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Compare 94 Cottages in Leonardtown with updated reviews, rates, and availability.

Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing

9.8 out of 10, Exceptional, (124)
"We chose to celebrate our 10th wedding anniversary here for a quiet weekend away with our dog. The house provided everything we needed and the owners were great to deal with. Highly recommend!! "
Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing

Blue Heron Cottage is cozy & convenient. Renovated March 2023!

10.0 out of 10, Exceptional, (38)
"Heather and Ed are superb hosts. The home was very clean, well stocked and in the perfect location! "
Blue Heron Cottage is cozy & convenient. Renovated March 2023!

Soul Oasis - home on the Chesapeake Bay

9.8 out of 10, Exceptional, (17)
"Beautiful and quiet in the fall. A great place for relaxing. Clean, great communication. End of the street with views of the bay. "
The price is SAR 563
SAR 1,166 total
includes taxes & fees
1 Dec - 2 Dec
Soul Oasis - home on the Chesapeake Bay

Chic Cottage w/ Private Yard: Steps to Beach!

10.0 out of 10, Exceptional, (16)
"Amazing use of square footage to provide everything a couple could use for a getaway. Owners have great taste and decorations give it a beach vibe. Conveniently located at the Point and walking distance to bars and restaurants. Would stay here again."
Chic Cottage w/ Private Yard: Steps to Beach!

Cozy Virginia Potomac Riverfront Cottage

9.8 out of 10, Exceptional, (34)
"This is a nice little cottage, tucked away from everything right on the river. I was looking for some peace and quiet, and that’s exactly what I got. Even though the weather wasn’t great, the sunroom still let me enjoy the views. "
Cozy Virginia Potomac Riverfront Cottage

Off-season prices! Waterfront Cottage on Hoopers Island. Pet friendly. 🏝️🦀🎣

10.0 out of 10, Exceptional, (46)
"Great experience, wonderful cozy cottage with thoughtful touches throughout. Remote, peaceful location with excellent fishing and crabbing all around you. Fantastic eating at Old Salty's less than a couple of miles away. Very dog friendly cottage and lovely screened in porch area to sit and watch the sunsets. We will be booking again next year."
Off-season prices! Waterfront Cottage on Hoopers Island. Pet friendly. 🏝️🦀🎣

Waterfront Cottage w/ Private Beach + Deck!

9.8 out of 10, Exceptional, (15)
"Beautiful place and very peaceful stay!"
Waterfront Cottage w/ Private Beach + Deck!

Cozy Cottage with access to and partially obstructed views of the bay.

9.4 out of 10, Exceptional, (13)
"Away from the hustle and bustle of any city but close enough to get anything you need. Our stay was very relaxing and Hyrum and Lisa were the best hosts we have had so far... Will definitely look for them again if we are in the area again..."
Cozy Cottage with access to and partially obstructed views of the bay.

2 Bedroom Cozy Beach Cottage with Beach Access

10.0 out of 10, Exceptional, (10)
"This was the perfect cottage for our family's fall getaway to St. Mary's! The host was wonderfully communicative and the cottage was perfectly appointed for our little get away. We will definitely be back!"
2 Bedroom Cozy Beach Cottage with Beach Access

Sunrise Waterfront Cottage with Dock & Kayaks!

9.6 out of 10, Exceptional, (20)
"We had a great time here. The property was exactly what we were looking for. It was remote and quite. We loved the dock and water access. We fished off the dock two days. Pulled in a couple of medium sized Red fish and a few other smaller varieties. This would be a great fishing spot with small kids. Beds were super comfortable. "
Sunrise Waterfront Cottage with Dock & Kayaks!

Perfect gift•Game Theme•Dock+Boat+King bd+EV Chrgr

10.0 out of 10, Exceptional, (17)
"Great location love the waterfront , quiet peaceful, well decorated game themed hone - kids enjoyed it, use kayak and supplies is a plus - enjoyed kayak rides and outdoor space "
The price is SAR 736
SAR 1,579 total
includes taxes & fees
8 Dec - 9 Dec
Perfect gift•Game Theme•Dock+Boat+King bd+EV Chrgr

Waterfront Cottage in Beautiful Hoopers Island

10.0 out of 10, Exceptional, (63)
"My boyfriend and I needed to get away. This house and location was just what we needed. Beautiful scenery, cozy home. We started a full week and I was sad to go at the end of our trip. We look forward to visiting again in the future! "
Waterfront Cottage in Beautiful Hoopers Island

Private Beach Front Getaway at The Sunshine Beach Cottage.

