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Leonardtown Vacation Rentals

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Browse Select Leonardtown Vacation Homes

Waterfront Paradise with Pool & Hot Tub plus 4 King Beds & 4 Full baths
10.0 out of 10, Exceptional, (71)
"We had an incredible stay at this beautiful VRBO home! The property itself is nothing short of stunning, with a magnificent view of the river that we enjoyed every morning. The pool was fabulous, perfect for relaxing and having fun with our family. The house was extremely comfortable, spotlessly clean, and fully equipped with everything we needed for a perfect vacation. Every detail was thoughtfully considered, making it feel like a true home away from home. There were plenty of fun and...
Waterfront Paradise with Pool & Hot Tub plus 4 King Beds & 4 Full baths
Inviting and Serene Home on Monroe Bay Creek
10.0 out of 10, Exceptional, (60)
"Perfect location just minutes from colonial beach. The house every amenity one could want and gets amazing views over the water. This is our second time there this year alone and we plan to return again next year!"
Inviting and Serene Home on Monroe Bay Creek
Quiet Oasis for the Whole Fam, Relax On The Porch Or 1 Minute Walk to the Beach!
10.0 out of 10, Exceptional, (139)
"Very spacious for 6-7 ladies. Some limitations due to steps. 3 bedrooms first level but 2 bedrooms up very narrow farmhouse stairway and not good if physical issues. "
Quiet Oasis for the Whole Fam, Relax On The Porch Or 1 Minute Walk to the Beach!
Peace & Tranquile waterfront home, Colonial Beach
9.6 out of 10, Exceptional, (15)
"Great location"
Peace & Tranquile waterfront home, Colonial Beach
Waterfront with spectacular view, close to restaurants and bars
10.0 out of 10, Exceptional, (28)
"Clean, spacious, comfortable inside and out, great amenities, great sunset views, coffee pods, water, snacks - my best friend and I were able to truly relax for the weekend. We will reserve this home again!"
Waterfront with spectacular view, close to restaurants and bars
Picture Perfect Waterfront in town Sleeps 6 Expansive Outdoor dining area
10.0 out of 10, Exceptional, (20)
"This property exceeded any expectation I had. The view really is picture perfect. The deck is amazing and we spent a lot of time out there. The inside is equally impressive - beautiful decor, big kitchen with all you need, huge TV! We can’t wait to go back. "
Picture Perfect Waterfront in town Sleeps 6 Expansive Outdoor dining area
WATERFRONT!!! The River's Roost on The Patuxent River
10.0 out of 10, Exceptional, (15)
"Great place with lots of room. Very relaxing and a great host"
WATERFRONT!!! The River's Roost on The Patuxent River
Colonial Beach Cottage, 7 minutes walk to beach!
9.6 out of 10, Exceptional, (19)
"Great place, plenty of room"
Colonial Beach Cottage, 7 minutes walk to beach!
Cozy Catalina Cabin
10.0 out of 10, Exceptional, (16)
"Great place, clean, quiet area "
Cozy Catalina Cabin
Secluded waterfront house to relax or enjoy water activities from private pier
9.8 out of 10, Exceptional, (25)
"Overall very pleased. Seemed like a lot of money for the property but I guess that’s what waterfront cost. House was very clean and well equipped. Loved the mini-splits in each room. The only reason I gave “cleanliness” four stars is because the outside trash can had a bunch of trash the smelled horrible and the recycling container also had trash in it. Michelle was great and very responsive. There’s a great market on the island but very few dining options and no fine dining. Very cozy...
Secluded waterfront house to relax or enjoy water activities from private pier
Beachy Maryland A-Frame: Steps to Chesapeake Bay!
9.6 out of 10, Exceptional, (5)
"We loved having a little bay beach in our backyard! We brought floats and a blow up pool, we swam and jumped of the dock at high tide. The kids fished of the pier and we relaxed by the fire pit. Excellent relaxing secluded long weekend. Dinner outside at Salt kitchen nearby was delicious! "
Beachy Maryland A-Frame: Steps to Chesapeake Bay!
Single family home with screened porch.
10.0 out of 10, Exceptional, (7)
