Search Cottages in St. Leonard

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Compare 63 Cottages in St. Leonard with updated reviews, rates, and availability.

Soul Oasis - home on the Chesapeake Bay
Exterior
Soul Oasis - home on the Chesapeake Bay
9.8 out of 10, Exceptional, (16)
"Great little spot to enjoy the coast and Calvert Cliffs area. Close enough to shopping and restaurants but still secluded in nature. Teresa was great with answering questions timely and had the place looking good when we got there."
The price is SAR 488
SAR 1,087 total
includes taxes & fees
12 Nov - 13 Nov
Soul Oasis - home on the Chesapeake Bay
Waterfront Cottage in Beautiful Hoopers Island
Enjoy a beautiful sunrise from the back deck
Waterfront Cottage in Beautiful Hoopers Island
10.0 out of 10, Exceptional, (62)
"Very comfortable get-a-way for 2. Spectacular view! Good restaurants nearby."
Waterfront Cottage in Beautiful Hoopers Island
"Point of View" Waterfront cottage with panoramic views on Tilghman Island
Blue heron sunset
"Point of View" Waterfront cottage with panoramic views on Tilghman Island
10.0 out of 10, Exceptional, (7)
"“Point of View” waterfront cottage did not disappoint. In fact, it was beyond expectations. Maria’s (the host) personal touches made the cottage feel like home. We used “Point of View” as overflow for a family reunion we were having. It is perfectly situated for easy walking to anything you need or want to do on Tilghman Island. The views from the cottage are amazing. Being on the entrance to Dogwood Harbor provides you with a real time experience of what a waterman’s life is truly all...
"Point of View" Waterfront cottage with panoramic views on Tilghman Island
Cozy Virginia Potomac Riverfront Cottage
Watching sunrise
Cozy Virginia Potomac Riverfront Cottage
9.8 out of 10, Exceptional, (34)
"This is a nice little cottage, tucked away from everything right on the river. I was looking for some peace and quiet, and that’s exactly what I got. Even though the weather wasn’t great, the sunroom still let me enjoy the views. "
Cozy Virginia Potomac Riverfront Cottage
Piney Point, private , Beach Front Cottage
Beach
Piney Point, private , Beach Front Cottage
10.0 out of 10, Exceptional, (86)
"This house is beautiful and has everything anyone could ask for. The scenery is spectacular too. We enjoyed sitting outside watching the sun set, just listening to the water and enjoying a fire on the beach. The kitchen is any cook's dream! The owners are wonderful and communicated with us wonderfully. We would give it a 10 rating if possible and will certainly be back. One of our best vacations!"
Piney Point, private , Beach Front Cottage
Waterfront property with private boat ramp and new dock!
Exterior
Waterfront property with private boat ramp and new dock!
9.6 out of 10, Exceptional, (8)
"Thoroughly enjoyed our stay! Cottage was comfortable and very clean with everything we could have needed! "
Waterfront property with private boat ramp and new dock!
North Beach Cottage - Walk to Chesapeake Bay
North Beach Vacation Rental | 3BR | 2BA | 1,304 Sq Ft | Steps Required to Access
North Beach Cottage - Walk to Chesapeake Bay
10.0 out of 10, Exceptional, (27)
"This little farmhouse is great. Updated and very clean with an unbelievable location just a short walk to the beach. "
North Beach Cottage - Walk to Chesapeake Bay
Block to Beach! Fossil Hunting, Hot Tub, Coffee Bar, Screened Deck, 1hr to DC
Outdoor dining
Block to Beach! Fossil Hunting, Hot Tub, Coffee Bar, Screened Deck, 1hr to DC
10.0 out of 10, Exceptional, (12)
"What a wonderful bungalow! Convenient location for Calvert Cliffs hiking, Cove Point lighthouse, PAX Naval Air Museum and Calvert Marine Museum. We really enjoyed the screened porch for relaxing and our meals. Special treat with the coffee bar. Kitchen was stocked with everything we needed. "
Block to Beach! Fossil Hunting, Hot Tub, Coffee Bar, Screened Deck, 1hr to DC
Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing
Property grounds
Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing
9.8 out of 10, Exceptional, (123)
"We chose to celebrate our 10th wedding anniversary here for a quiet weekend away with our dog. The house provided everything we needed and the owners were great to deal with. Highly recommend!! "
Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing
Updated North Beach Cottage: Pet Friendly!
North Beach Vacation Rental | 3BR | 2BA | 1,440 Sq Ft | Stairs Required to Enter
Updated North Beach Cottage: Pet Friendly!
10.0 out of 10, Exceptional, (11)
"We came into town over the weekend for a family funeral. The house was perfect. So cute and clean. Location is great. House has everything you need and comfy beds. Would definitely stay here again."
Updated North Beach Cottage: Pet Friendly!
Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.
Living area
Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.
10.0 out of 10, Exceptional, (40)
"Nice place to stay for work trip. "
The price is SAR 526
SAR 1,087 total
includes taxes & fees
5 Dec - 6 Dec
Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.
Off-season prices! Waterfront Cottage on Hoopers Island. Pet friendly. 🏝️🦀🎣
Every sunrise brings new hope for a brighter future.
Off-season prices! Waterfront Cottage on Hoopers Island. Pet friendly. 🏝️🦀🎣
10.0 out of 10, Exceptional, (46)
"Great experience, wonderful cozy cottage with thoughtful touches throughout. Remote, peaceful location with excellent fishing and crabbing all around you. Fantastic eating at Old Salty's less than a couple of miles away. Very dog friendly cottage and lovely screened in porch area to sit and watch the sunsets. We will be booking again next year."
Off-season prices! Waterfront Cottage on Hoopers Island. Pet friendly. 🏝️🦀🎣
Waterfront Cottage in Piney Point w/ Kayaks!
Piney Point Vacation Rental | 3BR | 1.5BA | 2,484 Sq Ft | Stairs Required
Waterfront Cottage in Piney Point w/ Kayaks!
7.6 out of 10, Good, (4)
"First, this was a last minute booking, due to our inability to stay at our original rental. Becky was responsive to our needs so we could vacate our previous rental without delay. Next, what I loved about this property, and something you do not get very often is the amount of living, relaxing space there is in this rental. Several areas for groups of people to spread out, watch TV, look at the water, play games, often times while there are several bedrooms, there are precious few places for...
Waterfront Cottage in Piney Point w/ Kayaks!
Scenic Sunsets star lite sky between Pax River and Wash DC. Experiences Await!
Lovely colorful sunsets!
Scenic Sunsets star lite sky between Pax River and Wash DC. Experiences Await!
10.0 out of 10, Exceptional, (4)
"What a wonderful quick getaway weekend from DC! The quiet neighborhood, front row river views, and wonderful hospitality was unmatched! What a great way to get to know St Mary’s County!"
Scenic Sunsets star lite sky between Pax River and Wash DC. Experiences Await!
Cozy Cottage with access to and partially obstructed views of the bay.
Exterior
Cozy Cottage with access to and partially obstructed views of the bay.
9.4 out of 10, Exceptional, (13)
"Away from the hustle and bustle of any city but close enough to get anything you need. Our stay was very relaxing and Hyrum and Lisa were the best hosts we have had so far... Will definitely look for them again if we are in the area again..."
Cozy Cottage with access to and partially obstructed views of the bay.
2 Bedroom Cozy Beach Cottage with Beach Access
Exterior
2 Bedroom Cozy Beach Cottage with Beach Access
10.0 out of 10, Exceptional, (10)
"This was the perfect cottage for our family's fall getaway to St. Mary's! The host was wonderfully communicative and the cottage was perfectly appointed for our little get away. We will definitely be back!"
2 Bedroom Cozy Beach Cottage with Beach Access
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
Exterior
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
10.0 out of 10, Exceptional, (2)
"This was an amazing property. Very clean and very cute and cozy. Beautiful property. The owners were fantastic. Very responsive and caring. Loved it! Would definitely return."
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
WATERFRONT GETAWAY- Charming Waterfront Cottage on St Clements Bay
Kayak view
WATERFRONT GETAWAY- Charming Waterfront Cottage on St Clements Bay
10.0 out of 10, Exceptional, (62)
"We had a great time, cottage adorable and updated."
WATERFRONT GETAWAY- Charming Waterfront Cottage on St Clements Bay
Cottage Located on the Patuxent River!
Room
Cottage Located on the Patuxent River!
10.0 out of 10, Exceptional, (38)
"The property and the cottage are just beautiful [very quiet] and incredibly well appointed. The bed is super cozy. There is no kitchen but the coffee station was great to have. Note that the cottage shares the property with the main house. My husband and I enjoyed sitting by the river multiple times during our stay and we really appreciated our hosts’ hospitality and communication. Thank you for the beautiful respite!"
The price is SAR 1,221
SAR 1,473 total
includes taxes & fees
10 Nov - 11 Nov
Cottage Located on the Patuxent River!
Family-friendly Chesapeake Beach House With Deck!
Living area
Family-friendly Chesapeake Beach House With Deck!
3.0 star property
6.0 out of 10, (1)
Family-friendly Chesapeake Beach House With Deck!
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

