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Compare 209 Vacation Homes in Leonardtown with updated reviews, rates, and availability.

Discover the charm of Colonial Beach
10.0 out of 10, Exceptional, (3)
"I was in the area for one night for business and had my young granddaughter with me. The room was very comfortable and well furnished. Lots of apps available on the TV. Location is close to plenty of restaurants and the beach. The continental breakfast was very nicely set and had lots of variety. I plan on coming back NOT for business just so I can enjoy another stay. Highly recommend."
The price is AED 521
AED 643 total
includes taxes & fees
6 Nov - 7 Nov
Discover the charm of Colonial Beach
Historic charm with modern amenities
2.0 star property
10.0 out of 10, Exceptional, (1)
"The room we stayed in had a separate bedroom, living room and bathroom. Oversized refrigerator was handy. Will definitely stay here again."
The price is AED 602
AED 686 total
includes taxes & fees
6 Nov - 7 Nov
Historic charm with modern amenities
Inviting and Serene Home on Monroe Bay Creek
10.0 out of 10, Exceptional, (62)
"Loved the location and the house is amazing. It was super quiet and close to the action if you want to seek it out. Will be on my list of repeat visits!"
Inviting and Serene Home on Monroe Bay Creek
Peace & Tranquile waterfront home, Colonial Beach
9.6 out of 10, Exceptional, (15)
"Great location"
Peace & Tranquile waterfront home, Colonial Beach
Waterfront with spectacular view, close to restaurants and bars
10.0 out of 10, Exceptional, (29)
"Would definitely stay again"
Waterfront with spectacular view, close to restaurants and bars
WATERFRONT!!! The River's Roost on The Patuxent River
10.0 out of 10, Exceptional, (18)
"This house is absolutely fabulous! Very spacious, stocked with necessary supplies and many amenities. Beautiful property and views of the water, sunrises and sunsets. We especially liked all the wonderful decks, kitchen on the bottom level, many bathrooms, and comfortable furnishings. John and Christina were excellent host. They responded immediately to any concerns or questions. They were easy to communicate with during the check-in and check-out process. I would definitely love to...
WATERFRONT!!! The River's Roost on The Patuxent River
Colonial Beach Cottage, 7 minutes walk to beach!
9.8 out of 10, Exceptional, (21)
"Very clean and comfortable. Fenced in lot was great for letting our dog walk around off leash. Off street parking was a plus. Don't miss breakfast at Lenny's a short walk away or the model train store next door."
Colonial Beach Cottage, 7 minutes walk to beach!
Secluded waterfront house to relax or enjoy water activities from private pier
9.8 out of 10, Exceptional, (25)
"Overall very pleased. Seemed like a lot of money for the property but I guess that’s what waterfront cost. House was very clean and well equipped. Loved the mini-splits in each room. The only reason I gave “cleanliness” four stars is because the outside trash can had a bunch of trash the smelled horrible and the recycling container also had trash in it. Michelle was great and very responsive. There’s a great market on the island but very few dining options and no fine dining. Very cozy...
Secluded waterfront house to relax or enjoy water activities from private pier
Beachy Maryland A-Frame: Steps to Chesapeake Bay!
9.8 out of 10, Exceptional, (7)
"Comfortable home and a great place to get away for a chance to exhale and unwind. Host was great! Sunrises, night sky and water front makes this a wonderful relaxing getaway!"
Beachy Maryland A-Frame: Steps to Chesapeake Bay!
Riverside House w/ Kayaks, Piano & Fireplace
8.8 out of 10, Excellent, (10)
"Clean property and just what we needed to gather with family nearby"
Riverside House w/ Kayaks, Piano & Fireplace
Blue Heron Retreat on the Water
10.0 out of 10, Exceptional, (10)
"The place was as described. Great communication and check in. All professional."
Blue Heron Retreat on the Water
The Schultz Estate
9.2 out of 10, Wonderful, (13)
"What a wonderful stay we had! The house was so comfortable with plenty of space for everyone to relax and enjoy each other's company. We enjoyed the brisk mornings on the porch and the gorgeous sunsets in the evenings. Very comfortable beds and linens. The scenery and landscape in the area are breathtaking. Every turn provided another incredible view of the water. Fishing Creek is close to so many beautiful, quaint towns along the Chesapeake Bay. Highly recommend!"
