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Leonardtown Vacation Rentals

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Oct 22 - Oct 23
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Oct 23 - Oct 24
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Oct 24 - Oct 26
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Oct 31 - Nov 2

Vacation Rentals in Leonardtown

Terrace/patio
Tiny, Funky, and Full of Love - Welcome to the Love Shack
Tiny, Funky, and Full of Love - Welcome to the Love Shack
10.0 out of 10, Exceptional, (11)
"Such a great accommodation!!! We were here for a swim meet in town and Katie was the greatest host. We had all the comforts and amenities needed. We will def be staying again. "
United States
Joleen H.
Tiny, Funky, and Full of Love - Welcome to the Love Shack
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
10.0 out of 10, Exceptional, (180)
"Cottage was just as pictured. Lots of character and charm. Host, Brett was easy to work with and very helpful!"
United States
Michelle R.
Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay
Terrace/patio
Potomac Rvr Woodland Cottage, Polite Pets welcomed, Central Air, Stunning Sunset
Potomac Rvr Woodland Cottage, Polite Pets welcomed, Central Air, Stunning Sunset
9.8 out of 10, Exceptional, (56)
"We had a wonderful experience and stay at this cute little cottage. Hosts were amazing as well. Cottage has everything you need. Cute decor, plenty of cookware, towels, linens, TV with streaming and comfortable couch. Communication with host was outstanding and easy check-in and check-out. Will definitely stay here again and strongly recommend to others as a place to stay in the area."
United States
Mary S.
Potomac Rvr Woodland Cottage, Polite Pets welcomed, Central Air, Stunning Sunset
TV, fireplace, DVD player, books
Cheery, Peaceful Water Front Cabin on Winery Grounds
Cheery, Peaceful Water Front Cabin on Winery Grounds
9.8 out of 10, Exceptional, (53)
"Great spot for a family of 4. Very quiet and clean."
United States
Zach H.
$170 nightly
The price is $184
Oct 27 - Oct 28
Total with taxes and fees
Cheery, Peaceful Water Front Cabin on Winery Grounds
Property grounds
Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing
Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing
9.8 out of 10, Exceptional, (151)
"The place was great, the host was great,"
United States
Travis
Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing
Interior
Waterfront with spectacular view, close to restaurants and bars
Waterfront with spectacular view, close to restaurants and bars
9.8 out of 10, Exceptional, (55)
"We enjoyed our stay here! The place was incredibly clean and the view was perfect! "
United States
Rachel S.
Waterfront with spectacular view, close to restaurants and bars
Interior
Waterfront Solomons Apartment
Waterfront Solomons Apartment
9.2 out of 10, Wonderful, (13)
"Very clean, awesome location and amazing hosts!! "
United States
Jeff R.
$254 nightly
The price is $269
Oct 24 - Oct 25
Total with taxes and fees
Waterfront Solomons Apartment
Interior
Waterfront Wildlife Retreat on the Patuxent River
Waterfront Wildlife Retreat on the Patuxent River
10.0 out of 10, Exceptional, (172)
"We went here just for a little weekend getaway for my boyfriend, his brother, his brother’s girlfriend and their kids. We had the absolute best time, such a nice getaway even if it was only for 3 days. The view of the bay from the house is gorgeous and everything was perfect. I will be recommending this stay to anyone I can! "
United States
Nicole V.
Waterfront Wildlife Retreat on the Patuxent River
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
9.8 out of 10, Exceptional, (76)
"The property is just as listed! Thoroughly enjoyed the house, the grounds, and the beach! Rick was accommodating and responsive. What a great place!"
United States
David and Ilana X.
Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp
Beach
Belle of the Chesapeake Bay
Belle of the Chesapeake Bay
9.2 out of 10, Wonderful, (16)
"Excellent communication from the owner, Julie and the property manager. Our family (newborn to adults) stayed at this property while in town for a wedding at Rousby Hall. We were a quick and easy 15 minute drive away from the venue. The house was very clean and nicely set up to accommodate our group. We only wish we had more time to spend at the house than we did. The pictures are exactly what you see when you check in - no unhappy surprises. Thank you for hosting us and being so flexible...
