St. Leonard Vacation Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
Aug 29 - Aug 31
In two weeks
Sep 5 - Sep 7
In one month
Sep 19 - Sep 21
In two months
Oct 17 - Oct 19

Browse Select St. Leonard Vacation Homes

Waterfront Getaway with Dock
Fridge, microwave, oven, stovetop

Waterfront Getaway with Dock

10.0 out of 10, Exceptional, (49)
"Fit all of our needs. Clean,well furnished, nice kitchen. Stayed there twice and will probably go back."
The price is CA $317
CA $385 total
includes taxes & fees
Aug 25 - Aug 26
Waterfront Getaway with Dock
Beach Home with King Bed and Beach Passes in a Cute Town
Beach nearby

Beach Home with King Bed and Beach Passes in a Cute Town

10.0 out of 10, Exceptional, (16)
"Excellent"
The price is CA $131
CA $472 total
includes taxes & fees
Aug 24 - Aug 25
Beach Home with King Bed and Beach Passes in a Cute Town
Riverside Dreams -golfcart-views-screened porch-
Fridge, microwave, oven, stovetop

Riverside Dreams -golfcart-views-screened porch-

2.0 star property
10.0 out of 10, Exceptional, (2)
"We found the view and the accommodations quite lovely."
The price is CA $157
CA $543 total
includes taxes & fees
Sep 3 - Sep 4
Riverside Dreams -golfcart-views-screened porch-
Family Beach House: Spacious Deck, Grill & Views
Pool

Family Beach House: Spacious Deck, Grill & Views

9.0 out of 10, Wonderful, (6)
"Everything was great. The owner was extremely helpful. Couldn't ask for anything better."
The price is CA $199
CA $552 total
includes taxes & fees
Sep 15 - Sep 16
Family Beach House: Spacious Deck, Grill & Views
Huge Beach Bungalow w/Yard, Beach Passes, 2 King Bds near Boardwalk, Restaurants
Beach nearby

Huge Beach Bungalow w/Yard, Beach Passes, 2 King Bds near Boardwalk, Restaurants

10.0 out of 10, Exceptional, (28)
"Absolutely beautiful and spacious home perfectly located in North Beach. Very peaceful area and close to the beach, restaurants and shopping. We really enjoyed our stay and hope to visit again in the future. "
The price is CA $274
CA $738 total
includes taxes & fees
Aug 24 - Aug 25
Huge Beach Bungalow w/Yard, Beach Passes, 2 King Bds near Boardwalk, Restaurants
Anne & Fred's Leonardtown Home
Fridge, microwave, oven, stovetop

Anne & Fred's Leonardtown Home

9.4 out of 10, Exceptional, (3)
"Nice place to stay. Perfect location for our needs. Suggest noting the hot and cold water flip upstairs, and to add a mirror in the hallway by outlet for blow dryer."
The price is CA $345
CA $757 total
includes taxes & fees
Aug 24 - Aug 25
Anne & Fred's Leonardtown Home
The Hidaway on the Patuxent River<br>Children allowed and welcomed to stay.
Outdoor dining

The Hidaway on the Patuxent River<br>Children allowed and welcomed to stay.

9.2 out of 10, Wonderful, (9)
"Got to go fishing, kayaking, and swimming in the pool. Had a great time, views are wonderful and it’s a peaceful environment. 10/10 would stay again."
The price is CA $279
CA $665 total
includes taxes & fees
Sep 1 - Sep 2
The Hidaway on the Patuxent River<br>Children allowed and welcomed to stay.
Kick back and enjoy the Chesapeake & this 3-bedroom, calm, stylish space.
3 bedrooms, iron/ironing board, travel crib, free WiFi

