Leonardtown Vacation Rentals

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Check prices for these dates

In two weeks
Dec 19 - Dec 21
In two months
Jan 30 - Feb 1
In three months
Feb 27 - Mar 1
In four months
Mar 27 - Mar 29

Vacation Rentals in Leonardtown

TV, fireplace, DVD player, books
Cheery, Peaceful Water Front Cabin on Winery Grounds

Cheery, Peaceful Water Front Cabin on Winery Grounds

Colonial Beach
9.8 out of 10, Exceptional, (56)
"Very quiet and great location."
United States
Cindy B.
$172 nightly
The price is $187
Dec 14 - Dec 15
Total with taxes and fees
Cheery, Peaceful Water Front Cabin on Winery Grounds
Terrace/patio
Tiny, Funky, and Full of Love - Welcome to the Love Shack

Tiny, Funky, and Full of Love - Welcome to the Love Shack

Piney Point
10.0 out of 10, Exceptional, (14)
"The place had everything we needed and the yard was great for the dogs. Would definitely stay here again."
United States
Dawn B.
Tiny, Funky, and Full of Love - Welcome to the Love Shack
Exterior
Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp

Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp

Drayden
9.8 out of 10, Exceptional, (78)
"Host was gracious. house is well prepared and clean. "
United States
Mark A.
Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp
Sun loungers, beach towels
Soul Oasis - home on the Chesapeake Bay

Soul Oasis - home on the Chesapeake Bay

Lusby
9.8 out of 10, Exceptional, (38)
"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 8 - Dec 9
Total with taxes and fees
Soul Oasis - home on the Chesapeake Bay
Pool
Inviting and Serene Home on Monroe Bay Creek

Inviting and Serene Home on Monroe Bay Creek

Colonial Beach
10.0 out of 10, Exceptional, (83)
"This was my 3 stay at Shannon's beautiful home. My family, friends and I equally adore the home, the serene surroundings and Shannon's hospitality. I completely recommend this property 10 out of 10!"
United States
Teshara C.
Inviting and Serene Home on Monroe Bay Creek
Property grounds
Pet Friendly Delightful Waterfront Cottage on Hoopers Island, MD.

Pet Friendly Delightful Waterfront Cottage on Hoopers Island, MD.

Fishing Creek
10.0 out of 10, Exceptional, (51)
"Nice "
United States
Henry
Pet Friendly Delightful Waterfront Cottage on Hoopers Island, MD.
Microwave, oven, stovetop, dishwasher
Spacious 6-Bedroom Solomons Island Retreat • Walk to Waterfront & Shops

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

Solomons
9.6 out of 10, Exceptional, (8)
"Stayed for business, completed our project and enjoyed some local eating spots. "
United States
Justin J.
Spacious 6-Bedroom Solomons Island Retreat • Walk to Waterfront & Shops
Dining
Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay

Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay

Port Republic
10.0 out of 10, Exceptional, (181)
"We thoroughly enjoyed our stay in this kitschy, cool, rustic cabin with a million-dollar view. Communing with the ospreys, hummingbirds and the bald eagle who perched numerous times on a nearby tree was an added bonus. And, the owner may be the most friendly/helpful we’ve ever rented from. We hope to be back some day. Thanks!"
United States
Brennan H.
Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay
Fridge, microwave, oven, stovetop
Coastal Charm and Convenience: Luxurious 5-Bedroom Just Steps From Downtown

Coastal Charm and Convenience: Luxurious 5-Bedroom Just Steps From Downtown

Colonial Beach
9.8 out of 10, Exceptional, (19)
"So convenient to the beach and downtown Colonial Beach restaurants and shopping. We will definitely be back! "
United States
Marisa Z.
Coastal Charm and Convenience: Luxurious 5-Bedroom Just Steps From Downtown
Marina
Colonial Beach Cottage, 7 minutes walk to beach!

Colonial Beach Cottage, 7 minutes walk to beach!

