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Leonardtown Holiday Rentals

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Holiday Rentals in Leonardtown

Blue Heron Cottage is cozy & convenient. Renovated March 2023!
10.0 out of 10, Exceptional, (32)
"This is a great cottage . Close to everything, but in a quaint quiet neighborhood. You won’t be disappointed its even better than the pictures. Absolutely perfect for a small family and dog. Screened porch and outside decks were great . Definitely a five star."
Blue Heron Cottage is cozy & convenient. Renovated March 2023!
Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing
9.8 out of 10, Exceptional, (122)
"Everything was perfect! Having a boat dock in backyard was awesome! Our hosts were awesome and very accommodating! Really didn’t need anything extra! To wake up walk out into screened porch for morning coffee and watch nature was perfect! We will definitely be back! "
Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing
Inviting and Serene Home on Monroe Bay Creek
10.0 out of 10, Exceptional, (61)
"Second time we've visited and both times were very enjoyable. Shannon is very communitive and does everything possible to make our stay perfect! Now if she could only control the weather.....! ;)"
Inviting and Serene Home on Monroe Bay Creek
Cheery, Peaceful Water Front Cabin on Winery Grounds
9.8 out of 10, Exceptional, (33)
"My wife and I visited for our anniversary and truly enjoyed our stay. Caught 11 bass "
The price is AU$429
includes taxes & fees
2 Oct - 3 Oct
Cheery, Peaceful Water Front Cabin on Winery Grounds
Waterfront Cottage in Beautiful Hoopers Island
10.0 out of 10, Exceptional, (61)
"We can't say enough good things about our long weekend stay! This was our first time in the area, and it was so quiet, peaceful, and beautiful. The views from the home were stunning, and everything was clean, welcoming, and bright—exactly what we needed for a little getaway. My husband and our dogs absolutely loved it. We spent most of our time outdoors, but when we were inside, the home was cozy, warm, and comforting. We slept great every night. The host was communicative and helpful, and we...
Waterfront Cottage in Beautiful Hoopers Island
Cozy Virginia Potomac Riverfront Cottage
9.8 out of 10, Exceptional, (32)
"Communication was prompt. Cottage was clean. The views were spectacular. I would stay again."
Cozy Virginia Potomac Riverfront Cottage
The Schultz Estate
9.2 out of 10, Wonderful, (13)
"What a wonderful stay we had! The house was so comfortable with plenty of space for everyone to relax and enjoy each other's company. We enjoyed the brisk mornings on the porch and the gorgeous sunsets in the evenings. Very comfortable beds and linens. The scenery and landscape in the area are breathtaking. Every turn provided another incredible view of the water. Fishing Creek is close to so many beautiful, quaint towns along the Chesapeake Bay. Highly recommend!"
The Schultz Estate
**FAMILY FRIENDLY CREEKSIDE GETAWAY - HIDEAWAY AND ENJOY THE FAMILY MOMENTS**
10.0 out of 10, Exceptional, (179)
"Beautiful property and views. Lots of birds in the area including Bald Eagles. Very relaxing to sit on the dock or on the deck or around the fire pit area. The house has a ramp to go in the back of the house. Showers are all step-in. Bedrooms have enough room to move around in with a walker or a wheelchair. The house is not cluttered with things so there was a lot of room for wheelchairs. The only challenge we had was getting over the sliding glass door track in the wheelchairs. We used...
**FAMILY FRIENDLY CREEKSIDE GETAWAY - HIDEAWAY AND ENJOY THE FAMILY MOMENTS**
Relax & Renew in a WATERFRONT Cottage , private pier, kayaks, fishing, wineries.
10.0 out of 10, Exceptional, (46)
"The home is beautifully decorated. They have so much to do inside and out. They provided something for everyone. This is our 2nd year here. We plan to come back."
Relax & Renew in a WATERFRONT Cottage , private pier, kayaks, fishing, wineries.
Soul Oasis - home on the Chesapeake Bay
9.8 out of 10, Exceptional, (15)
"The private beach is beautiful. Neighborhood is nice and quiet. Enjoyed our stay."
The price is AU$460
includes taxes & fees
1 Oct - 2 Oct
Soul Oasis - home on the Chesapeake Bay
Maryland Vacation Rental w/ Private Pool & Dock
10.0 out of 10, Exceptional, (5)
"We enjoyed our time in Lusby. There was enough room for our family of four. The kitchen was well stocked and it was nice having a gas grill. My husband enjoyed trying to catch fish off the dock. He did manage to get two crabs. We spent most of our time in the pool and relaxing on the deck. The house is located near several grocery stores and restaurants."
Maryland Vacation Rental w/ Private Pool & Dock
Private Beach Front Getaway at The Sunshine Beach Cottage.
9.8 out of 10, Exceptional, (61)
"The Bay is beautiful, and to enjoy it from this property all you have to do is open the door and step onto the porch. That puts you within 20 feet or so of the water's edge. The chaises can be brought onto the sand for an ideal beach day in the sun. The house is squeezed in tightly between two others, but there are only two properties to the south and then several hundred yards of open beach; so there's room to spread out if that's important. The house has everything you could need or want and...
Private Beach Front Getaway at The Sunshine Beach Cottage.
Waterfront Relaxing Getaway
9.8 out of 10, Exceptional, (18)
"Nice house, beautiful waterfront property, great host. No complaints whatsoever, highly recommend. "
Waterfront Relaxing Getaway
Bay view from Calvert Cliffs, Solomons Island & State Park nearby
10.0 out of 10, Exceptional, (36)
"We had a great time on vacation. Loved everything about the house - had everything we needed and we really enjoyed exploring the area. "
Bay view from Calvert Cliffs, Solomons Island & State Park nearby
Peace & Tranquile waterfront home, Colonial Beach
9.6 out of 10, Exceptional, (15)
"Great location"
Peace & Tranquile waterfront home, Colonial Beach
Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp
9.8 out of 10, Exceptional, (56)
"Our group of 6 guys who have been friends since elementary school (all 60+ years old now) enjoyed another great annual visit to Cove House. Fish and crabs were biting. Sunsets and rainbows lit up the sky. And good friends reconnected, laughed, and enjoyed being away from the world for a bit. We will be calling again!"
Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp
Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier
9.8 out of 10, Exceptional, (107)
"What a cool house - awesome views of Chesapeake. private beach, private pier and kayaks! what more can you ask for? Awesome!"
Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier
Chic Cottage w/ Private Yard: Steps to Beach!
10.0 out of 10, Exceptional, (16)
"Cute property, well-maintained, great location, an absolutely relaxing weekend. We’ll be back!"
Chic Cottage w/ Private Yard: Steps to Beach!
Large Luxury 4 bed/3 bath Beach House-2 Blocks to beach, 1 Block to Bay
10.0 out of 10, Exceptional, (43)
"Great time! First time in Colonial Beach. Low key family time. House was perfect location for us. Very enjoyable!"
Large Luxury 4 bed/3 bath Beach House-2 Blocks to beach, 1 Block to Bay
Waterfront Lusby Retreat w/ Deep-Water Dock & Slip
9.8 out of 10, Exceptional, (10)
"We stayed for a quick weekend during a celebration of life. We enjoyed the ample communal space. Our only complaint was the lack of dog friendly space for potty breaks and there were quite a few things with notes that were broken around the house. "
Waterfront Lusby Retreat w/ Deep-Water Dock & Slip
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Other types of properties in Leonardtown you may be interested in

