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Search Cottages in Leonardtown

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Compare 98 Cottages in Leonardtown with updated reviews, rates, and availability.

Blue Heron Cottage is cozy & convenient. Renovated March 2023!
10.0 out of 10, Exceptional, (22)
"We enjoyed our stay. The cottage was perfect for our get away. It was clean and had everything we needed. The owners are very responsive to any questions."
Blue Heron Cottage is cozy & convenient. Renovated March 2023!
Private Beach Front Getaway at The Sunshine Beach Cottage.
9.8 out of 10, Exceptional, (50)
"Beautiful little house right on the beach of the Chesapeake. Loved it. Everything was great and we will definitely be back!"
Private Beach Front Getaway at The Sunshine Beach Cottage.
Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing
9.8 out of 10, Exceptional, (108)
"What a nice spot to unplug and relax! Waterfront property in a super quiet neighborhood. Hosts live next door; friendly and helpful, excellent communication. House was spotless, bed and furniture was comfortable, kitchen was all set up, spacious bathroom. There is a great screened porch that we spent most of our time on. Lots of wildlife to watch. Dog friendly with a big lot to enjoy. They have a nice grill and a fire pit. We also enjoyed a great dinner at Captain Billy's Crab House. Will be...
Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing
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Waterfront Cottage in Beautiful Hoopers Island
10.0 out of 10, Exceptional, (55)
"Very clean small cottage in a beautiful spot. I was able to swim off the dock. There was plenty of outdoor space with comfortable Adirondack chairs. Very quiet at night and the beds were comfortable. Our host was most kind."
Waterfront Cottage in Beautiful Hoopers Island
Cozy Virginia Potomac Riverfront Cottage
9.6 out of 10, Exceptional, (24)
"We had a wonderful stay. The house was just as described, a cozy cottage perfect for relaxing with beautiful riverfront views. The kitchen was stocked with everything we needed, the living room and main bedroom we used were comfortable, and the sun porch had great views where you could relax in the AC. The patio had a great dining table/umbrella, and the dock was perfect for fishing. Thank you for a lovely getaway cottage!"
Cozy Virginia Potomac Riverfront Cottage
Chesapeake Bay Vacation Rental w/ Boat Dock!
9.0 out of 10, Wonderful, (6)
"It was not as clean as it should have been. When i pay to stay somewhere, i expect clean."
Chesapeake Bay Vacation Rental w/ Boat Dock!
Soul Oasis - home on the Chesapeake Bay
10.0 out of 10, Exceptional, (8)
"we really, really like the retro look and really enjoyed the space. It was quiet and we were able to relax."
The price is SAR 563
SAR 1,165 total
includes taxes & fees
28 Jul - 29 Jul
Soul Oasis - home on the Chesapeake Bay
Piney Point, private , Beach Front Cottage
10.0 out of 10, Exceptional, (77)
"The place was super clean, cozy and had everything we needed. Beautiful place to relax and enjoy the water. Nick was responsive and we even had a nice treat waiting for us when we arrived. Would definitely stay again!"
Piney Point, private , Beach Front Cottage
Cozy Cottage with access to and partially obstructed views of the bay.
9.4 out of 10, Exceptional, (12)
"This was a great little getaway! The property was very accurate to the listing, and everything was very clean and tidy. We cooked a bit at the house and it had all the pots/pans/utensils we needed. The beach across the street is quite nice, and it's a short drive to Calvert Cliffs State Park. Would definitely recommend this VRBO!"
Cozy Cottage with access to and partially obstructed views of the bay.
Adorable Cottage: Fire Pit, Walk to Colonial Beach
10.0 out of 10, Exceptional, (3)
"This was our first time at Colonial Beach. The house was just perfect for us. Very spacious and clean. The host was very kind and helpful. The beach was literally 2/3 minutes walk away. We enjoyed the beautiful backyard at night."
Adorable Cottage: Fire Pit, Walk to Colonial Beach
Riverfront Newburg Cottage w/ Deck & Gas Grill!
10.0 out of 10, Exceptional, (1)
"Secluded cottage on the water. The host were fantastic. The view from the cottage is beautiful looking at the water and the birds. My sons brought their kayaking gear and kayak on the water. Just a great place to relax and get away from the hustle and bustle."