Colonial Beach
9.2 out of 10, Wonderful, (35)
"Easy check in, over all nice place with a very convenient location. Property owner VERY responsive and excellent. We had a great 3 night 4 day stay."
United States
Kye H.
Colonial Beach Cottage, 7 minutes walk to beach!
Smart TV, fireplace
Bay view from Calvert Cliffs, Solomons Island & State Park nearby

Bay view from Calvert Cliffs, Solomons Island & State Park nearby

Lusby
10.0 out of 10, Exceptional, (63)
"Such a beautiful place to stay. Had absolutely everything you could need. Comfy beds and tons of space. Definitely recommend staying here!"
United States
Whitney H.
Bay view from Calvert Cliffs, Solomons Island & State Park nearby
Fridge, microwave, oven, stovetop
Luxurious 3 Bedroom Riverfront Condo with Private Deck

Luxurious 3 Bedroom Riverfront Condo with Private Deck

2.0 star property
Colonial Beach
10.0 out of 10, Exceptional, (13)
"Beautiful place and very clean will be going back next uear"
United States
Connie S.
Luxurious 3 Bedroom Riverfront Condo with Private Deck
Beach
Sunnyside Up - Small Dog Friendly Waterfront Cottage

Sunnyside Up - Small Dog Friendly Waterfront Cottage

Colonial Beach
10.0 out of 10, Exceptional, (23)
"Very comfortabe with excellent location."
United States
Ray W.
Sunnyside Up - Small Dog Friendly Waterfront Cottage
Dining
Cozy Virginia Potomac Riverfront Cottage

Cozy Virginia Potomac Riverfront Cottage

Hague
9.6 out of 10, Exceptional, (46)
"Wonderful views, clean home and quaint ! We highly recommend!"
United States
Tim R.
Cozy Virginia Potomac Riverfront Cottage
Fridge, microwave, oven, stovetop
Call to reserve last minute stay! Hideaway in Hays Beach: 1 Minute Walk to Sand

Call to reserve last minute stay! Hideaway in Hays Beach: 1 Minute Walk to Sand

Point Lookout
10.0 out of 10, Exceptional, (125)
"Really enjoyed our time here. The outdoor space in the back was great with the swing and the fire pits. Our kids loved walking to the beach everyday and catching crabs. "
United States
David Z.
Call to reserve last minute stay! Hideaway in Hays Beach: 1 Minute Walk to Sand
Terrace/patio
Relax & Renew in a WATERFRONT Cottage , private pier, kayaks, fishing, wineries.

Relax & Renew in a WATERFRONT Cottage , private pier, kayaks, fishing, wineries.

Lottsburg
10.0 out of 10, Exceptional, (62)
"We had a wonderful stay for Labor Day weekend. So much is provided by the owners, paddle boards, kayak, water mats, everything you need to enjoy the water. The house is beautifully decorated, clean and well stocked. Don't miss the sunrises. Hope to be back."
United States
Robin M.
Relax & Renew in a WATERFRONT Cottage , private pier, kayaks, fishing, wineries.
Smart TV, fireplace, books, offices
Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier

Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier

Port Republic
10.0 out of 10, Exceptional, (124)
"Well, what a great time we had at this house the house is exactly as advertised, tidy, clean, comfortable, everything close. The view was beautiful, our vacation was amazing. Alicia was very responsive to any question that we had. We definitely would rent again!"
United States
Misael A A.
Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier
Interior
Game Themed Fun! Boats+Beach+King Bd+EV Chrgr

Game Themed Fun! Boats+Beach+King Bd+EV Chrgr

Montross
10.0 out of 10, Exceptional, (30)
"Comfy, relaxing, beautiful, relaxing vacation home. We went to unwind and the facilities and owners were a delight. Kitchen was super well stocked with everything needed to handle meals for 11 people. Popcorn was a smash. The front door unlocked with our code and we were all ready to expand and kick off 9 days together."
United States
Al F.
$424 nightly
The price is $461
Dec 7 - Dec 8
Total with taxes and fees
Game Themed Fun! Boats+Beach+King Bd+EV Chrgr
Smart TV, printers
Secluded Riverfront Retreat on 100+ Acre Farm in Mechanicsville, WiFi, AC, &More

