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Check prices for these dates

Next weekend
28 Mar - 30 Mar
In two weeks
4 Apr - 6 Apr
In one month
18 Apr - 20 Apr
In two months
16 May - 18 May

Compare 263 Vacation Homes in Leonardtown with updated reviews, rates, and availability.

Sunrise Views: Waterfront Lusby Home w/ Deck!
Outdoor dining

Sunrise Views: Waterfront Lusby Home w/ Deck!

9.6 out of 10, Exceptional, (8)
"Absolutely an amazing place to get away, and enjoy the beautiful views of the Bay. Well appointed house, immaculately maintained. Short distance to town, and short distance to each hikes. "
Sunrise Views: Waterfront Lusby Home w/ Deck!
Belle of the Chesapeake Bay
Beach

Belle of the Chesapeake Bay

9.2 out of 10, Wonderful, (12)
"Our granddaughters live in the neighborhood and our youngest was having her first birthday! It was just my husband and myself, way more house than we needed but tons more comfortable than a hotel. The winter views of the Bay from the living room were awesome. I highly recommend you make a cup of coffee and watch the sunrise. A few surprises with the house itself, the most egregious for me was the fireplace pictured is not functional. The hosts have done a nice job with this house and are still...
Belle of the Chesapeake Bay
4-BR Waterfront Turret Home
Interior

4-BR Waterfront Turret Home

2.0 star property
10.0 out of 10, Exceptional, (1)
"Absolutely wonderful home with the best view of the water from nearly every window. It was clean and it had many comfortable bedrooms. Highly recommend this property!!"
The price is AED 1,102
AED 2,515 total
includes taxes & fees
26 Mar - 27 Mar
4-BR Waterfront Turret Home
Modern 3-bedroom house in Colonial Beach with access to pool and private hot tub
Interior

Modern 3-bedroom house in Colonial Beach with access to pool and private hot tub

Modern 3-bedroom house in Colonial Beach with access to pool and private hot tub
Beachy Maryland A-Frame: Steps to Chesapeake Bay!
Interior

Beachy Maryland A-Frame: Steps to Chesapeake Bay!

9.8 out of 10, Exceptional, (9)
"I loved this sweet A frame home! Celebrated my 48th birthday with a girls' trip and we all loved it. Enjoyed fires and Christmas movies each night. House has a lot of space and is so comfortable. Loved the views of the Bay, particularly from the sunroom and porch. Found quite a bit of sea glass on the neighborhood beach, as well as at the house beach during low tide. Owner was incredibly responsive and went above and beyond. Great place. Would highly recommend. "
Beachy Maryland A-Frame: Steps to Chesapeake Bay!
River Refresh - Waterfront with Spa on Placid Bay
Outdoor dining

River Refresh - Waterfront with Spa on Placid Bay

10.0 out of 10, Exceptional, (8)
"Wonderful getaway! "
The price is AED 918
AED 1,922 total
includes taxes & fees
24 Mar - 25 Mar
River Refresh - Waterfront with Spa on Placid Bay
Inviting and Serene Home on Monroe Bay Creek
Fridge, microwave, oven, stovetop

Inviting and Serene Home on Monroe Bay Creek

10.0 out of 10, Exceptional, (64)
"This is such a perfect home and property on the river with many fun things to do. And an amazing host to go along with it, who provided many small details and touches that we didn’t expect, but truly enhanced the visit. Thanks!"
Inviting and Serene Home on Monroe Bay Creek
Perfect Pointe, Cobb Island, Maryland
Miscellaneous

Perfect Pointe, Cobb Island, Maryland

10.0 out of 10, Exceptional, (52)
"Family adventure with our two adult children and their families. Perfect Pointe met all our needs and more. The house had plenty of space and comfort throughout. Outdoors provided numerous opportunities for any number of interests. Definitely plan a return! The Kling Family."
Perfect Pointe, Cobb Island, Maryland
Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp
Miscellaneous

Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp

9.8 out of 10, Exceptional, (59)
"Property was exactly as advertised. Charming Farmhouse with plenty of space situated on a large property with a private beach. We even enjoyed some of the local restaurants, Captain Pat's Seafood and Tacos Haciendas."
Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp
Waterfront Wildlife Retreat on the Patuxent River
Interior

Waterfront Wildlife Retreat on the Patuxent River

10.0 out of 10, Exceptional, (159)
"The Waterfront Retreat on the Patuxent River is better than advertised. Our whole family stayed -- everyone loved it! It was clean, comfortable, with everything needed to stay comfortably, sleep, eat, relax and use as a home base for exploring. Solomons Island and the surrounding area was filled with lots of fun things to do (restaurant's, museums, history, boating, walking, etc.). "
Waterfront Wildlife Retreat on the Patuxent River
Coastal Charm and Convenience: Luxurious 5-Bedroom Just Steps From Downtown
Fridge, microwave, oven, stovetop

Coastal Charm and Convenience: Luxurious 5-Bedroom Just Steps From Downtown

10.0 out of 10, Exceptional, (12)
"Myself, my partner, my 7 family members and our 2 pups stayed here for our annual vacation to Colonial Beach & our experience was nothing short of spectacular. The host is super fast at replying, made our check in process easy, and was super hospitable. They even accommodated our last minute wish to check in early! The ONLY thing I can think of that can be improved is the level of cleanliness. Everything was beautiful and clean except for areas underneath the rugs, which were covered with sand...
Coastal Charm and Convenience: Luxurious 5-Bedroom Just Steps From Downtown
Riverfront Paradise w/ Hot Tub & Pool in Kinsale!
Outdoor spa tub

Riverfront Paradise w/ Hot Tub & Pool in Kinsale!

