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Compare 97 Cottages in Leonardtown with updated reviews, rates, and availability.

Property grounds
Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing
9.8 out of 10, Exceptional, (107)
"The property is located in a small neighborhood right by the water. While there are houses fairly close it is quiet with beautiful views. The house is clean and has good appliances/wifi for a comfortable stay. It is a one bedroom with a big bathroom and living room. The screened in patio is good to avoid the mosquitos. One note is for those with mobility issues, the shower/bathtub has a high ledge with a thicker width to get in/out."
The price is $165
$258 total
includes taxes & fees
May 28 - May 29
Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing
Fridge, microwave, stovetop, dishwasher
'The Blue Crab Cottage' - 3 Blocks From The Beach!
9.8 out of 10, Exceptional, (57)
"Stay was good. Neighbors not so much"
'The Blue Crab Cottage' - 3 Blocks From The Beach!
Property grounds
Waterfront Cottage in Beautiful Hoopers Island
10.0 out of 10, Exceptional, (54)
"We have stayed at this property twice and love it. Very peaceful, clean, and comfortable."
Waterfront Cottage in Beautiful Hoopers Island
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On the beach, sun loungers, beach towels
Private Beach Front Getaway at The Sunshine Beach Cottage.
9.8 out of 10, Exceptional, (45)
"My husband and I have been to this cottage once before. It's our secret getaway. It has everything you need plus the beach is just a few feet away. You can't find another place like this one!"
Private Beach Front Getaway at The Sunshine Beach Cottage.
Beach nearby, sun loungers, beach towels
Relax & Renew in a WATERFRONT Cottage , private pier, kayaks, fishing, wineries.
10.0 out of 10, Exceptional, (36)
"Beautiful Bay view and pier access. Super clean, comfortable and attractive cottage with TONS of activity equipment in the finished and screened in lower level. Great for kids and teens but anyone would enjoy! Pet friendly, too! Highly recommend."
Relax & Renew in a WATERFRONT Cottage , private pier, kayaks, fishing, wineries.
Property 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!
Beach
Cozy Virginia Potomac Riverfront Cottage
9.6 out of 10, Exceptional, (23)
"We were in the area for a family wedding so spent most of our time away from the cottage. It provided a welcome morning and evening retreat, sun (or even clouds) over the water. We could have enjoyed many hours sitting in the "sun room" if we hadn't been pulled away to other activities. It was all lovely and easy. Suggest owners install a grab bar for the tub/shower. That tile step is dangerous, especially when wet."
Cozy Virginia Potomac Riverfront Cottage
Exterior
Soul Oasis - home on the Chesapeake Bay
10.0 out of 10, Exceptional, (6)
"Pleasant relaxing time. We were pleased and impress to locate this property"
The price is $130
$285 total
includes taxes & fees
May 27 - May 28
Soul Oasis - home on the Chesapeake Bay
Smart TV, books
Rodo Beach Cottage - Dog Friendly Private Beach with Pier - Tesla Charger
9.8 out of 10, Exceptional, (9)
"The cozy house make our weekend great! Nice view, we enjoyed kayak."
Rodo Beach Cottage - Dog Friendly Private Beach with Pier - Tesla Charger
Beach/ocean view
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
TV, fireplace, books
Waterfront Cottage w/ Private Beach + Deck!
9.8 out of 10, Exceptional, (12)
"First class Property excellent furnishings, well supplied, lovely view everything top of the line"
Waterfront Cottage w/ Private Beach + Deck!
Beach nearby
Cozy Cottage with access to and partially obstructed views of the bay.
9.2 out of 10, Wonderful, (10)
"We had a wonderful stay at this cute yellow house by the bay. It has all the comforts of home. It was perfect for family time. We would definitely stay here again."
Cozy Cottage with access to and partially obstructed views of the bay.
Property grounds
Adorable Cottage: Fire Pit, Walk to Colonial Beach
10.0 out of 10, Exceptional, (2)
"A wonderful home with lots of room in a great location. Lots of care taken to make guests comfortable and that they will feel at home! Very walkable. Thoroughly enjoyable! Would definitely book again!"
Adorable Cottage: Fire Pit, Walk to Colonial Beach
On the beach
Refreshing Colonial Beach Vacation Rental!
10.0 out of 10, Exceptional, (9)
"Our stay at the Shore Cottage was everything we could have wanted and more. The home is beautifully appointed and impeccably maintained. Everything was fresh and clean and very comfortable. We enjoyed the amenities of the gazebo overlooking the water and our boys spent endless hours playing in the sand and water. Just a short car trip to restaurants and attractions, very manageable. The hostess, Marilyn, is very sweet and extremely helpful and accomodating. Can't beat coffee in the gazebo...
Refreshing Colonial Beach Vacation Rental!
Beach nearby, sun loungers, beach towels
WATERFRONT GETAWAY- Charming Waterfront Cottage on St Clements Bay
10.0 out of 10, Exceptional, (52)
"We enjoyed out stay very much in February. It was so quiet and nice. Very very clean! Three generations of family came and loved. The sunroom with the view of the water was amazing and nice and toasty for our winter getaway. Thank you Diane and Harold for being so helpful, all the extra nice touches you added, and sharing your lovely cottage with us! We would love to visit again."
WATERFRONT GETAWAY- Charming Waterfront Cottage on St Clements Bay
Cookware/dishes/utensils
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!
Interior
Chic Cottage w/ Private Yard: Steps to Beach!
3.0 star property
10.0 out of 10, Exceptional, (2)
"The cottage is an older structure that has been impeccably renovated. It had everything we needed for a week's stay. Colonial Beach is not a glamorous ocean holiday destination. It is a rural community with a basic infrastructure on the Potomac River."
Chic Cottage w/ Private Yard: Steps to Beach!
View from property
Chesapeake Bay Vacation Rental w/ Boat Dock!
9.0 out of 10, Wonderful, (4)
"Would go back today if we could. 12/10"
Chesapeake Bay Vacation Rental w/ Boat Dock!
Fridge, microwave, stovetop, coffee/tea maker
Chic Cottage w/ Private Yard: Steps to Beach!
9.8 out of 10, Exceptional, (10)
"Wonderful home, courteous home owner, excellent customer service through Evolve. The home was clean and comfortable with all of the little extras you might need when traveling or you may have forgotten. The design of the home was a great use of space and really cozy beach vibes. The porch and backyard areas were a fun surprise and my little dog did not want to leave the porch. Colonial Beach has many great restaurants and home has convenient access to beautiful river beaches and bayside...
Chic Cottage w/ Private Yard: Steps to Beach!
Interior
Hays Beach House - Hot Tub - Private Beach
10.0 out of 10, Exceptional, (1)
"This is our 16th year vacationing at Hay Beach, but our first time staying at this property. The house is very confrontable and the layout is great, plenty of room for our family, 3 couples. The second level deck was the hangout, beautiful views of the sun rises with morning coffee, watching large pods of dolphins swimming 30 yards off the beach, eagles flying overhead and cocktails every evening. The guys fished from kayaks while the girls laid in the sun on the deck every day ... great...
Hays Beach House - Hot Tub - Private Beach
Don't see what you're looking for?
See all available properties in Leonardtown
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

