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Featured Cottages in St. Leonard

Our top choices for St. Leonard cottages

Family and Pet-Friendly, Waterfront with Pier

10.0 out of 10, Exceptional, (255)
"It is a perfect spot to relax and enjoy the water. We will book again if we are back that way. "
Family and Pet-Friendly, Waterfront with Pier

Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE

10.0 out of 10, Exceptional, (7)
"Lovely little rustic cottage full of charm.We arrived over Thanksgiving,the off season was wonderful thank s again"
Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE

Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing

9.8 out of 10, Exceptional, (144)
"We enjoyed our stay at the waterfront cottage with yoga on the dock in the morning, afternoon kayaking and dinner at Captain Billy’s Seafood restaurant. Down time spent reading and nature watching made the for the perfect weekend."
Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing

Waterfront property with private boat ramp and new dock!

9.4 out of 10, Exceptional, (13)
"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!

"Point of View" Waterfront cottage with panoramic views on Tilghman Island

10.0 out of 10, Exceptional, (11)
"We had a wonderful stay at the Point of a View Cottage! The views are spectacular and we also enjoyed how easy it was to walk to places to eat and the local market. Recommendations for places to eat were spot on and also appreciated a message over the weekend notifying us of the local craft market held Sunday morning. Would love to come again one day! "
"Point of View" Waterfront cottage with panoramic views on Tilghman Island

Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.

9.6 out of 10, Exceptional, (4)
"Just the perfect place I needed for a personal retreat. It is quiet, peaceful and serene. I would definitely visit again. "
The price is AU$465
includes taxes & fees
3 Sept - 4 Sept
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.

Waterfront Cottage in Beautiful Hoopers Island

10.0 out of 10, Exceptional, (77)
"We had a very nice stay and enjoyed the quiet environment and the amenities of the property. Lots of great area for walking. "
Waterfront Cottage in Beautiful Hoopers Island

Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)

10.0 out of 10, Exceptional, (10)
"Perfect house for a long weekend. Clean, cozy and great communication with Maxine. Would definitely stay here again when I return to Cambridge. "
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)

Cozy Virginia Potomac Riverfront Cottage

9.6 out of 10, Exceptional, (42)
"Clean, comfortable, quiet, and what a beautiful spot on the river! Thank you 😊 "
Cozy Virginia Potomac Riverfront Cottage

Cozy Cottage with access to and partially obstructed views of the bay.

9.2 out of 10, Wonderful, (28)
"Property was cozy and clean. Owners left lights on for us knowing we had a late arrival. Would definitely stay again. "
Cozy Cottage with access to and partially obstructed views of the bay.

Quick walk to the beach! Fire pit, Corn hole, Games & More!

10.0 out of 10, Exceptional, (3)
"The house was in a perfect location. Close to the beach and restaurants. The home was very comfortable, cozy and thoughtfully decorated. We will definitely be back!"
Quick walk to the beach! Fire pit, Corn hole, Games & More!

Renovated, Waterfront, Large Private Deep Water Dock, Cowboy Pool, Fire Pit

10.0 out of 10, Exceptional, (51)
"It’s a wonderful house with everything you need. The views are amazing - perfection! "
Renovated, Waterfront, Large Private Deep Water Dock, Cowboy Pool, Fire Pit

Soul Oasis - home on the Chesapeake Bay

9.8 out of 10, Exceptional, (31)
"The A-frame cottage was clean and comfortable. I was accompanied by my son and two grandchildren (ages 12 and 14), and we really loved it. We went fishing in bay at the beach area below the cottage, and also did a lot of fossil hunting along the cliffs, which are breathtaking. Our host Teresa was extremely helpful and welcoming. We will definitely be going back!"
The price is AU$472
includes taxes & fees
23 Sept - 24 Sept
Soul Oasis - home on the Chesapeake Bay

2 Bedroom Cozy Beach Cottage with Water Access

9.6 out of 10, Exceptional, (19)
"Great place to stay"
2 Bedroom Cozy Beach Cottage with Water Access

Waterfront Sunsets, Fishing, Boating, and Crabs! Paxs River, Budds Creek MIR.

10.0 out of 10, Exceptional, (12)
"Everything we needed, relaxing visit"
Waterfront Sunsets, Fishing, Boating, and Crabs! Paxs River, Budds Creek MIR.

North Beach Cottage - Walk to Chesapeake Bay

10.0 out of 10, Exceptional, (37)
"Beautiful, charming house! The owner was wonderful! She had a lovely card waiting for us with a handwritten note. Really warm welcome! Also great location!"
North Beach Cottage - Walk to Chesapeake Bay

WATERFRONT GETAWAY- Charming Waterfront Cottage on St Clements Bay

10.0 out of 10, Exceptional, (68)
"We had a great time, cottage adorable and updated."
WATERFRONT GETAWAY- Charming Waterfront Cottage on St Clements Bay

Cedar Point 6.5 Acre Waterfront Family Retreat With Pool And Sandy Beach!

10.0 out of 10, Exceptional, (88)
"Beautiful property in a great location!"
Cedar Point 6.5 Acre Waterfront Family Retreat With Pool And Sandy Beach!

Waterfront Island Cottage with Loft and Private Pier

2.0 star property
10.0 out of 10, Exceptional, (1)
"This property was everything we hoped for and more. Impeccably clean, beautifully maintained, and the view was just breathtaking — even better than the photos. The host was incredibly responsive and helpful, which made our stay even more seamless and enjoyable. Every detail was perfect, and we loved every minute. We’ll definitely be back and highly recommend this gem!! Thanks, Allen. "
Waterfront Island Cottage with Loft and Private Pier

Perfect family/friend getaway. Kayaks and bikes provided.Walk to Herrington Harb

9.6 out of 10, Exceptional, (91)
"We had a great time at this place. Close enough to walk to town if necessary would definitely book again for a weekend getaway."
Perfect family/friend getaway. Kayaks and bikes provided.Walk to Herrington Harb
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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Top St. Leonard Hotel Reviews

Find out more about St. Leonard

Find out more about St. Leonard

St. Leonard Cottages information

Number of reviews
647
Accommodation
91 Cottages
Lowest Price
AU$465
Highest Price
AU$567

Frequently asked questions

How much do cottages in St. Leonard cost?
You can expect to pay between AU$465 and AU$567 per night for cottages in St. Leonard. No matter your budget, an ideal stay is just clicks away on Expedia. This price was 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.
What is there to do in St. Leonard near my cottage?
If you want to fill up your itinerary in St. Leonard, make your way to Running Hare Vineyard. It's a winner among tourists and locals alike.