9.8 out of 10, Exceptional, (63)
"Beautifully appointed cottage. Literally right on the water. Quiet, serene and relaxing. Loved it and will be back!"
Private Beach Front Getaway at The Sunshine Beach Cottage.

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

10.0 out of 10, Exceptional, (50)
"We had a chance to spend the weekend with our kids (age 18 and 20), and we couldn't have asked for a better location. The view was spectacular and the home was perfect. It was so peaceful and relaxing, yet there was so much to do—fishing, kayaking, paddleboarding, ping-pong, darts, board games, the list goes on. Everyone had a fantastic time. The only problem is that were only there for three nights!"
Relax & Renew in a WATERFRONT Cottage , private pier, kayaks, fishing, wineries.

'The Blue Crab Cottage' - 3 Blocks From The Beach!

9.8 out of 10, Exceptional, (65)
"Love love this place! Clean and close to everything. We had a great time. I think I stayed there more than going out 😉"
'The Blue Crab Cottage' - 3 Blocks From The Beach!

Hays Beach House - Hot Tub - Private Beach

10.0 out of 10, Exceptional, (4)
"We booked this bayside property for a short family vacation and the house and amenities were exactly what we needed during our time at Hays Beach. There were ample bedrooms and spaces for all of us to relax, the kitchen was well appointed. The beach in front of the house was perfect for our grandson to play in a small pool while the others lounged in chairs or were in the water directly in front of the house. The public beach was a short walk away and we enjoyed seeing all the wildlife on the...
Hays Beach House - Hot Tub - Private Beach

Waterfront Cottage in Piney Point w/ Kayaks!

7.6 out of 10, Good, (4)
"First, this was a last minute booking, due to our inability to stay at our original rental. Becky was responsive to our needs so we could vacate our previous rental without delay. Next, what I loved about this property, and something you do not get very often is the amount of living, relaxing space there is in this rental. Several areas for groups of people to spread out, watch TV, look at the water, play games, often times while there are several bedrooms, there are precious few places for...
Waterfront Cottage in Piney Point w/ Kayaks!

Piney Point, private , Beach Front Cottage

10.0 out of 10, Exceptional, (86)
"This house is beautiful and has everything anyone could ask for. The scenery is spectacular too. We enjoyed sitting outside watching the sun set, just listening to the water and enjoying a fire on the beach. The kitchen is any cook's dream! The owners are wonderful and communicated with us wonderfully. We would give it a 10 rating if possible and will certainly be back. One of our best vacations!"
Piney Point, private , Beach Front Cottage

Scenic Sunsets star lite sky between Pax River and Wash DC. Experiences Await!

10.0 out of 10, Exceptional, (4)
"What a wonderful quick getaway weekend from DC! The quiet neighborhood, front row river views, and wonderful hospitality was unmatched! What a great way to get to know St Mary’s County!"
Scenic Sunsets star lite sky between Pax River and Wash DC. Experiences Await!

Rodo Beach Cottage - Dog Friendly Private Beach with Pier - Tesla Charger

10.0 out of 10, Exceptional, (14)
"My husband and I and our grown kids and dog stayed for 3 weeks at Rodo Beach House. The weather was mostly beautiful. The house is lovely and had everything we needed, including comfy beds! The owner is friendly and easy to contact. We had great fires in the firepit. Comfortable outside chairs around the fire pit as well as on the beach. The bay is incredibly clean, and the small private beach is perfect for people and dogs. The neighborhood, beach and surroundings are private, quiet and...
Rodo Beach Cottage - Dog Friendly Private Beach with Pier - Tesla Charger
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

Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing

9.8 out of 10, Exceptional, (124)
"We chose to celebrate our 10th wedding anniversary here for a quiet weekend away with our dog. The house provided everything we needed and the owners were great to deal with. Highly recommend!! "
Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing

Blue Heron Cottage is cozy & convenient. Renovated March 2023!

10.0 out of 10, Exceptional, (38)
"Heather and Ed are superb hosts. The home was very clean, well stocked and in the perfect location! "
Blue Heron Cottage is cozy & convenient. Renovated March 2023!

Cheery, Peaceful Water Front Cabin on Winery Grounds

9.8 out of 10, Exceptional, (36)
"Such a cute rustic cabin with all the comforting details in all aspects! Nothing left out! Right next door to a winery a walk away… the perfect country fall getaway! We will definitely be back! It was a delightful location!"
The price is SAR 454
SAR 1,017 total
includes taxes & fees
3 Dec - 4 Dec
Cheery, Peaceful Water Front Cabin on Winery Grounds
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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