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

9.4 out of 10, Exceptional, (3)
"We had a short stay after a sporting event in DC, it was a little less than an hour away. Convenient location and a very clean house. Kitchen was well stocked. There was little communication with the owner, which was nice vs a long list of rules, but we would have liked to know any of their local specific favorite spots or more detailed check in/check out. Worked out nicely for our family. "
The price is CA $291
CA $556 total
includes taxes & fees
Aug 25 - Aug 26
Kick back and enjoy the Chesapeake & this 3-bedroom, calm, stylish space.
High River Bank with $1M Sunset View, 3 min to College
Terrace/patio

High River Bank with $1M Sunset View, 3 min to College

10.0 out of 10, Exceptional, (2)
"This was our second time staying at this beautiful home, and it was just as wonderful as we remembered. The house is impeccably maintained, tastefully decorated, and incredibly comfortable. The beds are cozy, and every detail has been thoughtfully considered—from the clear labels throughout the home to the fully stocked kitchen and amenities. It truly feels like a home away from home. We had a fantastic stay and are already looking forward to our next visit!"
The price is CA $316
CA $630 total
includes taxes & fees
Aug 21 - Aug 22
High River Bank with $1M Sunset View, 3 min to College
Beautiful Waterfront Retreat in Cambridge!
Interior

Beautiful Waterfront Retreat in Cambridge!

10.0 out of 10, Exceptional, (43)
"Our kids enjoyed the games in the crab house. It was great being able to use the kayaks and life vests."
The price is CA $333
CA $650 total
includes taxes & fees
Aug 27 - Aug 28
Beautiful Waterfront Retreat in Cambridge!
Sunset Breezes - quiet waterfront retreat
Property grounds

Sunset Breezes - quiet waterfront retreat

10.0 out of 10, Exceptional, (39)
"Good time with my friends "
The price is CA $446
CA $559 total
includes taxes & fees
Aug 26 - Aug 27
Sunset Breezes - quiet waterfront retreat
Tranquil Modern Farmhouse
Fridge, microwave, stovetop, dishwasher

Tranquil Modern Farmhouse

9.4 out of 10, Exceptional, (6)
"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! "
The price is CA $311
CA $730 total
includes taxes & fees
Aug 24 - Aug 25
Tranquil Modern Farmhouse
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
Smart TV

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

10.0 out of 10, Exceptional, (13)
"very serene, peaceful home on the bay! Amazing getaway! "
The price is CA $481
CA $855 total
includes taxes & fees
Aug 22 - Aug 23
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
Roomy 6 bedroom home in the heart of Solomons, MD
Microwave, oven, stovetop, dishwasher

Roomy 6 bedroom home in the heart of Solomons, MD

9.2 out of 10, Wonderful, (5)
"Stayed for business, completed our project and enjoyed some local eating spots. "
The price is CA $585
CA $1,017 total
includes taxes & fees
Aug 24 - Aug 25
Roomy 6 bedroom home in the heart of Solomons, MD
BRAND NEW waterfront Retreat in beautiful Montross, Virginia
Dining

BRAND NEW waterfront Retreat in beautiful Montross, Virginia

10.0 out of 10, Exceptional, (1)
"Beautiful home, very clean and has amazing views. Check in was easy and the owners were very easy to get ahold of. Fantastic vacation in a great location and fantastic home. "
The price is CA $441
CA $979 total
includes taxes & fees
Sep 3 - Sep 4
BRAND NEW waterfront Retreat in beautiful Montross, Virginia
Charming Waterfront 3-bedroom house in Piney Point
Property grounds

Charming Waterfront 3-bedroom house in Piney Point

The price is CA $394
CA $766 total
includes taxes & fees
Sep 7 - Sep 8
Charming Waterfront 3-bedroom house in Piney Point
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
Sign in
Sign up, it's free

Top St. Leonard Hotel Reviews

Solomons Inn Resort & Marina

Solomons Inn Resort & Marina

10/10 Excellent
"The staff was very friendly, the rooms were clean, they are remodeling. The one disappointment for me was Pet Friendly and some people's pet aren't clean."
Carolyn 2-night trip
Posted 2 days ago
Solomons Inn Resort & Marina