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Compare 207 Vacation Homes in Leonardtown with updated reviews, rates, and availability.

Coan River Cottage w/ Fire Pit, Pool, Movie Room
Property grounds
Coan River Cottage w/ Fire Pit, Pool, Movie Room
10.0 out of 10, Exceptional, 2 reviews
"Jen was helpful and accommodating to our last minute requests."
Coan River Cottage w/ Fire Pit, Pool, Movie Room
Colonial Beach Cottage, 7 minutes walk to beach!
Fridge, microwave, oven, stovetop
Colonial Beach Cottage, 7 minutes walk to beach!
9.6 out of 10, Exceptional, 13 reviews
"This cottage was right on the main road in Colonial Beach. It was very clean and comfortable and tastefully decorated. The kitchen was fully equipped for cooking. The outdoor area was relaxing and had a fire pit and grill. The location was close to everything in town. You could walk to the beach and many stores and restaurants. We love the area and hope to return soon!"
Colonial Beach Cottage, 7 minutes walk to beach!
Shewell's A-Frame on Mill Creek
Exterior
Shewell's A-Frame on Mill Creek
10.0 out of 10, Exceptional, 1 review
"Beautiful home overlooking the water. Excellent communication with the owners who answered all of my questions quickly. No complaints at all and im Looking forward to returning soon."
Shewell's A-Frame on Mill Creek
Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp
Beach | Beach nearby, sun loungers
Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp
10.0 out of 10, Exceptional, 51 reviews
"What a fantastic property! We loved staying here and our family had such a great time exploring. Sadly it was a drizzly, dreary weekend but we had one nice day to go down to the beach and the kids enjoyed playing in the water. We loved the variety of porches to sit on and have different views and there was plenty of room for the kids to play indoors when it was raining. Overall a great experience. Thank you!"
Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp
Breathtaking Views, 450 pier, kayaks, fossils, priv beach, 45 min to D.C.
3 bedrooms, desk, iron/ironing board, free WiFi
Breathtaking Views, 450 pier, kayaks, fossils, priv beach, 45 min to D.C.
10.0 out of 10, Exceptional, 102 reviews
"Loved the house!"
Breathtaking Views, 450 pier, kayaks, fossils, priv beach, 45 min to D.C.
Waterfront Lusby Retreat w/ Deep-Water Dock & Slip
Beach
Waterfront Lusby Retreat w/ Deep-Water Dock & Slip
10.0 out of 10, Exceptional, 4 reviews
"We were in town for a friends wedding. This was the perfect location as it was right in between the Catholic Church for the nuptial mass and the reception site. This place certainly did not disappoint. There was plenty of space for our large family, the home was well equipped and stocked with the necessary items. It was a relatively short stay, but I wish we had a bit more time and better weather to enjoy the use of kayaks - our one free morning was a bit chilly for us Florida folks, and we had...
Waterfront Lusby Retreat w/ Deep-Water Dock & Slip
Waterfront with spectacular view, close to restaurants and bars
Property grounds
Waterfront with spectacular view, close to restaurants and bars
10.0 out of 10, Exceptional, 21 reviews
"This was our first time in Colonial Beach and we really enjoyed it. Definitely recommend renting a golf cart to get around town. The house is beautiful and in a great location close to everything. The homeowner was also great to work with and we’ll definitely be back soon!"
Waterfront with spectacular view, close to restaurants and bars
The Blue Crab is 5 blocks from Beach, 0.5 miles to Beach, 100 ft from bay.
Property grounds
The Blue Crab is 5 blocks from Beach, 0.5 miles to Beach, 100 ft from bay.
10.0 out of 10, Exceptional, 15 reviews
"The outdoor area with covered patio was very nice and pleasant even though the weather was quite hot. The proximity to the bay afforded a cooling breeze. Upon first approaching the property the area looked a bit sketchy but we hardly saw anyone and it was very quiet."
The Blue Crab is 5 blocks from Beach, 0.5 miles to Beach, 100 ft from bay.
The Schultz Estate
Outdoor dining
The Schultz Estate
9.6 out of 10, Exceptional, 5 reviews
"This house is great for large groups with plenty of comfortable bedrooms, three bathrooms (note one is only a tub, no shower), and loads of outdoor seating and fire options. This is an old farmhouse, so quirks of an old wooden house on the Eastern shore come with that. Personal bug spray at this property is essential as the mosquitos are very intense. The owner did stop by to give us a lawn spray for them but we did not use it as I am a master naturalist and community garden manager who is...
The Schultz Estate
Waterfront House with Dock, Kayaks, & Sailboat!
View from property
Waterfront House with Dock, Kayaks, & Sailboat!
9.4 out of 10, Exceptional, 23 reviews
"The house was nice and the property is spacious. Great views from the dining room table. A little steep heading down to the dock but not terrible. Very private setting, but also only 5 mins away from pretty much anything you could need. Some nice restaurants just across the bridge in Solomons Island. Would love to return in warmer weather to take advantage of the kayaks and water."
