St. Leonard Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out
  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals
  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings
  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for St. Leonard vacation rentals

10.0 out of 10, Exceptional, (31)
"Perfect place to spend quality time with our three adult children and their significant others. "
United States
Malarkey F.
$353 nightly
The price is $390
Jan 4 - Jan 5, 2026
Total with taxes and fees
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
10.0 out of 10, Exceptional, (17)
"We loved our stay! The property was just as advertised and had everything we needed. Quiet area and felt very safe. The owners provided excellent communication as well!"
United States
Jennifer B.
$292 nightly
The price is $322
Jan 11 - Jan 12, 2026
Total with taxes and fees
Walk to Beach! King Bed & Free Beach Passes
9.8 out of 10, Exceptional, (40)
"Great stay. Teresa was very helpful, the house is fun, and the location is great - nice place to visit."
United States
Samuel W.
$252 nightly
The price is $267
Jan 5 - Jan 6, 2026
Total with taxes and fees
Soul Oasis - home on the Chesapeake Bay
9.4 out of 10, Exceptional, (6)
"Great place to stay for a getaway "
United States
Adam W.
$156 nightly
The price is $172
Jan 3 - Jan 4, 2026
Total with taxes and fees
Cozy centrally located studio with WiFi and AC in peaceful Port Republic, MD
9.6 out of 10, Exceptional, (4)
"Great place in a wonderful area! So cozy & well situated! A perfect weekend getaway!"
United States
Jana S.
$260 nightly
The price is $276
Jan 1 - Jan 2, 2026
Total with taxes and fees
Charming 2-bedroom 1 bath cottage with AC, WiFi in peaceful North Beach, Md.
10.0 out of 10, Exceptional, (48)
"We love this place!"
United States
Joan K.
$293 nightly
The price is $311
Jan 8 - Jan 9, 2026
Total with taxes and fees
Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.

Vacation Home in Solomons

4-BR Waterfront Turret Home
2.0 star property
10.0 out of 10, Exceptional, (7)
"Beautiful house. Beautiful scenery. Everything was perfect. "
United States
Thomas S.
$680 nightly
The price is $751
Jan 1 - Jan 2, 2026
Total with taxes and fees
4-BR Waterfront Turret Home
10.0 out of 10, Exceptional, (50)
"Beautiful place! Loved all the activities, will return in the future! Our family and friends had a blast! Thank you so much!!"
United States
Karen L.
$352 nightly
The price is $373
Jan 4 - Jan 5, 2026
Total with taxes and fees
Beautiful Waterfront Retreat in Cambridge!

Cottage in Prince Frederick

Cottage Located on the Patuxent River!
10.0 out of 10, Exceptional, (42)
"This place was very lovely. Beautiful atmosphere and very spacious cottage. Didn’t get to see the owners but really enjoyed their property. Loved having the coffee maker, comfy bed and awesome tub! I will definitely be back. "
United States
RACHEL S.
$300 nightly
The price is $317
Jan 1 - Jan 2, 2026
Total with taxes and fees
Cottage Located on the Patuxent River!

Vacation Home in Chesapeake Beach

Family Beach House: Spacious Deck, Grill & Views
9.0 out of 10, Wonderful, (6)
"Everything was great. The owner was extremely helpful. Couldn't ask for anything better."
United States
Bryan P.
$421 nightly
The price is $443
Jan 29 - Jan 30, 2026
Total with taxes and fees
Family Beach House: Spacious Deck, Grill & Views
10.0 out of 10, Exceptional, (14)
"Second time staying at this lovely, serene home/property. It’s the perfect getaway if you’re looking to escape into some peace! Highly recommend "
United States
Jill C.
$498 nightly
The price is $528
Jan 2 - Jan 3, 2026
Total with taxes and fees
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
3.0 star property
$815 nightly
The price is $905
Jan 4 - Jan 5, 2026
Total with taxes and fees
Lakefront Log Cabin Retreat w/ Hot tub + Kayaks!
10.0 out of 10, Exceptional, (1)
"Beautiful newly renovated space with all new appliances, furniture and kitchenware. Comfortable beds, and super clean rooms. Large outside area with new Weber grill, fire pit, and three kayaks. Nice easy to access dock. "
United States
Kit C.
$514 nightly
The price is $568
Jan 1 - Jan 2, 2026
Total with taxes and fees
Charming Waterfront 3-bedroom house in Piney Point
9.0 out of 10, Wonderful, (8)
"The owner was very nice "
United States
karen
$271 nightly
The price is $299
Jan 1 - Jan 2, 2026
Total with taxes and fees
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
9.6 out of 10, Exceptional, (5)
"We had a short stay after a sporting event in DC, it was a little less than an hour away. Convenient location and a very clean house. Kitchen was well stocked. There was little communication with the owner, which was nice vs a long list of rules, but we would have liked to know any of their local specific favorite spots or more detailed check in/check out. Worked out nicely for our family. "
United States
Carrie K.
$367 nightly
The price is $389
Jan 4 - Jan 5, 2026
Total with taxes and fees
Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.
10.0 out of 10, Exceptional, (5)
"Everything was very clean and well put together. Loved the view!"
United States
Minji S.
$456 nightly
The price is $459
Jan 3 - Jan 4, 2026
Total with taxes and fees
Waterfront Escape | Family-Friendly | Remodeled Home | Epic Sunset Views | Decks

Vacation Home in Leonardtown

Potomac Vista Cottage
2.0 star property
$381 nightly
The price is $384
Jan 4 - Jan 5, 2026
Total with taxes and fees
Potomac Vista Cottage

Vacation Home in Woolford

Waterfront Getaway with Dock
10.0 out of 10, Exceptional, (51)
"Great place, will stay again"
United States
Matt S.
$263 nightly
The price is $279
Jan 6 - Jan 7, 2026
Total with taxes and fees
Waterfront Getaway with Dock
10.0 out of 10, Exceptional, (1)
"We loved our stay! Lovely home, beautiful view"
United States
Sarah R.
$868 nightly
The price is $874
Jan 6 - Jan 7, 2026
Total with taxes and fees
Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock
10.0 out of 10, Exceptional, (8)
"Everything was amazing. "
United States
Lorie S.
$385 nightly
The price is $408
Jan 14 - Jan 15, 2026
Total with taxes and fees
2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!
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.
Save an average of 15% on thousands of hotels when you're signed in

Top St. Leonard Hotel Reviews

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 $373 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.

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?

Beach Combing & Relaxation: This St. Leonard vacation home rental is located in a rural location and has a patio, a selection of games, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Our travelers also rate Discover tranquility near Calvert Cliffs as a favorite home for rent in St. Leonard.

How many vacation rentals are there in St. Leonard?

With 16 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.