United States
eileen b.
Belle of the Chesapeake Bay
Fridge, microwave, oven, stovetop
A Hideaway in Hays Beach: Chesapeake Bay, 5G WiFi, 60 Second Walk to Beach
A Hideaway in Hays Beach: Chesapeake Bay, 5G WiFi, 60 Second Walk to Beach
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.
A Hideaway in Hays Beach: Chesapeake Bay, 5G WiFi, 60 Second Walk to Beach
On the beach
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
9.6 out of 10, Exceptional, (5)
"Just the perfect place I needed for a personal retreat. It is quiet, peaceful and serene. I would definitely visit again. "
United States
Berenice N.
$271 nightly
The price is $299
Oct 24 - Oct 25
Total with taxes and fees
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Terrace/patio
El Camino
El Camino
10.0 out of 10, Exceptional, (49)
"Great location, the dock is perfect for sunsets, nice balance of waterfront but also cabin vibes"
United States
Alan B.
El Camino
Dining
3-bedroom house in charming Colonial Beach with AC, WiFi
3-bedroom house in charming Colonial Beach with AC, WiFi
10.0 out of 10, Exceptional, (7)
"Much more to offer that it seems. Highly recommended "
United States
Chris T.
3-bedroom house in charming Colonial Beach with AC, WiFi
Property grounds
Waterfront Cottage in Beautiful Hoopers Island
Waterfront Cottage in Beautiful Hoopers Island
10.0 out of 10, Exceptional, (80)
"Beautiful location, so peaceful and quiet, we loved our stay! "
United States
Janna C.
Waterfront Cottage in Beautiful Hoopers Island
Dining
Beachfront Hideaway - Pet Friendly, Hot Tub, EV
Beachfront Hideaway - Pet Friendly, Hot Tub, EV
9.8 out of 10, Exceptional, (11)
"From the time we arrived, we were enjoying the beautiful view. The host really made our stay wonderful as the home is set up with everything you need and then some extras. We really enjoyed the kayaks and paddle board during the day and brought along some floats for a little relaxation in the water. After dinner, we enjoyed the hot tub and beautiful sunset. We all left there well rested and wanting to come back soon. It was the perfect get away to kick off summer."
United States
LeAnn C.
Beachfront Hideaway - Pet Friendly, Hot Tub, EV
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
9.8 out of 10, Exceptional, (19)
"Very clean, great location, and comfortable beds, we had a great time. Walking distance to bars, restaurants, and coffee shops. Very convenient, and the owner was easy to work with. "
United States
Jim P.
Coastal Charm and Convenience: Luxurious 5-Bedroom Just Steps From Downtown
Terrace/patio
Waterfront Escape | Family-Friendly | Remodeled Home | Epic Sunset Views | Decks
Waterfront Escape | Family-Friendly | Remodeled Home | Epic Sunset Views | Decks
10.0 out of 10, Exceptional, (4)
"Everything was very clean and well put together. Loved the view!"
United States
Minji S.
$370 nightly
The price is $373
Oct 29 - Oct 30
Total with taxes and fees
Waterfront Escape | Family-Friendly | Remodeled Home | Epic Sunset Views | Decks
Smart TV, fireplace
Bay view from Calvert Cliffs, Solomons Island & State Park nearby
Bay view from Calvert Cliffs, Solomons Island & State Park nearby
10.0 out of 10, Exceptional, (59)
"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
Dining
Cozy Virginia Potomac Riverfront Cottage
Cozy Virginia Potomac Riverfront Cottage
9.6 out of 10, Exceptional, (45)
"We thoroughly enjoyed our stay. Thank you! "
United States
Cerkez C.
Cozy Virginia Potomac Riverfront Cottage
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
"Very friendly staff! This location is so convenient to all you want to see & do in Colonial Beach. Clean room & linens. Room could use a touch up of paint but that’s about it. "
Susan 2-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 $184 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?

Waterfront with spectacular view, close to restaurants and bars: This vacation home rental near Leonardtown is located on a river and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. You and your friends and family can relax into your vacation with amenities like a selection of books.

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, Port of Leonardtown Winery and Leonardtown Town Hall 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.