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Check prices for these dates

Next weekend
9 Jum. I - 11 Jum. I
In two weeks
16 Jum. I - 18 Jum. I
In one month
30 Jum. I - 1 Jum. II
In two months
27 Jum. II - 29 Jum. II

Compare 266 Vacation Homes in Leonardtown with updated reviews, rates, and availability.

Waterfront Wildlife Retreat on the Patuxent River
Interior

Waterfront Wildlife Retreat on the Patuxent River

10.0 out of 10, Exceptional, (161)
"Clean and nice location. Worked perfectly for our visit to the area to spend time with our daughter, son-in-law, and two perfect grandsons. Thank you for sharing your beautiful home and location. "
Waterfront Wildlife Retreat on the Patuxent River
The Beach Retreat is a cozy beach Villa with Hottub overlooking a private beach.
Outdoor spa tub

The Beach Retreat is a cozy beach Villa with Hottub overlooking a private beach.

10.0 out of 10, Exceptional, (32)
"This was a short getaway to the river for some R & R. Very nice location with wonderful view. We enjoyed the deck by the water and the spacious family room. Perfect for our little dogs too! Hope to return at some point!"
The Beach Retreat is a cozy beach Villa with Hottub overlooking a private beach.
Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp
Terrace/patio

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

9.8 out of 10, Exceptional, (60)
"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
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)
"Enjoyed our stay! Property was lovely and ample room for all."
House Right on the Potomac River - Great Sunrises & Sunsets
Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier
Interior

Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier

10.0 out of 10, Exceptional, (113)
"Location was perfect for what we needed (quiet, on the beach, great views). Family & pup will definitely be back! We wished we could have stayed longer. Owner communication was wonderful, we never needed anything but knew we could reach out if we did. Very comfortable experience throughout. "
Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier
Picture Perfect Waterfront in town Sleeps 6 Expansive Outdoor dining area
Fridge, microwave, oven, stovetop

Picture Perfect Waterfront in town Sleeps 6 Expansive Outdoor dining area

10.0 out of 10, Exceptional, (30)
"We were there for a work trip....love the house and location and views..."
Picture Perfect Waterfront in town Sleeps 6 Expansive Outdoor dining area
Beachy Maryland A-Frame: Steps to Chesapeake Bay!
Property grounds

Beachy Maryland A-Frame: Steps to Chesapeake Bay!

10.0 out of 10, Exceptional, (12)
"The home is absolutely beautiful and Dina is a great host. My family and I have full intentions of coming back!"
Beachy Maryland A-Frame: Steps to Chesapeake Bay!
Screened Patio, Deck & Grill: Saint Inigoes Home!
Fridge, microwave, stovetop, dishwasher

Screened Patio, Deck & Grill: Saint Inigoes Home!

9.4 out of 10, Exceptional, (3)
"great location relative to smc for a campus visit"
Screened Patio, Deck & Grill: Saint Inigoes Home!
1 Mi to Colonial Beach Boardwalk: Home w/ Fire Pit
Terrace/patio

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

10.0 out of 10, Exceptional, (1)
"This was the most wonderful place I’ve ever stayed. From my brother passing away the day of my arrival to my granddaughter and family moving away to Florida the day we leave. There is not one thing absolutely one thing they can do to make it any better than they have made this stay for me. I look forward to coming here many more times."
1 Mi to Colonial Beach Boardwalk: Home w/ Fire Pit
Waterfront with spectacular view, close to restaurants and bars
Exterior

Waterfront with spectacular view, close to restaurants and bars

10.0 out of 10, Exceptional, (31)
"Would definitely stay again"
Waterfront with spectacular view, close to restaurants and bars
Belle of the Chesapeake Bay
Smart TV

Belle of the Chesapeake Bay

9.2 out of 10, Wonderful, (12)
"This was a great place to stay in a quiet neighborhood, a short drive from Calvert Cliffs State Park. Plenty of space for four adults. We could have stayed longer and would not hesitate to book again."
Belle of the Chesapeake Bay
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)
"This property is AMAZING!! The house met and exceeded every expectation. From the spaciousness, cleanliness and breathtaking river views. The screen in porch was a great place for us to just hangout. The pool area was another great space to relax. The dock with crab pots and water “toys” was great and so was the fire pit. We would definitely stay again and highly recommend!!"
Riverfront Paradise w/ Hot Tub & Pool in Kinsale!
Modern 3-bedroom house in Colonial Beach with access to pool and private hot tub
Terrace/patio

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
River Refresh - Waterfront with Spa on Placid Bay
Fridge, microwave, oven, stovetop

River Refresh - Waterfront with Spa on Placid Bay

10.0 out of 10, Exceptional, (9)
"We enjoyed the trip very much - lovely views and handy to the boardwalk area of Colonial Beach (less than 15 minutes away). Responsive host - comfy beds - everything was fantastic!"
The price is SAR 938
SAR 1,955 total
includes taxes & fees
29 Apr - 30 Apr
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, (65)
"This was a great stay. Very nice, comfortable, great layout, convenient location. I highly recommend. "
Inviting and Serene Home on Monroe Bay Creek
Perfect Pointe, Cobb Island, Maryland
Terrace/patio

Perfect Pointe, Cobb Island, Maryland

10.0 out of 10, Exceptional, (52)
"The view is gorgeous and there were many wonderful activities we greatly enjoyed. We would love to come back in the future."
Perfect Pointe, Cobb Island, Maryland
Waterfront House with Dock, Kayaks, & Sailboat!
TV, fireplace, table tennis, books

Waterfront House with Dock, Kayaks, & Sailboat!

9.0 out of 10, Wonderful, (30)
"Great location to downtown Solomons Island Center."
Waterfront House with Dock, Kayaks, & Sailboat!
5 bedroom, 8 bed, 3 story house a block from beach
Fridge, microwave, oven, stovetop

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
Sea Glass Beach House! Large sand beach, dock and hot tub! Pets welcome!
Fridge, microwave, oven, stovetop

Sea Glass Beach House! Large sand beach, dock and hot tub! Pets welcome!

10.0 out of 10, Exceptional, (20)
"Great stay, easy check-in/check-out, highly recommend"
Sea Glass Beach House! Large sand beach, dock and hot tub! Pets welcome!
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
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

The Beach Retreat is a cozy beach Villa with Hottub overlooking a private beach.
Outdoor spa tub

The Beach Retreat is a cozy beach Villa with Hottub overlooking a private beach.

10.0 out of 10, Exceptional, (32)
"This was a short getaway to the river for some R & R. Very nice location with wonderful view. We enjoyed the deck by the water and the spacious family room. Perfect for our little dogs too! Hope to return at some point!"
The Beach Retreat is a cozy beach Villa with Hottub overlooking a private beach.
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, (129)
"Lovely, quiet, clean and comfy "
Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing
Soul Oasis - home on the Chesapeake Bay
Exterior

Soul Oasis - home on the Chesapeake Bay

10.0 out of 10, Exceptional, (22)
"Perfect family get away with a great view!"
The price is SAR 454
SAR 1,034 total
includes taxes & fees
29 Apr - 30 Apr
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.