Search Vacation Homes in St. Leonard

Plan, book, stay with confidence

Be picky

Search almost a million properties worldwide

Treat yourself

Change your mind

Book hotels with free cancellation

Compare 175 Vacation Homes in St. Leonard with updated reviews, rates, and availability.

"This home was perfect for our 12-person family. There was plenty of room to spread out, and the house was well stocked with everything we needed. It would be a great place to vacation in the summer as well. The owner was helpful, communicated well, and accommodating. We hope we can return sometime in the future."

The driveway allows for plenty of parking for guests!

"This was our third year celebrating our family Thanksgiving in this home. Three generations coming from three different states. Location offers an easy drive for everyone, and the home is large enough for us spread out yet gather for meals. The host listened to our comments from previous years and addressed all of our concerns. Will be returning again."

"My family of five and our pup just had a wonderful Thanksgiving break staying at the lazy crab. The home was very clean, equipped with just the right amount of things to make our stay easy without cluttering the space. The beds were comfortable, the fenced in yard was perfect for our four-legged family member, and we enjoyed being able to walk to restaurants and to the beach. Everyone we encountered was kind and welcoming in town, and we had fun digging for shark teeth with our kids too. Even in...

"We stayed here for four days over July 4th holiday. The house is clean, modern, updated and looked new on the inside. Well equipped with linens, towels, bath products, appliances and accessories. Conveniently located to Herrington Harbor marina for events and weddings. Huge fenced backyard which was great for kids and pets to run around. There were a couple of minor issues with the AC (due to a storm power outage) and the guests before us also didn’t take out their trash so the can was full. But...

"Everything close by!"

"Nice house, beautiful waterfront property, great host. No complaints whatsoever, highly recommend. "

Cambridge Vacation Rental | 7BR | 5.5BA | Stairs Required | 10,333 Sq Ft

" October 11-14, 2024, we rented the “Willoughby” for a family reunion. Let me start out by saying this home is amazing. It looks exactly as pictured based on the website photos. It was even better than I expected. If you are considering this property, I highly recommend booking it! Believe me when I say the Willoughby is a rare gem. The location of the home is perfect and extremely private. The grounds are pristine and the view of the water is breathtaking. The home sits on the Hudson...

Sunroom off the kitchen and living room with a magnificent view of the Chesapeake Bay

"Very nice place we found, great views, very clean, quiet, great place to relax for the weekend. everything went well and we would highly recommend anyone for a stay here. we will be back next year"

"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."

"House is perfect for families to get together for a holiday. Has pretty much everything you need."

WELCOME FRIENDS TO—
“THE NORMANDY COTTAGE

"We stayed for the weekend to attend a wedding nearby. The size of the home was perfect for our family of 5. It was clean and well equipped. We enjoyed morning coffee on the deck! The only issue was that one of the queen beds was really hard and not very comfortable. "

Sit on the patio and enjoy your coffee in the morning.

"The house was very comfortable and well stocked! It has everything you need for a relaxing time. "

living room, there is TV with netflix/ prime streaming.

"Great place to stay while in the area. Thank you!"

"Classic cottage, very clean and well-supplied. Comfy bed in main bedroom! Beautiful property on the river - quiet and peaceful. Lovely sitting areas both inside and out. Restorative!"

"We stayed here over the Labor Day weekend to celebrate a 40th birthday with friends and family. We had an amazing time and the weather was perfect. We enjoyed using the dock for swimming, crabbing and fishing during the day and enjoyed grilling and fires at night. The kids loved the kayaks, air hockey table and bunkbeds. And the views of the water from the house and patio were excellent! We highly recommend staying here and we will definitely return."

Ariel view of the house, dock and beautiful Chesapeake Bay.

"The place was perfect for our group of friends (4 couples) Everyone had a King Bed, and their own bathroom, We rent our home in NJ so really appreciate how well the house was appointed. It had everything we needed. My only suggestion is a repeater so the internet connectivity is less spotty than we experienced. The TV's kept buffering in the bedrooms. "

"The house was just as it was listed!! Our annual family vacation was so much fun here! Plenty of room, very clean, and fully stocked! Peddle boats, kayaks, and pool used daily!! Fire every night!!! Thank you for the wonderful hospitality!!!"

Lusby Vacation Rental | 4BR | 3BA | 3,720 Sq Ft | Stairs Required

"Our family was looking for a place to gather to visit our Aunt who lives in the area. Six of us stayed at the Waterfront Lusby home and hosted a dinner for our Aunt and cousins. There was plenty of space for our gathering in addition to the comfortable accommodations for our weekend stay. The neighbors were very friendly and welcoming."

"We were in the area to visit our grand daughter who was graduating from the University of Maryland. It was great to find a nice homey property so close to get house in Mechanicsville. "

"We were in town for a reunion and this was a nice alternative to the local hotels. Updates to the house were nicely done and I love that checkout was simplified to two to three tasks, not a whole laundry list. If I had two suggestions, one would be that the plug-ins were too many and too strong - we considered opening a window for some relief but did not since we were out at the reunion most of the day. But only one per floor would likely be enough although the house is so clean (five stars!)...