Waterfront House with Dock, Kayaks, & Sailboat!
The Hidaway on the Patuxent River<br>Children allowed and welcomed to stay.
3 bedrooms, iron/ironing board, WiFi, bed sheets
The Hidaway on the Patuxent River<br>Children allowed and welcomed to stay.
9.2 out of 10, Wonderful, 9 reviews
"Got to go fishing, kayaking, and swimming in the pool. Had a great time, views are wonderful and it’s a peaceful environment. 10/10 would stay again."
The price is $199
$480 total
includes taxes & fees
Jul 2 - Jul 3
The Hidaway on the Patuxent River<br>Children allowed and welcomed to stay.
Spacious River Front Home - 90 minutes from DC with Dock, Kayaks & Paddleboards
Fridge, microwave, oven, stovetop
Spacious River Front Home - 90 minutes from DC with Dock, Kayaks & Paddleboards
9.8 out of 10, Exceptional, 15 reviews
"We booked a long weekend for our daughter’s graduation from St Mary’s. The house was beautiful and so spacious for our adult children and grandchildren to all be in one location without feeling cramped. We loved having the fire pit and room to throw a football around. Thank you for sharing your home Victoria!"
Spacious River Front Home - 90 minutes from DC with Dock, Kayaks & Paddleboards
Waterfront, hot tub, screen porch, kayaks, SUP, pier fishing, private feel
Outdoor spa tub
Waterfront, hot tub, screen porch, kayaks, SUP, pier fishing, private feel
10.0 out of 10, Exceptional, 15 reviews
"The house is out there in the middle of nowhere. But it was exactly what my family needed. Perfect views everywhere you look. Lots of Wildlife. House is smaller but has everything you need from kayaks to a hot tub. Front porch overlooking bay was really nice. Beds were super comfy. Not much to complain about."
Waterfront, hot tub, screen porch, kayaks, SUP, pier fishing, private feel
Large RENOVATED 6 bedroom 5 bath private home with LOTS of space!
Fridge, microwave, oven, stovetop
Large RENOVATED 6 bedroom 5 bath private home with LOTS of space!
9.6 out of 10, Exceptional, 24 reviews
"If you have a big group this is the place for you! We had a great time!!"
Large RENOVATED 6 bedroom 5 bath private home with LOTS of space!
Shewell’s Rambler in the Chesapeake Ranch Estates
View from property
Shewell’s Rambler in the Chesapeake Ranch Estates
9.2 out of 10, Wonderful, 19 reviews
"Nice and super clean. Nice location. We will stay again next time we visit family. "
Shewell’s Rambler in the Chesapeake Ranch Estates
Riverside House w/ Kayaks, Piano & Fireplace
Fridge, microwave, stovetop, dishwasher
Riverside House w/ Kayaks, Piano & Fireplace
8.8 out of 10, Excellent, 10 reviews
"Clean property and just what we needed to gather with family nearby"
Riverside House w/ Kayaks, Piano & Fireplace
'JuJu's Place' Warsaw House w/ Deck & Tree Swings!
Property grounds
'JuJu's Place' Warsaw House w/ Deck & Tree Swings!
10.0 out of 10, Exceptional, 30 reviews
"The house was beautiful and so comfortable. Everything was wonderful"
'JuJu's Place' Warsaw House w/ Deck & Tree Swings!
2 blocks from Bay! Private beach! Boat launch! Kayak! Hike! No cleaning fee!
Beach
2 blocks from Bay! Private beach! Boat launch! Kayak! Hike! No cleaning fee!
2 blocks from Bay! Private beach! Boat launch! Kayak! Hike! No cleaning fee!
Private Getaway at Four Waters Estate!
Interior
Private Getaway at Four Waters Estate!
Private Getaway at Four Waters Estate!
Tiki Time at River Point Cottage - Steps to the Beach, Dog Friendly
Exterior
Tiki Time at River Point Cottage - Steps to the Beach, Dog Friendly
Tiki Time at River Point Cottage - Steps to the Beach, Dog Friendly
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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

Blue Heron Cottage is cozy & convenient. Renovated March 2023!
Property grounds
Blue Heron Cottage is cozy & convenient. Renovated March 2023!
10.0 out of 10, Exceptional, 22 reviews
"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!
Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing
Property grounds
Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing
9.8 out of 10, Exceptional, 107 reviews
"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 $185
$285 total
includes taxes & fees
Jun 17 - Jun 18
Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing
Peaceful Water Front Cabin on Winery Grounds
TV, fireplace, DVD player, books
Peaceful Water Front Cabin on Winery Grounds
9.8 out of 10, Exceptional, 23 reviews
"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 $119
$269 total
includes taxes & fees
Jul 9 - Jul 10
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 Vacation Homes information

Number of reviews
329
Accommodation
207 Vacation Homes
Lowest Price
$199
Highest Price
$199

Recent reviews of Leonardtown hotels
Expedia verified reviews

Red Roof Inn Dahlgren - Naval Base

Red Roof Inn Dahlgren - Naval Base

5/5 Excellent
"Lady at the front desk is polite room is clean, I used the Gym, it was also clean, good budget hotel. "
A verified traveler stayed at Red Roof Inn Dahlgren - Naval Base
Posted 1 day ago
Red Roof Inn Dahlgren - Naval Base