St. Leonard Vacation Rentals

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Vacation Rentals in St. Leonard

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
Nov 17 - Nov 18
Total with taxes and fees
Soul Oasis - home on the Chesapeake Bay

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. Quiet comfortable neighborhood, plenty to do around if you’re outdoorsy. The location was comfortable & well stocked with anything you’d need. Would return. "
United States
Caleb 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

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

Owings
10.0 out of 10, Exceptional, (48)
"Lovely property."
United States
Melissa W.
$246 nightly
The price is $261
Nov 20 - Nov 21
Total with taxes and fees
Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.

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.
$312 nightly
The price is $345
Nov 17 - Nov 18
Total with taxes and fees
Walk to Beach! King Bed & Free Beach Passes

Peaceful Waterfront Apartment in the Heart of Solomons Island

Solomons
9.0 out of 10, Wonderful, (14)
"Very clean, awesome location and amazing hosts!! "
United States
Jeff R.
$262 nightly
The price is $278
Nov 17 - Nov 18
Total with taxes and fees
Peaceful Waterfront Apartment in the Heart of Solomons Island

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 21 - Nov 22
Total with taxes and fees
Charming 2-bedroom 1 bath cottage with AC, WiFi in peaceful North Beach, Md.

4-BR Waterfront Turret Home

2.0 star property
Solomons
10.0 out of 10, Exceptional, (7)
"A truly incredible property. Home is beyond beautiful, interesting design, terrific location where the river meets the bay. Saw dolphins jumping. Easy walk to downtown and restaurants. Turret style home is fascinating. Host incredibly accessible. Rent with confidence."
United States
Laura
$668 nightly
The price is $738
Dec 1 - Dec 2
Total with taxes and fees
4-BR Waterfront Turret Home

Modern Waterfront Home with Kayak, Firepit, Gameroom, Pool+Beaches, Dog & EV OK

Montross
10.0 out of 10, Exceptional, (4)
"They thought of everything. I would definitely come back for another stay."
United States
Donna D.
$376 nightly
The price is $410
Nov 17 - Nov 18
Total with taxes and fees
Modern Waterfront Home with Kayak, Firepit, Gameroom, Pool+Beaches, Dog & EV OK

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.
$405 nightly
The price is $447
Nov 19 - Nov 20
Total with taxes and fees
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

Family Beach House: Spacious Deck, Grill & Views

Chesapeake Beach
9.0 out of 10, Wonderful, (6)
"This house could not have a better location. There’s a gorgeous beach right across the street. My family and I spent many hours walking the beach looking for beach glass and shark teeth, which were surprisingly plentiful. There was even a nice dock to fish on. The house is very well kept. The upstairs table on the patio was a favorite of mine. The owner was in constant contact. We had a blast."
United States
Jeff B.
$379 nightly
The price is $397
Dec 15 - Dec 16
Total with taxes and fees
Family Beach House: Spacious Deck, Grill & Views

Beautiful Waterfront Retreat in Cambridge!

Cambridge
10.0 out of 10, Exceptional, (49)
"Wonderful stay. The Crab Shack and dock were the highlights. We spent most of our time there. It was awesome. Highly recommend. "
United States
Christopher D.
$357 nightly
The price is $378
Nov 30 - Dec 1
Total with taxes and fees
Beautiful Waterfront Retreat in Cambridge!

Spacious 6-Bedroom Solomons Island Retreat • Walk to Waterfront & Shops

Solomons
9.6 out of 10, Exceptional, (7)
"The house was beautiful and well stocked with the necessities and even extras we didn’t expect. The service from the owner was great and always quick to respond to our questions. We are definitely looking forward to staying at this or another property next year! "
United States
Shewana S.
$512 nightly
The price is $542
Nov 17 - Nov 18
Total with taxes and fees
Spacious 6-Bedroom Solomons Island Retreat • Walk to Waterfront & Shops

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

Lexington Park
10.0 out of 10, Exceptional, (5)
"I recently stayed at this property and had a wonderful experience. Trey was a terrific host. The location is fantastic, offering easy access to St. Mary’s College. The water view and sunsets were amazing. The cleanliness of the property was impeccable and the host did a great job of stocking the house with everything we needed. The full kitchen with labeled drawers made cooking easy. The house was roomy and the beds were extremely comfortable. It is a great set up for families. Overall, I highly...
United States
Lisa M.
$359 nightly
The price is $361
Nov 17 - Nov 18
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
9.4 out of 10, Exceptional, (3)
"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.
$327 nightly
The price is $347
Nov 24 - Nov 25
Total with taxes and fees
Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.

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

Benedict
9.0 out of 10, Wonderful, (6)
"Sophia the host is super attentive and responsive"
United States
Mayela
$271 nightly
The price is $299
Nov 17 - Nov 18
Total with taxes and fees
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.

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.
$519 nightly
The price is $573
Nov 17 - Nov 18
Total with taxes and fees
Charming Waterfront 3-bedroom house in Piney Point

Waterfront Getaway with Dock

Woolford
10.0 out of 10, Exceptional, (51)
"Great place, will stay again"
United States
Matt S.
$255 nightly
The price is $270
Nov 17 - Nov 18
Total with taxes and fees
Waterfront Getaway with Dock

Tranquil Modern Farmhouse

Waldorf
9.4 out of 10, Exceptional, (6)
"This property was super gorgeous and spacious so we were able to relax. Guests had more than enough space and didn’t feel like they were on top of each other sleeping wise! We were able to just have dinner and feel safe! The owner answered any questions we had within 15 minutes, which was super helpful! "
United States
khaddija j.
$479 nightly
The price is $529
Nov 17 - Nov 18
Total with taxes and fees
Tranquil Modern Farmhouse

Lakefront Log Cabin Retreat 3br-2ba Hot Tub+kayaks

3.0 star property
Lusby
$655 nightly
The price is $727
Nov 18 - Nov 19
Total with taxes and fees
Lakefront Log Cabin Retreat 3br-2ba Hot Tub+kayaks

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

Cambridge
10.0 out of 10, Exceptional, (14)
"very serene, peaceful home on the bay! Amazing getaway! "
United States
Jill C.
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
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.