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Check prices for these dates

Next weekend
21 Saf. - 23 Saf.
In two weeks
28 Saf. - 2 Rab. I
In one month
14 Rab. I - 16 Rab. I
In two months
11 Rab. II - 13 Rab. II

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

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

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
Screened Patio, Deck & Grill: Saint Inigoes Home!
Saint Inigoes Vacation Rental | 3BR | 2BA | 3 Steps to Enter | 1,456 Sq Ft

Screened Patio, Deck & Grill: Saint Inigoes Home!

Screened Patio, Deck & Grill: Saint Inigoes Home!
Waterfront Home, Large Property with Pool, Discount for Monthly/Seasonal Rentals
Exterior

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
Large RENOVATED 6 bedroom 5 bath private home with LOTS of space!
The driveway allows for plenty of parking for guests!

Large RENOVATED 6 bedroom 5 bath private home with LOTS of space!

9.4 out of 10, Exceptional, (30)
"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."
Large RENOVATED 6 bedroom 5 bath private home with LOTS of space!
Safe Harbor at Herring Bay - Your Chesapeake Bay adventure awaits!
Private kitchen

Safe Harbor at Herring Bay - Your Chesapeake Bay adventure awaits!

10.0 out of 10, Exceptional, (5)
"Nice location. The house had everything we needed for our stay. The host was available by phone for any questions we had. I would stay again the next time I visit North Beach"
Safe Harbor at Herring Bay - Your Chesapeake Bay adventure awaits!
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!
Cambridge Vacation Rental | 7BR | 5.5BA | Stairs Required | 10,333 Sq Ft

Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!

9.6 out of 10, Exceptional, (20)
"Terrific house, beautiful scenery, property management was very responsive and helpful. Would stay again. Thank you. "
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!
Sea Glass Beach House! Large sand beach, dock and hot tub! Pets welcome!
Sunrise on your private beach

Sea Glass Beach House! Large sand beach, dock and hot tub! Pets welcome!

10.0 out of 10, Exceptional, (17)
"Great stay, easy check-in/check-out, highly recommend"
Sea Glass Beach House! Large sand beach, dock and hot tub! Pets welcome!
The Blue Crab Beach House - Free beach passes
The Blue Crab Beach House

The Blue Crab Beach House - Free beach passes

10.0 out of 10, Exceptional, (49)
"We really enjoyed our stay at The Blue Crab Beach House. The home was very clean and well accessorized. The host was very responsive and I would definitely come stay again !"
The Blue Crab Beach House - Free beach passes
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
Aerial view

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
Waterfront Lusby Retreat w/ Deep-Water Dock & Slip
Lusby Vacation Rental | 4BR | 3BA | 1,872 Sq Ft | Stairs Required

Waterfront Lusby Retreat w/ Deep-Water Dock & Slip

9.8 out of 10, Exceptional, (11)
"Would stay again. Steps down to the water are a challenge"
Waterfront Lusby Retreat w/ Deep-Water Dock & Slip
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
4-BR Waterfront Turret Home

4-BR Waterfront Turret Home

2.0 star property
10.0 out of 10, Exceptional, (1)
"Absolutely wonderful home with the best view of the water from nearly every window. It was clean and it had many comfortable bedrooms. Highly recommend this property!!"
The price is SAR 844
SAR 2,208 total
includes taxes & fees
24 Feb - 25 Feb
4-BR Waterfront Turret Home
Spectacular Waterfront Retreat with Pier

Spectacular Waterfront Retreat with Pier

10.0 out of 10, Exceptional, (7)
"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!"
Spectacular Waterfront Retreat with Pier
Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier
Sunroom off the kitchen and living room with a magnificent view of the Chesapeake Bay

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

10.0 out of 10, Exceptional, (112)
"Location was perfect for what we needed (quiet, on the beach, great views). Family & pup will definitely be back! We wished we could have stayed longer. Owner communication was wonderful, we never needed anything but knew we could reach out if we did. Very comfortable experience throughout. "
Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier
4BDRM River front house with Private Beach in Hollywood
Property grounds

4BDRM River front house with Private Beach in Hollywood

2.0 star property
9.6 out of 10, Exceptional, (5)
"This house was just what we needed for our business associates. "
4BDRM River front house with Private Beach in Hollywood
2 blocks from Bay! Private beach! Boat launch! Kayak! Hike! Fossil Hunt!
Living area

2 blocks from Bay! Private beach! Boat launch! Kayak! Hike! Fossil Hunt!

10.0 out of 10, Exceptional, (2)
"Quite and friendly neighbors "
2 blocks from Bay! Private beach! Boat launch! Kayak! Hike! Fossil Hunt!
Bay Views & Fire Pit: Taylor’s Island Retreat
Taylors Island Vacation Rental | 3BR | 2.5BA | 2,100 Sq Ft | 1-2 Steps Required

Bay Views & Fire Pit: Taylor’s Island Retreat

10.0 out of 10, Exceptional, (11)
"The house had a beautiful view. It was well stocked. Management was very responsive. Enjoyed a nice Thanksgiving with beautiful sunsets. Very private. Loved every aspect."
Bay Views & Fire Pit: Taylor’s Island Retreat
Luxury Waterfront Retreat with in ground pool and close to town
Miscellaneous

Luxury Waterfront Retreat with in ground pool and close to town

10.0 out of 10, Exceptional, (33)
"Second stay at this amazing rental. Everything was perfect just like the first visit. Gorgeous location, very clean, and all amenities you need. Will definitely be back!"
The price is SAR 1,313
SAR 2,501 total
includes taxes & fees
16 Feb - 17 Feb
Luxury Waterfront Retreat with in ground pool and close to town
Relaxing, spacious 5BR house on the Hudson Creek in charming Cambridge
Deep pier for boating and fishing

Relaxing, spacious 5BR house on the Hudson Creek in charming Cambridge

2.0 star property
10.0 out of 10, Exceptional, (1)
The price is SAR 563
SAR 1,785 total
includes taxes & fees
17 Feb - 18 Feb
Relaxing, spacious 5BR house on the Hudson Creek in charming Cambridge
Serenity Bay-Relaxing, Spacious House-Private Pool-6 bdrms-5baths
Ariel view of the house, dock and beautiful Chesapeake Bay.

Serenity Bay-Relaxing, Spacious House-Private Pool-6 bdrms-5baths

9.0 out of 10, Wonderful, (14)
"My family enjoyed our stay over Thanksgiving. Three generations with different needs and the house accommodated us well."
Serenity Bay-Relaxing, Spacious House-Private Pool-6 bdrms-5baths
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

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

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
5 bedroom, 8 bed, 3 story house a block from beach
Exterior

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!
Exterior

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!
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.