St. Leonard Vacation Rentals

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Vacation Rentals in St. Leonard

Walk to Beach! King Bed & Free Beach Passes

North Beach
10.0 out of 10, Exceptional, (16)
"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.
$297 nightly
The price is $328
Dec 1 - Dec 2
Total with taxes and fees
Walk to Beach! King Bed & Free Beach Passes

Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.

Owings
10.0 out of 10, Exceptional, (48)
"We love this place!"
United States
Joan K.
$235 nightly
The price is $249
Nov 30 - Dec 1
Total with taxes and fees
Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.

Soul Oasis - home on the Chesapeake Bay

Lusby
9.8 out of 10, Exceptional, (37)
"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
Dec 1 - Dec 2
Total with taxes and fees
Soul Oasis - home on the Chesapeake Bay

Charming 2-bedroom 1 bath cottage with AC, WiFi in peaceful North Beach, Md.

2.0 star property
North Beach
10.0 out of 10, Exceptional, (1)
"Great location! Everything was on hand and it was an easy sweet little cottage to be in.It was clean and very functional with the added bonus of being so close to all the activity in North Beach.Heather was responsive and obviously cares about her guests and their stay.Highly recommend! "
United States
Georgina P.
$261 nightly
The price is $277
Nov 30 - Dec 1
Total with taxes and fees
Charming 2-bedroom 1 bath cottage with AC, WiFi in peaceful North Beach, Md.

Cozy centrally located studio with WiFi and AC in peaceful Port Republic, MD

Port Republic
9.4 out of 10, Exceptional, (6)
"Great place to stay"
United States
Sherry R.
$156 nightly
The price is $172
Dec 5 - Dec 6
Total with taxes and fees
Cozy centrally located studio with WiFi and AC in peaceful Port Republic, MD

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

Benedict
9.2 out of 10, Wonderful, (7)
"The owner was very nice "
United States
karen
$271 nightly
The price is $299
Nov 28 - Nov 29
Total with taxes and fees
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.

Beautiful Waterfront Retreat in Cambridge!

Cambridge
10.0 out of 10, Exceptional, (49)
"Just what we were looking for. Appreciated the little touches such as already baited crab traps and the complimentary smores kit. "
United States
Dan K.
$357 nightly
The price is $378
Nov 30 - Dec 1
Total with taxes and fees
Beautiful Waterfront Retreat in Cambridge!

Lakefront Log Cabin Retreat w/ Hot tub + Kayaks!

3.0 star property
Lusby
$693 nightly
The price is $770
Nov 30 - Dec 1
Total with taxes and fees
Lakefront Log Cabin Retreat w/ Hot tub + Kayaks!

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

North Beach
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.
$419 nightly
The price is $462
Dec 1 - Dec 2
Total with taxes and fees
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

Cottage Located on the Patuxent River!

Prince Frederick
10.0 out of 10, Exceptional, (42)
"The accommodations were superb and being on the water was amazing!"
United States
Daniel P.
$300 nightly
The price is $317
Nov 28 - Nov 29
Total with taxes and fees
Cottage Located on the Patuxent River!

Waterfront Escape | Family-Friendly | Remodeled Home | Epic Sunset Views | Decks

Lexington Park
10.0 out of 10, Exceptional, (5)
"This was our second time staying at this beautiful home, and it was just as wonderful as we remembered. The house is impeccably maintained, tastefully decorated, and incredibly comfortable. The beds are cozy, and every detail has been thoughtfully considered—from the clear labels throughout the home to the fully stocked kitchen and amenities. It truly feels like a home away from home. We had a fantastic stay and are already looking forward to our next visit!"
United States
Lisa M.
$362 nightly
The price is $365
Nov 30 - Dec 1
Total with taxes and fees
Waterfront Escape | Family-Friendly | Remodeled Home | Epic Sunset Views | Decks

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

Prince Frederick
9.6 out of 10, Exceptional, (4)
"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.
$344 nightly
The price is $365
Dec 1 - Dec 2
Total with taxes and fees
Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.

Waterfront Getaway with Dock

Woolford
10.0 out of 10, Exceptional, (51)
"Great place, will stay again"
United States
Matt S.
$254 nightly
The price is $269
Dec 1 - Dec 2
Total with taxes and fees
Waterfront Getaway with Dock

Peaceful Waterfront Apartment in the Heart of Solomons Island

Solomons
9.0 out of 10, Wonderful, (14)
"Nice little place to stay"
United States
Eric S.
Peaceful Waterfront Apartment in the Heart of Solomons Island

2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!

Prince Frederick
10.0 out of 10, Exceptional, (8)
"Clean and easy "
United States
Robert R.
$332 nightly
The price is $352
Nov 30 - Dec 1
Total with taxes and fees
2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!

Peaceful tiny home Saltara where you can realx and unwind

2.0 star property
Lexington Park
$164 nightly
The price is $181
Nov 28 - Nov 29
Total with taxes and fees
Peaceful tiny home Saltara where you can realx and unwind

4-BR Waterfront Turret Home

2.0 star property
Solomons
10.0 out of 10, Exceptional, (7)
"Absolutely wonderful home with the best view of the water from nearly every window. It was clean and it had many comfortable bedrooms. Highly recommend this property!!"
United States
Rudy L.
$613 nightly
The price is $677
Dec 14 - Dec 15
Total with taxes and fees
4-BR Waterfront Turret Home

Sunset Breezes - quiet waterfront retreat

Dorchester County
10.0 out of 10, Exceptional, (41)
"Good time with my friends "
United Kingdom
Oleg L.
$263 nightly
The price is $290
Dec 23 - Dec 24
Total with taxes and fees
Sunset Breezes - quiet waterfront retreat

Waterfront home on Mill Creek-5BR-Hot tub & Kayaks

Lusby
10.0 out of 10, Exceptional, (1)
"We loved our stay! Lovely home, beautiful view"
United States
Sarah R.
$749 nightly
The price is $754
Dec 11 - Dec 12
Total with taxes and fees
Waterfront home on Mill Creek-5BR-Hot tub & Kayaks

Charming Waterfront 3-bedroom house in Piney Point

Piney Point
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.
$522 nightly
The price is $576
Nov 30 - Dec 1
Total with taxes and fees
Charming Waterfront 3-bedroom house in Piney Point
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

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 $267 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?

Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub: This vacation home rental near St. Leonard is located on the waterfront and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a balcony, a garden, and a hot tub so you can immerse yourself in your vacation.

How many vacation rentals are there in St. Leonard?

With 15 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 Jefferson Patterson Park and Museum 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.