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Check prices for these dates

Next weekend
4 Rab. II - 6 Rab. II
In two weeks
11 Rab. II - 13 Rab. II
In one month
25 Rab. II - 27 Rab. II
In two months
23 Jum. I - 25 Jum. I

Compare 263 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, (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
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, (31)
"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
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
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
Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier
On the beach

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

10.0 out of 10, Exceptional, (113)
"This place was a wonderful spot for our family to have a long weekend getaway. It's on a bluff right next to the ocean with a glorious view and a stairway access to the beach. The beds are comfortable, the house has lots of great spaces to relax or play games, and the beach is a wonderful space to explore, find seashells and possibly a fossil sharks tooth (we had no luck there, but we did find a whale vertebrae, so that's something!). But in any event, we highly recommend! "
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
Property grounds

Picture Perfect Waterfront in town Sleeps 6 Expansive Outdoor dining area

10.0 out of 10, Exceptional, (28)
"We had a great stay, home was just as advertised. Very clean, kitchen was well stocked, nice outside area with great views. Neighborhood was very quiet and safe. We were visited every morning and evening by a mallard couple. One evening we were visited by a couple of swans. Being off-season, dining options were a few, most restaurants had limited seating and limited menus. Dockside was our favorite, Colonial Brewing, Icehouse Brewery were good. We recommend renting a golf cart to get...
Picture Perfect Waterfront in town Sleeps 6 Expansive Outdoor dining area
Beachy Maryland A-Frame: Steps to Chesapeake Bay!
Interior

Beachy Maryland A-Frame: Steps to Chesapeake Bay!

10.0 out of 10, Exceptional, (11)
"This house was just like the listing: clean, bright, and beautiful. The beds were comfortable and the kitchen was well-appointed. Even though it rained and we couldn't use the fire pit, the bird-watching was excellent! "
Beachy Maryland A-Frame: Steps to Chesapeake Bay!
Screened Patio, Deck & Grill: Saint Inigoes Home!
Outdoor dining

Screened Patio, Deck & Grill: Saint Inigoes Home!

9.0 out of 10, Wonderful, (2)
"Sweet little place on the water. Quiet neighborhood. Quick trip to campus."
Screened Patio, Deck & Grill: Saint Inigoes Home!
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
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
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
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!
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
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 SAR 938
SAR 1,984 total
includes taxes & fees
6 Apr - 7 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, (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
Newly Renovated River Retreat w/Dock and Pool
Terrace/patio

Newly Renovated River Retreat w/Dock and Pool

10.0 out of 10, Exceptional, (7)
"Large house with indoor pool and game room. It is in a neighborhood, but it's private. Lots of space upstairs and down. About a three mile drive to Calvert Cliffs State Park. Very fun stay. Host is communicative but not intrusive. Loved it!"
Newly Renovated River Retreat w/Dock and Pool
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
Waterfront House with Dock, Kayaks, & Sailboat!
Interior

Waterfront House with Dock, Kayaks, & Sailboat!

9.0 out of 10, Wonderful, (30)
"We stayed for a motorcross race (son was racing). We didnt do much at the house. Its nestled back in a quiet point on the water. Easy commute to and from to the grocery/simple shopping stores. Starbucks right down the street for you coffee lovers. The interior decor is simple and antique."
Waterfront House with Dock, Kayaks, & Sailboat!
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
Sea Glass Beach House! Large sand beach, dock and hot tub! Pets welcome!
Property grounds

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

10.0 out of 10, Exceptional, (18)
"Beautiful views for a relaxing, refreshing girls weekend away! The house was filled with everything we needed, and they were very quick to respond to any questions. Would absolutely come back!! Highly recommend!"
Sea Glass Beach House! Large sand beach, dock and hot tub! Pets welcome!
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!
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 SAR 563
SAR 1,141 total
includes taxes & fees
15 Apr - 16 Apr
Soul Oasis - home on the Chesapeake Bay
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 SAR 657
SAR 1,133 total
includes taxes & fees
31 Mar - 1 Apr
Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing
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.