Smart TV, fireplace
Gorgeous Sunsets & Waves Heard From Bed. Why Wait?
8.8 out of 10, Excellent, (3)
"The curb appeal and overall condition of the property is not what we expected. There was a large construction crane and debris in the yard and the landscaping was not maintained. The bed sheets were not fitting the bed and the beds were not comfortable. The back yard had new grass growing with a net on the ground which is a tripping hazard. The view and sounds of the water was great but there is a steep drop off to the water with no fence or railing. For the price paid we expected a lot more."
The price is $320
$559 total
includes taxes & fees
May 31 - Jun 1
Gorgeous Sunsets & Waves Heard From Bed. Why Wait?
Property 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!
TV, fireplace, DVD player, books
Peaceful Water Front Cabin on Winery Grounds
9.8 out of 10, Exceptional, (23)
"The property is easy to access and the house is filled with natural light from the huge windows. It’s a wonderful getaway if you want to unplug and enjoy a cozy few days of quiet. We found a waterfront Mexican restaurant nearby and walked to the winery next door. It’s very clean and the host is very responsive if you have any questions. Loved drinking coffee on the deck while enjoying the peaceful pond view. Left relaxed and refreshed!"
The price is $109
$259 total
includes taxes & fees
Jun 6 - Jun 7
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.

Leonardtown Cottages information

Number of reviews
453
Accommodation
97 Cottages
Lowest Price
$130
Highest Price
$165

Frequently asked questions

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What is there to do in Leonardtown near my cottage?
You’ll find plenty of fun things to do in Leonardtown. Discover popular attractions like St. Marys River State Park, Port of Leonardtown Winery and St. Clements Island State Park. New Towne Neck State Park, Greenwell State Park and Sotterley Plantation are also on many to-do lists.

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