Secluded Riverfront Retreat on 100+ Acre Farm in Mechanicsville, WiFi, AC, &More

Mechanicsville
10.0 out of 10, Exceptional, (7)
"My first thought was "gorgeous", when i walked through the door. This was just the weekend I needed. The screened in porch was relaxing. Be ready to take pictures of the sunrise! "
United States
Lisa R.
Secluded Riverfront Retreat on 100+ Acre Farm in Mechanicsville, WiFi, AC, &More
Property grounds
Waterfront Sunsets, Fishing, Boating, and Crabs! Paxs River, Budds Creek MIR.

Waterfront Sunsets, Fishing, Boating, and Crabs! Paxs River, Budds Creek MIR.

Maddox
10.0 out of 10, Exceptional, (15)
"Chris and his wife Lynda were absolutely amazing. They included us in their activities and showed us around a bit. We now consider them family! Super prompt with questions, activities, and information about the surrounding area! Loved every minute of our time at the cottage. "
United States
Kim K.
Waterfront Sunsets, Fishing, Boating, and Crabs! Paxs River, Budds Creek MIR.
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 Leonardtown Hotel Reviews

River Edge Inn

River Edge Inn

10/10 Excellent
"My hotel door opened up to (I’m not good with distance so I have no idea what I’m saying, but) essentially 100 steps from the beach🏖️. AMAZING, so cool! (Note this is a river beach, not an ocean—but still very beautiful & blissful.) definitely a diamond in a rough spot. I parked my car right in front of my hotel door. Grabbed pizza to go just up the block (and there’s a nice grocery store just up the block for whatever other snacks you want!) there’s a mini fridge in the hotel. **Apologies for my sorta poor quality photos! I forgot to take photos. I only took an AMAZING video of my view walking to the beach from my front door in the morning at sunrise. This review seems to not let me post a video— so for this review, my photos are screenshots I captured from my video.)☺️🌅 Oh & this place is pet friendly. Two other hotel families had a dog. They had smaller dogs. I assume policy extends to bigger dogs."
Kirsten 1-night trip
Posted 2 days ago
River Edge Inn

Find out more about Leonardtown

Everything you need to know about Leonardtown 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 Leonardtown 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 Leonardtown vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Leonardtown vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Leonardtown. 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 Leonardtown 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 $187 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 Leonardtown rentals

At Expedia, we put the best Leonardtown 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 Leonardtown 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 Leonardtown 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 Leonardtown. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Are there vacation rentals in Leonardtown?

Yes, there are vacation rentals in Leonardtown near Saint Mary's Fairground, or you can choose a more secluded option if you're looking for extra privacy while you relax. Leonardtown is known for its seafood restaurants and festivals. Make sure you have time to check out the sporting events while you're in the area.

What are some of the best vacation rentals that Leonardtown has to offer?

Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp: This vacation home rental near Leonardtown is located on the beach and has a balcony, a garden, 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. You and your friends and family can relax into your vacation with amenities like a selection of games.

How many vacation rentals will I find in Leonardtown?

With 11 Expedia vacation rentals, you're sure to find just the right place for your Leonardtown stay.

What’s there to see and do in Leonardtown?

St. Mary's River State Park and Leonardtown Park are a couple of lovely local spots to get outside and enjoy nature. While here, Leonardtown Town Hall and Breton Bay Golf Course are other places worth a visit.

What’s a vacation rental in Leonardtown like?

Vacation rentals are privately owned properties you can stay in for a few weeks or just a few days in Leonardtown. Vacation rentals offer extras such as WiFi and washers and dryers so you'll be comfy for your stay. If you're concerned about a sanitized environment, a vacation rental can offer a sense of privacy away from public hotel elevators and busy front desks while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a great option for a family trip.