Photo by Pla Jira

Search Vacation Homes in Leonardtown

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Compare 262 Vacation Homes in Leonardtown with updated reviews, rates, and availability.

Waterfront with spectacular view, close to restaurants and bars

10.0 out of 10, Exceptional, (34)
"Would definitely stay again"
Waterfront with spectacular view, close to restaurants and bars

2 Mi to Lighthouse: Waterfront Home w/ Dock!

9.0 out of 10, Wonderful, (32)
"Great location to downtown Solomons Island Center."
2 Mi to Lighthouse: Waterfront Home w/ Dock!

Inviting and Serene Home on Monroe Bay Creek

10.0 out of 10, Exceptional, (67)
"This was a great stay. Very nice, comfortable, great layout, convenient location. I highly recommend. "
Inviting and Serene Home on Monroe Bay Creek

**FAMILY FRIENDLY CREEKSIDE GETAWAY - HIDEAWAY AND ENJOY THE FAMILY MOMENTS**

10.0 out of 10, Exceptional, (187)
"We had a very relaxing weekend celebrating my 60th birthday. Ray was such a terrific host. Everything about the property and the owner was spectacular!!"
**FAMILY FRIENDLY CREEKSIDE GETAWAY - HIDEAWAY AND ENJOY THE FAMILY MOMENTS**

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

WATERFRONT!!! The River's Roost on The Patuxent River

10.0 out of 10, Exceptional, (21)
"Great stay, beautiful spot. We will be back for sure."
WATERFRONT!!! The River's Roost on The Patuxent River

High River Bank with $1M Sunset View, 3 min to College

10.0 out of 10, Exceptional, (1)
"I recently stayed at this property and had a wonderful experience. Trey was a terrific host. The location is fantastic, offering easy access to St. Mary’s College. The water view and sunsets were amazing. The cleanliness of the property was impeccable and the host did a great job of stocking the house with everything we needed. The full kitchen with labeled drawers made cooking easy. The house was roomy and the beds were extremely comfortable. It is a great set up for families. Overall, I highly...
The price is AEDĀ 984
AEDĀ 1,784 total
includes taxes & fees
6 Jun - 7 Jun
High River Bank with $1M Sunset View, 3 min to College

Potomac Rvr Woodland Cottage, Polite Pets welcomed, Central Air, Stunning Sunset

9.8 out of 10, Exceptional, (52)
"This was our second stay to visit family nearby for our annual 4th of July gathering. The cottage is clean, cozy, and comfortable. The owners are fantastic communicators and made sure we had everything we needed. We won’t hesitate to stay again in the future."
Potomac Rvr Woodland Cottage, Polite Pets welcomed, Central Air, Stunning Sunset

Peaceful and Cozy Waterfront Home [just renovated]

Peaceful and Cozy Waterfront Home [just renovated]

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

10.0 out of 10, Exceptional, (50)
"Really nice spot, beautiful scenery. Plenty of space for two families! Fire pit was a big hit during that chilly weather. "
2 Acre Oasis with Private Beach! Family and dog friendly!

Walk to Bay: Home w/ Fenced Yard in Colonial Beach

10.0 out of 10, Exceptional, (1)
"We had a great time!!!! It's a new home---the house was stocked well (you don't need to really bring much) and the backyard was perfect for dogs. Also the beds were very comfortable. A tall fence so you didn't have to worry about the dogs. The patio was set up very nicely with a fire pit, grill, table and chairs. We loved it!!!"
Walk to Bay: Home w/ Fenced Yard in Colonial Beach

Bay view from Calvert Cliffs, Solomons Island & State Park nearby

10.0 out of 10, Exceptional, (43)
"Awesome home wnd location! Would stay again!"
Bay view from Calvert Cliffs, Solomons Island & State Park nearby

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

10.0 out of 10, Exceptional, (115)
"Clean and spacious. Great views! Loved the beach! Found a bunch of fossils. Enjoyed kayaking. Overall outstanding!"
Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier

Lottsburg's Landing - Your Waterfront Escape on Wrights Cove

10.0 out of 10, Exceptional, (2)
"Plenty of room for the whole family. Huge kitchen and dining area. Location is ideal on Wright’s Cove."
Lottsburg's Landing - Your Waterfront Escape on Wrights Cove

Waterfront 3BR/3BA Getaway: Beach, Dock, Firepit! AMAZING Sweeping VIEWS!

9.8 out of 10, Exceptional, (26)
"Amazing and perfect getaway from DC. Had such a relaxing time floating in the river, we can’t wait to come back. Wonderful vacation rental, worth it and more!"
The price is AEDĀ 883
AEDĀ 2,400 total
includes taxes & fees
3 Jun - 4 Jun
Waterfront 3BR/3BA Getaway: Beach, Dock, Firepit! AMAZING Sweeping VIEWS!

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

10.0 out of 10, Exceptional, (44)
"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

Stunning secluded Luxury waterfront cottage with private deep water pier!

10.0 out of 10, Exceptional, (75)
"Great location. Spacious and clean. Easy checking in and communicate with owner."
Stunning secluded Luxury waterfront cottage with private deep water pier!

Stunning Water Front Home with Private Dock and Beach and Sunsets

9.8 out of 10, Exceptional, (20)
"The property is perfect for family gatherings "
Stunning Water Front Home with Private Dock and Beach and Sunsets

Waterfront on Hacks Creek next to Vir-Mar Beach on the Chesapeake Bay

9.8 out of 10, Exceptional, (46)
"We had a great time at my Blue Heaven. Nicely stocked kitchen, plenty of room inside and out. The kids ages 8 to 2 loved the bikes, games and puzzles. The beach was so close. Make sure to check out the stars at night AMAZING!"
Waterfront on Hacks Creek next to Vir-Mar Beach on the Chesapeake Bay

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
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.
Save an average of 15% on thousands of hotels when you're signed in