"This was our 4th stay at Fishing Creek. Kelli's property was by far the most comfortable and well appointed. The kitchen was incredibly well-stocked. There was a complimentary bottle of wine on the kitchen table, drinks, coffee, hot chocolate, everything needed to make s'mores. The game room was a hit with the kids, and my husband and I enjoyed our morning coffee in the screened in sunroom. Wish we could have stayed longer. Would love to stay here again the next time we are on Hoopers...
Single family home with screened porch.
Blue Heron Retreat on the Water
10.0 out of 10, Exceptional, (9)
"We had a relaxing stay at the Blue Heron Retreat. The house is as described. The beds were very comfortable and it was nice sitting out on the decks having our morning coffee and listening to the birds. We used the hot tub every day since it’s shaded by trees so even though we had hot weather, we were still able to use it during the day. "
Blue Heron Retreat on the Water
4BDRM River front house with Private Beach in Hollywood
2.0 star property
9.6 out of 10, Exceptional, (4)
"My father passed away in the Hollywood area and we had a large group of family and friends wanting to attend the services. We used this wonderful property for many of our family to stay together. The property was peaceful and beautiful which is exactly what we needed. The house was wonderfully stocked and in a beautiful peaceful location."
4BDRM River front house with Private Beach in Hollywood
Historic charm with modern amenities
2.0 star property
10.0 out of 10, Exceptional, (1)
"The room we stayed in had a separate bedroom, living room and bathroom. Oversized refrigerator was handy. Will definitely stay here again."
The price is CA $214
CA $242 total
includes taxes & fees
Oct 4 - Oct 5
Historic charm with modern amenities
Charming 1-bedroom house with AC and WiFi in quaint Montross
10.0 out of 10, Exceptional, (1)
"Everything was lovely! "
Charming 1-bedroom house with AC and WiFi in quaint Montross
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
**FAMILY FRIENDLY CREEKSIDE GETAWAY - HIDEAWAY AND ENJOY THE FAMILY MOMENTS**
10.0 out of 10, Exceptional, (177)
"Enjoyed our mini vacation at Creekside Getaway, Thank you Ray for being a wonderful host and allowing us to stay at your house. House offers plenty of room, very clean, a lot of though in providing items in the house and outside to make our stay very comfortable. Grounds are beautiful, spacious, very quiet, had the riverfront all to ourselves. Enjoyed kayaking seeing plenty of nature. A great stay and highly recommended!"
**FAMILY FRIENDLY CREEKSIDE GETAWAY - HIDEAWAY AND ENJOY THE FAMILY MOMENTS**
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
Potomac Waterfront Retreat w/ Dock & Kayaks
9.0 out of 10, Wonderful, (4)
"My husband I just stayed at this charming home two weeks ago. The house was absolutely perfect--very open inside with a spectacular pier and view of the Potomac and Chesapeake Bay. Point Lookout (Maryland) is directly across the river. There were a few towns around with galleries, splash pads, parks, shopping but it's not the kind of vacation where you run from attraction to attraction all day. Our"
Potomac Waterfront Retreat w/ Dock & Kayaks
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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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Other property types in Leonardtown

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.
Blue Heron Cottage is cozy & convenient. Renovated March 2023!
10.0 out of 10, Exceptional, (31)
"The Blue Heron Cottage was an excellent stay for my family. While small, the property was big enough for us and two kids. The cottage itself inside was pretty new all around. The only thing that needs updating would be the shower. Full kitchen with oven and fridge was nice. Beds comfy. Property good for kids and a dog if you have one. The best part was the location. A block from the bay and three from the river. We would definitely stay here again. Thank you for having us!"
Blue Heron Cottage is cozy & convenient. Renovated March 2023!
Cozy Virginia Potomac Riverfront Cottage
9.8 out of 10, Exceptional, (31)
"Clean, comfortable, quiet, and what a beautiful spot on the river! Thank you 😊 "
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.