Discover tranquility near Calvert Cliffs
Property grounds
Discover tranquility near Calvert Cliffs
9.8 out of 10, Exceptional, (15)
"Peaceful, relaxing, lots of nature with a beautiful home to accompany the experience. We had everything we needed and hated to leave!"
Discover tranquility near Calvert Cliffs
Mid-Century Modern and Marvelous on the Bay
Property grounds
Mid-Century Modern and Marvelous on the Bay
10.0 out of 10, Exceptional, (69)
"Hands down our favorite place to stay! Would love to keep in a secret, but need to sing its praises. Nick is awesome and answers any questions you may have. The house is well appointed, lovely neighborhood and location is perfect to rest and relax. "
Mid-Century Modern and Marvelous on the Bay
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, (17)
" 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...
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!
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.

Frequently asked questions

How much do cottages in St. Leonard cost?
Cottages in St. Leonard range between SAR 488 and SAR 1,221 per night. These retreats offer a chance to get reacquainted with nature — at a price you can afford. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
Why book your cottage in St. Leonard with Expedia?
Booking a cottage in St. Leonard is as easy as clicking on your travel dates and picking an ideal place for outdoor recreation and relaxation. From upmarket retreats to budget-friendly stays and cottages that offer amenities like a kitchenette, Expedia has something for all tastes. As for epic deals? We have them too!
How can I find cheap cottages in St. Leonard?
A good way to uncover cheap cottages in St. Leonard is with Expedia’s convenient filter tool. Narrow down your search by star rating, amenities and budget to grab awesome bargains in just a few clicks.