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Compare 171 Vacation Homes in St. Leonard with updated reviews, rates, and availability.

Beautiful Waterfront Retreat in Cambridge!
10.0 out of 10, Exceptional, (26)
"Great house and location. Very family friendly! "
The price is SAR 1,032
SAR 1,933 total
includes taxes & fees
26 Sep - 27 Sep
Beautiful Waterfront Retreat in Cambridge!
Blocks to the Boardwalk!
9.8 out of 10, Exceptional, (31)
"We had fun"
Blocks to the Boardwalk!
Waterfront Paradise with Pool & Hot Tub plus 4 King Beds & 4 Full baths
10.0 out of 10, Exceptional, (71)
"We had an incredible stay at this beautiful VRBO home! The property itself is nothing short of stunning, with a magnificent view of the river that we enjoyed every morning. The pool was fabulous, perfect for relaxing and having fun with our family. The house was extremely comfortable, spotlessly clean, and fully equipped with everything we needed for a perfect vacation. Every detail was thoughtfully considered, making it feel like a true home away from home. There were plenty of fun and...
Waterfront Paradise with Pool & Hot Tub plus 4 King Beds & 4 Full baths
Secluded Luxury waterfront cottage with private deep water pier!
10.0 out of 10, Exceptional, (69)
"The house was in tip top shape. The property had great views and all the amenities you could want. We used the fire pit every evening, as well as the crab trap and swimming off the dock"
Secluded Luxury waterfront cottage with private deep water pier!
The Normandy Cottage ~ Charming Getaway ~ On The Shores Of The Chesapeake!
9.6 out of 10, Exceptional, (39)
"I was very impressed with this property. It's a cute little house that was comfortable for our group of 6. It was at a great location, too. The owner was quick to respond to my questions. If we visit North Beach again, I will definitely book here again."
The Normandy Cottage ~ Charming Getaway ~ On The Shores Of The Chesapeake!
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)
"Really nice home, beautiful view and communication was great. I would happily stay there again in the future. "
The price is SAR 694
SAR 1,578 total
includes taxes & fees
24 Sep - 25 Sep
Waterfront Relaxing Getaway
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!
9.6 out of 10, Exceptional, (14)
"Amazing time with friends and family at this property. I just need to remember to buy more bug spray haha. Regardless though- it was worth it"
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock
9.8 out of 10, Exceptional, (70)
"We enjoyed our stay a great deal. Jon is a great host, the house was comfortable and spacious, and the view of the night sky from the pier was spectacular."
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock
Belle of the Chesapeake Bay
9.8 out of 10, Exceptional, (7)
"We enjoyed our stay at the Belle of the Chesapeake. The house was very spacious and had a cozy feel. We had a concern & was extremely pleased at how quickly Becky responded to our text and took care of the situation. We look for many things in homes but always appreciate when we get the personal touch. We loved the closeness to Solomon’s Island & Driftwood Beach. I would definitely recommend this house. Thanks , Wanda"
Belle of the Chesapeake Bay
Waterfront Getaway with Dock
10.0 out of 10, Exceptional, (34)
"A perfect escape from city living! Clean property, easy to access kayaks and canoe for wonderful paddling right from the dock and a great fire pit in the yard. So peaceful. The bathrooms were clean and inviting after a day on the water. The kitchen had everything needed to help enjoy a cooked meal of fresh veggies from nearby Emily’s Produce (BIG recommendation!). Thank you"
The price is SAR 863
SAR 1,046 total
includes taxes & fees
15 Oct - 16 Oct
Waterfront Getaway with Dock
BeachWalk Cottage - Charm by the Chesapeake Bay
9.8 out of 10, Exceptional, (81)
"This beach cottage was just what our family, pup included, needed for a long weekend getaway! The furnishings were nice and comfortable. We discovered the beach toys on the second day and my son loved being able to build a sand castle. There were a few minor things that would have made the stay even better: the back sliding door was very difficult to open/close and there was no soap for the dishwasher."
BeachWalk Cottage - Charm by the Chesapeake Bay
Stylish & Modern Waterfront retreat, Serene and with great views,1Hr to DC
10.0 out of 10, Exceptional, (9)
"This was an amazing property. The water views are stunning, and the owners thought of everything from make-up wipes to tea bags to an over-abundance of extra towels and even filled ice cube trays in the freezer. Nothing has been missed to offer guests everything they need! The beds were very comfortable, the shower was spa-like, and overall space was impeccably kept up and clean. The owners are generous and great with communication! We will definitely be back!"
Stylish & Modern Waterfront retreat, Serene and with great views,1Hr to DC
Waterfront home with private dock
10.0 out of 10, Exceptional, (6)
"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."
Waterfront home with private dock
WATERFRONT!!! The River's Roost on The Patuxent River
10.0 out of 10, Exceptional, (15)
"Great place with lots of room. Very relaxing and a great host"
WATERFRONT!!! The River's Roost on The Patuxent River
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
Waterfront Home, Large Property with Pool, Discount for Monthly/Seasonal Rentals
9.6 out of 10, Exceptional, (19)
"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!!!"
Waterfront Home, Large Property with Pool, Discount for Monthly/Seasonal Rentals
Blue Heron Retreat on the Water
10.0 out of 10, Exceptional, (9)
"We had a relaxing stay at the Blue Heron Retreat. The house is as described. The beds were very comfortable and it was nice sitting out on the decks having our morning coffee and listening to the birds. We used the hot tub every day since it’s shaded by trees so even though we had hot weather, we were still able to use it during the day. "
Blue Heron Retreat on the Water
New Rates! Experience the Chesapeake Bay lifestyle at the historic and waterfront Bay Dreams
3.0 star property
10.0 out of 10, Exceptional, (1)
New Rates! Experience the Chesapeake Bay lifestyle at the historic and waterfront Bay Dreams
Fish, kayak, bike, and more at this private serene 24-acre waterfront estate.
2.0 star property
10.0 out of 10, Exceptional, (3)
"Photos are accurate and it was great to have a dock to go out on. It was very peaceful. Unfortunately, we didn’t catch any fish or crabs in late August. House has a comfortable layout. Lots of outdoor games for kids. Communication with the host was easy and timely. Close to Cambridge lighthouse, RAR brewery, and blackwater nature reserve. NOTE: If you plan on cooking with your group, I’d recommend bringing some basics, knives and serving bowls. The kitchen did have good pans, pots and lids. "
Fish, kayak, bike, and more at this private serene 24-acre waterfront estate.
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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 St. Leonard

Welcome to Hickory House on the Chesapeake Bay!
9.6 out of 10, Exceptional, (21)
"The house was perfect for a quiet getaway to relax in. Parking pass available was a bonus since the bay is walking distance. Finding a place to include our puppy made the whole experience worth while."
Welcome to Hickory House on the Chesapeake Bay!
Waterfront house with private beach and pier
9.8 out of 10, Exceptional, (14)
"Peaceful, relaxing, lots of nature with a beautiful home to accompany the experience. We had everything we needed and hated to leave!"
Waterfront house with private beach and pier
El Camino
10.0 out of 10, Exceptional, (29)
"100% recommend"
El Camino
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.