The Schultz Estate
Waterfront Relaxing Getaway
9.8 out of 10, Exceptional, (18)
"Nice house, beautiful waterfront property, great host. No complaints whatsoever, highly recommend. "
Waterfront Relaxing Getaway
Bay view from Calvert Cliffs, Solomons Island & State Park nearby
10.0 out of 10, Exceptional, (38)
"Our daughter and her family live in Lexington Park so we visit the area often. The hotels close by don’t offer great options for a family of four with a teenage boy and a 9 year old girl, so we started looking for VRBO houses. So glad we found this gem! Sure, it’s a bit further away from our daughter (20 min instead of 10 min), but the extra space is well worth it. We loved the electric fire place and the wrap around deck was very nice. The house has everything you need and Sara was extremely...
Bay view from Calvert Cliffs, Solomons Island & State Park nearby
**FAMILY FRIENDLY CREEKSIDE GETAWAY - HIDEAWAY AND ENJOY THE FAMILY MOMENTS**
10.0 out of 10, Exceptional, (181)
"From the listing to the greeting. It was terrific. The view was amazing, the house was great. There were a few too many bugs, dead and alive, but some bug spray could take care of.. We're planning another visit.cisit.Ithat."
**FAMILY FRIENDLY CREEKSIDE GETAWAY - HIDEAWAY AND ENJOY THE FAMILY MOMENTS**
Waterfront Lusby Retreat w/ Deep-Water Dock & Slip
9.8 out of 10, Exceptional, (10)
"We stayed for a quick weekend during a celebration of life. We enjoyed the ample communal space. Our only complaint was the lack of dog friendly space for potty breaks and there were quite a few things with notes that were broken around the house. "
Waterfront Lusby Retreat w/ Deep-Water Dock & Slip
Stunning Water Front Home 90 minutes from DC with Deepwater Dock.Bring your boat
9.8 out of 10, Exceptional, (18)
"The property is perfect for family gatherings "
Stunning Water Front Home 90 minutes from DC with Deepwater Dock.Bring your boat
Waterfront Scotland Beach Retreat w/ Private Beach
10.0 out of 10, Exceptional, (41)
"The house is lovely and very comfortable for our group of 8 friends. We would highly recommend!"
Waterfront Scotland Beach Retreat w/ Private Beach
"High Tide Tranquility"- Beach w/ BBQ
10.0 out of 10, Exceptional, (5)
"Thank you Dawn!! She helped out after a double booking for another property. She was super accommodating to a last minute booking! The house is fantastic, it couldn’t have been more perfect for my husband and I, and a friend. It was located close to both Prince Frederick and Solomon’s Island. The beach access was great! We found a few teeth. Thank you for such a nice stay!! "
"High Tide Tranquility"- Beach w/ BBQ
Stylish & Modern Waterfront retreat, Serene and with great views,1Hr to DC
10.0 out of 10, Exceptional, (10)
"Great place to stay while in the area. Thank you!"
Stylish & Modern Waterfront retreat, Serene and with great views,1Hr to DC
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

**FAMILY FRIENDLY CREEKSIDE GETAWAY - HIDEAWAY AND ENJOY THE FAMILY MOMENTS**
10.0 out of 10, Exceptional, (181)
"From the listing to the greeting. It was terrific. The view was amazing, the house was great. There were a few too many bugs, dead and alive, but some bug spray could take care of.. We're planning another visit.cisit.Ithat."
**FAMILY FRIENDLY CREEKSIDE GETAWAY - HIDEAWAY AND ENJOY THE FAMILY MOMENTS**
Waterfront Scotland Beach Retreat w/ Private Beach
10.0 out of 10, Exceptional, (41)
"The house is lovely and very comfortable for our group of 8 friends. We would highly recommend!"
Waterfront Scotland Beach Retreat w/ Private Beach
Blue Heron Cottage is cozy & convenient. Renovated March 2023!
10.0 out of 10, Exceptional, (36)
"Perfect size house. Clean/Comfortable Use of golf cart to get around was awesome. I’m already looking at my calendar for 2025 to come back. "
Blue Heron Cottage is cozy & convenient. Renovated March 2023!
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.