat, outdoor fireplace

Lusby

$401 nightly

Sep 16 - Sep 17

Total with taxes and fees

8. Plum Point Cottage #17

Huntingtown

$415 nightly

Sep 7 - Sep 8

Total with taxes and fees

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Top St. Leonard Hotel Reviews

Island Inn & Suites, an Ascend Collection Hotel

8/10 Good

"My girls and I stayed here for a night while exploring the bay area. This hotel is remote, but very quiet and right on the water. Hotel room was clean and spacious and each room had a balcony overlooking the water on each side. It was fun to watch people crab and fish off the pier. Yes, breakfast was minimal, but staff very friendly and I felt safe. Would stay again if in the area."

Quality Inn Solomons - Beacon Marina

8/10 Good

"Everything was good, standard hotel/motel stuff: little coffee pot, mini-fridge, microwave, tv,a/c - everything worked as expected, furniture, carpeting, lights, bathroom all looked newish and everything was very clean. Desk folk were pleasant, didn’t have much interaction. The big plus is the location, right by a huge marina (if you like looking at boats) and the Calvert Marine Museum- combines natural history and the commercial history of the area, has the Drum Point lighthouse (you can tour) and a boat tour of Patuxent Harbor, plus fossils, river otters, fish. Calvert Cliffs / Flag Pond parks are a 10 minute drive if you want to dig for fossils yourself. So: comfortable place, very reasonably priced, close to all sorts of stuff; definitely worth it."

Wylder Tilghman Island

8/10 Good

"We are experienced travelers so expect certain information and common amenities at check-in or in the room. The following were NOT provided and/or were issues for us ... 1. Guest's WIFI Password was not provided at Reception or on a card in the room. 2. Two remotes were required to operate the TV with no instructions for how to use them. 3. There were no Ice Machines for Guests' use. 4. The Bathtub was quite old and slippery but no bath mat was provided. 5. The bath/shower mixing valve was very old, corroded and hard to turn ON/OFF. 6. The filter in the air conditioner was very dirty. 7. No hairdryer was provided in the room. 8. Before our arrival, the room was sprayed with a strong perfume that took the better part of a day to dissipate. 9. No telephone in the room to call the front desk or restaurant. 10. There aren't enough Chez Lounges around the pool. On the other hand, the following were plusses ... 1. The property and amenities offered are excellent. 2. The views of the Chesapeake are beautiful. 3. The grounds are well maintained with lots of varied seating options. 4. The help, wait staff and others were friendly, well-trained and helpful. 5. The food in the restaurant and drinks served from the bar were of good quality and not overpriced. I'm pleased to speak with the Manager about any of the foregoing if he/she wishes. F. J. Hammerle 510-333-9194"

Historic 1825 Chesapeake Farm Stay

10/10 Excellent

"This is a must see for yourself!! The owners have thought of every detail from the over the top welcome amenities to extras like offering beach chairs and towels to go explore the local beach! Breakfast was absolutely delicious! She even prepared a to go breakfast when she found out we had to leave out early one morning! We enjoyed home grown fruits and veggies from her garden daily! If you want to step back in time, but still have the comforts of modern day you have to got to visit this place! We will be back!!"

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.

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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?

Charming Waterfront Farmhouse 10 minutes from Blackwater NWR - Pet Friendly: This vacation home rental near St. Leonard is located on a river and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. You and your friends and family can relax into your vacation with amenities like a selection of games.

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 Northern Chesapeake Bay and Patuxent River.

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. Soul Oasis - home on the Chesapeake Bay

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

4. Bright and airy waterfront getaway

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

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

7. 3-bedroom house in serene Lusby with refreshing AC, heat, outdoor fireplace

8. Plum Point Cottage #17

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

10. 4-BR Waterfront Turret Home

11. Lakefront Cabin Near Solomons Island w/ Hot Tub

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

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

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

15. Lakefront Cabin Near Solomons Island w/ Hot Tub

16. Sunset Breezes - quiet waterfront retreat

17. Cozy Virginia Potomac Riverfront Cottage

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

19. Coles Point Marina

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

Find vacation rentals that suit your style

Top St. Leonard Hotel Reviews

Island Inn & Suites, an Ascend Collection Hotel

Find out more about St. Leonard

Explore a world of travel with Expedia

Frequently asked questions

Expedia's Latest Trends

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