St. Leonard Vacation Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for St. Leonard vacation homes

Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.

Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.
Prince Frederick
9.8 out of 10, Exceptional, (6 reviews)
"Our family had a great stay. Thank you!"
United States
Colleen G.
The price is CA $284
CA $593 total
includes taxes & fees
Apr 14 - Apr 15
Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.

Family Beach House: Spacious Deck, Grill & Views

Family Beach House: Spacious Deck, Grill & Views
Chesapeak beach
9.0 out of 10, Wonderful, (6 reviews)
"Everything was great. The owner was extremely helpful. Couldn't ask for anything better."
United States
Bryan P.
The price is CA $235
CA $613 total
includes taxes & fees
Apr 13 - Apr 14
Family Beach House: Spacious Deck, Grill & Views

Walk to Beach! King Bed & Free Beach Passes

Walk to Beach! King Bed & Free Beach Passes
North Beach
10.0 out of 10, Exceptional, (19 reviews)
"Delightful one-night stay! Place was clean, quiet, convenient and very comfortable. Especially grateful that our beloved dog was welcomed"
United States
Elaine D.
The price is CA $164
CA $513 total
includes taxes & fees
Apr 19 - Apr 20
Walk to Beach! King Bed & Free Beach Passes

Sunset Breezes - quiet waterfront retreat

Sunset Breezes - quiet waterfront retreat
Dorchester County
10.0 out of 10, Exceptional, (43 reviews)
"Clean, quiet, comfy"
United Kingdom
Deborah V.
The price is CA $461
CA $582 total
includes taxes & fees
May 6 - May 7
Sunset Breezes - quiet waterfront retreat

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

2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!
Prince Frederick
10.0 out of 10, Exceptional, (10 reviews)
"Such a cool neighborhood! Easy walk to an amazing private beach. Would love to stay again. "
United States
Olivia M.
The price is CA $370
CA $695 total
includes taxes & fees
Apr 15 - Apr 16
2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!

4-BR Waterfront Turret Home

4-BR Waterfront Turret Home
Solomons
10.0 out of 10, Exceptional, (7 reviews)
"Beautiful house. Beautiful scenery. Everything was perfect. "
United States
Thomas S.
The price is CA $484
CA $1,091 total
includes taxes & fees
Apr 13 - Apr 14
4-BR Waterfront Turret Home

Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
North Beach
10.0 out of 10, Exceptional, (32 reviews)
"Perfect place to spend quality time with our three adult children and their significant others. "
United States
Malarkey F.
The price is CA $219
CA $668 total
includes taxes & fees
Apr 20 - Apr 21
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

Tranquil Modern Farmhouse

Tranquil Modern Farmhouse
Waldorf
9.2 out of 10, Wonderful, (7 reviews)
"This property was super gorgeous and spacious so we were able to relax. Guests had more than enough space and didn’t feel like they were on top of each other sleeping wise! We were able to just have dinner and feel safe! The owner answered any questions we had within 15 minutes, which was super helpful! "
United States
khaddija j.
The price is CA $405
CA $856 total
includes taxes & fees
Apr 16 - Apr 17
Tranquil Modern Farmhouse

WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
Cambridge
10.0 out of 10, Exceptional, (14 reviews)
"Second time staying at this lovely, serene home/property. It’s the perfect getaway if you’re looking to escape into some peace! Highly recommend "
United States
Jill C.
The price is CA $403
CA $781 total
includes taxes & fees
Apr 14 - Apr 15
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

Waterfront Retreat | New Private Pier | Remodeled | Epic Sunset Views

Waterfront Retreat | New Private Pier | Remodeled | Epic Sunset Views
Lexington Park
10.0 out of 10, Exceptional, (7 reviews)
"Everything was very clean and well put together. Loved the view!"
United States
Minji S.
The price is CA $256
CA $548 total
includes taxes & fees
Apr 20 - Apr 21
Waterfront Retreat | New Private Pier | Remodeled | Epic Sunset Views

Modern Waterfront Home with Kayak, Firepit, Gameroom, Pool+Beaches, Dog & EV OK

Modern Waterfront Home with Kayak, Firepit, Gameroom, Pool+Beaches, Dog & EV OK
Montross
10.0 out of 10, Exceptional, (5 reviews)
"Beautiful home, very clean and comfy "
United States
Julie P.
The price is CA $248
CA $674 total
includes taxes & fees
Apr 13 - Apr 14
Modern Waterfront Home with Kayak, Firepit, Gameroom, Pool+Beaches, Dog & EV OK

Peaceful Waterfront Retreat for Bird Lovers- Close to DC

Peaceful Waterfront Retreat for Bird Lovers- Close to DC
Leonardtown
10.0 out of 10, Exceptional, (2 reviews)
"Beautiful property in a peaceful neighborhood. Great location! "
United States
R. L.
The price is CA $291
CA $643 total
includes taxes & fees
Apr 15 - Apr 16
Peaceful Waterfront Retreat for Bird Lovers- Close to DC

Waterfront Getaway with Dock

Waterfront Getaway with Dock
Woolford
10.0 out of 10, Exceptional, (54 reviews)
"Great place, will stay again"
United States
Matt S.
The price is CA $318
CA $386 total
includes taxes & fees
Apr 29 - Apr 30
Waterfront Getaway with Dock

Charming Waterfront 3-bedroom house in Piney Point

Charming Waterfront 3-bedroom house in Piney Point
Piney Point
10.0 out of 10, Exceptional, (2 reviews)
"Beautifully and tastefully decorated, immaculately clean, completely stocked top to bottom! You can tell by all of the details that these hosts care about curating a perfect stay for their guests. "
United States
Leslie K.
The price is CA $422
CA $817 total
includes taxes & fees
Apr 13 - Apr 14
Charming Waterfront 3-bedroom house in Piney Point

Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock

Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock
Lusby
10.0 out of 10, Exceptional, (1 review)
"We loved our stay! Lovely home, beautiful view"
United States
Sarah R.
The price is CA $617
CA $1,348 total
includes taxes & fees
Apr 13 - Apr 14
Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock

Fall is here!!! Backyard retreat waiting for you and your guest.

Fall is here!!! Backyard retreat waiting for you and your guest.
Waldorf
6.0 out of 10, (2 reviews)
"The property is beautiful. Furniture is comfortable (beds, sofa, and chairs). Everything was clean when we checked in. The patio/deck was beautiful. We were able to sit out back and enjoy the evening although it was chilly because of the heating lamp. It was a nice weekend gateway for the ladies - we are already planning the next one! I highly recommend staying here."
United States
Jackie P.
The price is CA $311
CA $577 total
includes taxes & fees
Apr 13 - Apr 14
Fall is here!!! Backyard retreat waiting for you and your guest.
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.
Save an average of 15% on thousands of hotels when you're signed in

Top St. Leonard Hotel Reviews

Find out more about St. Leonard

St. Leonard Vacation Homes information

Number of reviews
205
Accommodation
216 Vacation Homes
Lowest Price
CA $386
Highest Price
CA $1,348

Explore a world of travel with Expedia