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Check prices for these dates

Next weekend
4 Apr - 6 Apr
In two weeks
11 Apr - 13 Apr
In one month
25 Apr - 27 Apr
In two months
23 May - 25 May

Compare 222 Vacation Homes in St. Leonard with updated reviews, rates, and availability.

The Blue Crab Beach House - Free beach passes
Miscellaneous

The Blue Crab Beach House - Free beach passes

10.0 out of 10, Exceptional, (51)
"The Blue Crab Beach House was perfect for my wife and I and our dog. Very comfortable with a great backyard space for our dog. We loved the location - it’s just a short walk to restaurants and the bay. Very enjoyable stay and we hope to return."
The Blue Crab Beach House - Free beach passes
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
Modern Waterfront House with Amazing views!
Fridge, microwave, oven, stovetop

Modern Waterfront House with Amazing views!

Modern Waterfront House with Amazing views!
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.
Sweet Bamboo Beach Cottage
Fridge, microwave, oven, stovetop

Sweet Bamboo Beach Cottage

9.8 out of 10, Exceptional, (70)
"Couldn’t be happier with our stay. The house was exactly as pictured. Neighborhood was quiet with a small town feel. Most of the major appliances appeared relatively new, the beds were comfortable and the house was staffed with an abundance of linens and towels. Front and back yards are completely fenced in which is perfect for those with small dogs. North Beach is only a short drive from College Park, Baltimore and Annapolis. Check in was a breeze. Would definitely consider staying there...
Sweet Bamboo Beach Cottage
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
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!
The Lazy Crab Beach House - Free beach passes
Property grounds

The Lazy Crab Beach House - Free beach passes

10.0 out of 10, Exceptional, (44)
"Great location, well-maintained and comfortable place. Kitchen is well-stocked, rooms are comfortable, and the yard is a real plus!"
The Lazy Crab Beach House - Free beach passes
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
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
Time Stands Still At the Dock.
Outdoor dining

Time Stands Still At the Dock.

10.0 out of 10, Exceptional, (2)
"What a wonderful experience! A relaxing time with an amazing view! Thank you Jennifer"
Time Stands Still At the Dock.
Cozy Cottage 3 beds 2 baths
Outdoor dining

Cozy Cottage 3 beds 2 baths

9.8 out of 10, Exceptional, (78)
"Absolutely perfect, will stay here again and again when visting family in Maryland. "
Cozy Cottage 3 beds 2 baths
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
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
Interior

The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

10.0 out of 10, Exceptional, (7)
"This house is huge and has lots of different indoor and outdoor gathering spaces so the kids and adults in our group of three families didn’t have to be on top of each other in one living space the whole time. Big firepit area and huge lawn were great, and we enjoyed the kayaks and canoe. There’s a place to buy fresh crabs, oysters, and shrimp very close by, and the house has everything you need for a crab night. The owner was incredibly responsive and kind."
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
Outdoor dining

Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

9.8 out of 10, Exceptional, (38)
"Beautiful, spacious, the highlight was the view of the bay. Definitely will be back"
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
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 St. Leonard

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
New! Cozy River Cottage with great views of the water!
Interior

New! Cozy River Cottage with great views of the water!

9.6 out of 10, Exceptional, (5)
"A very nice house with an amazing view 10/10 recommend"
New! Cozy River Cottage with great views of the water!
WATERFRONT!!! The River's Roost on The Patuxent River
Fridge, microwave, oven, stovetop

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
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.