9.6 out of 10, Exceptional, (15)
"There are so many wonderful things to say about this beautifully maintained property. The positives were 2 dishwashers, 2 ovens, 2 refrigerators (one by the pool), ice machine, lots of seating on outside porches, large pier w/motorized lift platform to get in and out of the water, luckily a backup generator (we had a bad storm while we were there), pool is shallow and great for water walking, beautiful views from the inside and outside, great crab traps, very safe fire pit, most well equipped...
Riverfront Paradise w/ Hot Tub & Pool in Kinsale!
Large Luxury 4 bed/3 bath Beach House-2 Blocks to beach, 1 Block to Bay
Fridge, microwave, oven, stovetop

Large Luxury 4 bed/3 bath Beach House-2 Blocks to beach, 1 Block to Bay

10.0 out of 10, Exceptional, (43)
"Great time! First time in Colonial Beach. Low key family time. House was perfect location for us. Very enjoyable!"
Large Luxury 4 bed/3 bath Beach House-2 Blocks to beach, 1 Block to Bay
Beach Cottage With A Spectacular View ~ Your Own Private Beach ~ Includes Kayaks
On the beach

Beach Cottage With A Spectacular View ~ Your Own Private Beach ~ Includes Kayaks

10.0 out of 10, Exceptional, (69)
"Property provides relaxation and entertainment for all ages. If you can think of it, it's already there. Clean, well-kept everything in working order. Will definitely consider a longer stay in the future. Thank you for this opportunity. "
Beach Cottage With A Spectacular View ~ Your Own Private Beach ~ Includes Kayaks
2 Acre Oasis with Private Beach! Family and dog friendly!
Property grounds

2 Acre Oasis with Private Beach! Family and dog friendly!

10.0 out of 10, Exceptional, (48)
"We had a wonderful time at this beautiful property. We are a group of friends who have traveled from NJ and NC to meet in the middle each New Year's Eve. This was our 10th property and many in the group ranked it their favorite place we've stayed and would like to break our no return rule to come back again. The house is large and clean with a wonderful kitchen but the showstopper is being able to explore the beaches and get out into nature. Even in winter we spent most days completely outside....
2 Acre Oasis with Private Beach! Family and dog friendly!
New Island Home on the Chesapeake Bay Sunsets
Property grounds

New Island Home on the Chesapeake Bay Sunsets

10.0 out of 10, Exceptional, (5)
"A well stocked and well kept house on the water with fantastic sunset views, a big yard for games, and a game room and fire pit for the night. "
New Island Home on the Chesapeake Bay Sunsets
1 Mi to Colonial Beach Boardwalk: Home w/ Fire Pit
Miscellaneous

1 Mi to Colonial Beach Boardwalk: Home w/ Fire Pit

1 Mi to Colonial Beach Boardwalk: Home w/ Fire Pit
House Right on the Potomac River - Great Sunrises & Sunsets
Exterior

House Right on the Potomac River - Great Sunrises & Sunsets

10.0 out of 10, Exceptional, (89)
"This place is amazing for a large family getaway! Pet friendly and kid friendly. There isn’t too much around the area, but having access to a pool, the boats and canoes, fishing/crabbing supplies, and the large living area made this perfect for our trip. Multiple rooms, multiple couches and multiple areas to play board games. Definitely worth a second trip and the owner (Tom) made everything incredibly easy Thank you again for letting us use your lovely home! "
House Right on the Potomac River - Great Sunrises & Sunsets
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, (30)
"Would definitely stay again"
Waterfront with spectacular view, close to restaurants and bars
5 bedroom, 8 bed, 3 story house a block from beach
Beach

5 bedroom, 8 bed, 3 story house a block from beach

9.6 out of 10, Exceptional, (13)
"Everything went extremely smooth. Check in was easy. House was nice and clean. Had a lot of fun with the gaming stuff they had set up! The house had everything you could imagine and more! Owners were extremely nice and informative. Recommended good places to go and eat. Overall great experience and would definitely go again."
5 bedroom, 8 bed, 3 story house a block from beach
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

2 Acre Oasis with Private Beach! Family and dog friendly!
Property grounds

2 Acre Oasis with Private Beach! Family and dog friendly!

10.0 out of 10, Exceptional, (48)
"We had a wonderful time at this beautiful property. We are a group of friends who have traveled from NJ and NC to meet in the middle each New Year's Eve. This was our 10th property and many in the group ranked it their favorite place we've stayed and would like to break our no return rule to come back again. The house is large and clean with a wonderful kitchen but the showstopper is being able to explore the beaches and get out into nature. Even in winter we spent most days completely outside....
2 Acre Oasis with Private Beach! Family and dog friendly!
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, (128)
"Great little weekend getaway very quiet and enjoyed the relaxation . Very cute and clean cottage on the water "
The price is AED 643
AED 1,110 total
includes taxes & fees
31 Mar - 1 Apr
Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing
Soul Oasis - home on the Chesapeake Bay
Sun loungers, beach towels

Soul Oasis - home on the Chesapeake Bay

9.8 out of 10, Exceptional, (20)
"."
The price is AED 511
AED 1,090 total
includes taxes & fees
24 Mar - 25 Mar
Soul Oasis - home on the Chesapeake Bay
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.