The Inn at Leonardtown, Ascend Hotel Collection
2.5 star property
9.0 out of 10, Wonderful, (107)
"Great location and very clean. Spacious room."
The price is AU$179
includes taxes & fees
17 Oct - 18 Oct
The Inn at Leonardtown, Ascend Hotel Collection
La Quinta Inn & Suites by Wyndham Lexington Park - Patuxent
2.5 star property
7.6 out of 10, Good, (1003)
"Staff was friendly and room was clean and comfortable."
The price is AU$149
includes taxes & fees
3 Oct - 4 Oct
La Quinta Inn & Suites by Wyndham Lexington Park - Patuxent
River Edge Inn
2.5 star property
8.2 out of 10, Very good, (239)
"Older hotel right on the beach with side window views. No balcony on the river but exterior benches on the parking lot side. Direct access to the board walk. Decent breakfast. Good stay, basic hotel with modest amenities. Great location for a low key beach setting."
The price is AU$195
includes taxes & fees
13 Oct - 14 Oct
River Edge Inn
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.

Frequently asked questions

Are there holiday rentals in Leonardtown?

Yes, there are holiday rentals close to the most popular sights in Leonardtown, or you can select a more secluded option if you're looking for a relaxing stay. 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 holiday rentals that Leonardtown has to offer?

The Schultz Estate : This holiday home rental outside of Leonardtown offers a patio, a selection of games and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

How many holiday rentals will I find in Leonardtown?

With 10 Expedia holiday rentals, you're guaranteed 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 New Towne Neck State Park are a couple of lovely local spots to get outside and enjoy nature. Port of Leonardtown Winery and Patuxent River Naval Air Station are a couple of places you'll find in the wider area.

What’s a holiday rental in Leonardtown like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Leonardtown. Holiday rentals provide amenities such as patios, hot tubs and fire pits so you'll feel just like you're at home. If you're concerned about a sanitised environment, a holiday rental can offer a sense of privacy away from public hotel lifts and busy front desks while still allowing you to travel. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a great choice for a family trip or a small group gathering.