Riverfront Newburg Cottage w/ Deck & Gas Grill!
Relax & Renew in a WATERFRONT Cottage , private pier, kayaks, fishing, wineries.
10.0 out of 10, Exceptional, (37)
"Great place to stay with a fantastic view. Kids loved all the activities to do at the home and property manager was wonderful to deal with and even went over the top with the welcome sign with our name on it. Highly recommend!"
Relax & Renew in a WATERFRONT Cottage , private pier, kayaks, fishing, wineries.
Waterfront Cottage w/ Private Beach + Deck!
9.8 out of 10, Exceptional, (13)
"Beautiful place! Property manager was fantastic. Picture perfect views of water"
Waterfront Cottage w/ Private Beach + Deck!
Waterfront Cottage On Candy Point: Family-Friendly and Dog-Friendly!
9.6 out of 10, Exceptional, (116)
"This property has stunning views of the water- a super host and an impeccable cottage that was a delight to stay in. We’re already planning our return. Swim in the river, relax on the dog or grill local fish- this place is near perfection. Very clean. Everything you need and a sweet charming cottage that’s been beautifully preserved."
Waterfront Cottage On Candy Point: Family-Friendly and Dog-Friendly!
Charming cottage on Chesapeake Bay with private sand beach and 1 acre to play on
10.0 out of 10, Exceptional, (20)
"We loved the peace and comfort of this wonderful home! The neighborhood is really quiet and the view absolutely breathtaking. There was a small sandy beach with calm waters and we were able to catch crabs using their crab pots. Just wonderful!"
Charming cottage on Chesapeake Bay with private sand beach and 1 acre to play on
Chic Cottage w/ Private Yard: Steps to Beach!
3.0 star property
9.4 out of 10, Exceptional, (3)
"Very cute cottage with beach theme! "
Chic Cottage w/ Private Yard: Steps to Beach!
Sunnyside Up - Small Dog Friendly Waterfront Cottage
10.0 out of 10, Exceptional, (6)
"We had a wonderful long weekend and enjoyed everything this house had to offer. There were so many thoughtful details (fire pit, bikes, coffee, dog treats and on and on). We loved fishing off the dock and the fully fenced in yard was a huge hit for our fur baby. We can't say enough good things and would love to come back!"
Sunnyside Up - Small Dog Friendly Waterfront Cottage
Hays Beach House - Hot Tub - Private Beach
10.0 out of 10, Exceptional, (3)
"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
Sunrise Cottage on Hoopers Island. Fish, crab, boat, relax! Pet friendly.
10.0 out of 10, Exceptional, (42)
"My husband and I loved our visit to Sunrise Cottage! Everything was perfect and we can't wait to return."
Sunrise Cottage on Hoopers Island. Fish, crab, boat, relax! Pet friendly.
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!
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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.

Other property types in Leonardtown

Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing
9.8 out of 10, Exceptional, (108)
"What a nice spot to unplug and relax! Waterfront property in a super quiet neighborhood. Hosts live next door; friendly and helpful, excellent communication. House was spotless, bed and furniture was comfortable, kitchen was all set up, spacious bathroom. There is a great screened porch that we spent most of our time on. Lots of wildlife to watch. Dog friendly with a big lot to enjoy. They have a nice grill and a fire pit. We also enjoyed a great dinner at Captain Billy's Crab House. Will be...
Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing
Peaceful Water Front Cabin on Winery Grounds
9.8 out of 10, Exceptional, (24)
"Cabin was fantastic, area was very nice with a great view from the deck. Highly recommend!"
The price is SAR 409
SAR 972 total
includes taxes & fees
30 Jun - 1 Jul
Peaceful Water Front Cabin on Winery Grounds
Blue Heron Cottage is cozy & convenient. Renovated March 2023!
10.0 out of 10, Exceptional, (22)
"We enjoyed our stay. The cottage was perfect for our get away. It was clean and had everything we needed. The owners are very responsive to any questions."
Blue Heron Cottage is cozy & convenient. Renovated March 2023!
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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