Holiday Homes in St. Leonard

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Our top choices for St. Leonard holiday homes

Walk to Beach! King Bed & Free Beach Passes

Walk to Beach! King Bed & Free Beach Passes
North Beach
10.0 out of 10, Exceptional, (20 reviews)
"Although the house itself could use some maintenance, our stay was very comfortable. The rooms were spacious and it had all the amenities we needed. "
United States
Donovan B.
The price is NZ$516
includes taxes & fees
10 May - 11 May
Walk to Beach! King Bed & Free Beach Passes

Beach Front, Bay View, Fishing, chesapeake,Family Getaway

Beach Front, Bay View, Fishing, chesapeake,Family Getaway
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 NZ$866
includes taxes & fees
20 May - 21 May
Beach Front, Bay View, Fishing, chesapeake,Family Getaway

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 NZ$763
includes taxes & fees
21 May - 22 May
Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.

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 NZ$775
includes taxes & fees
10 May - 11 May
2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!

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 NZ$898
includes taxes & fees
12 May - 13 May
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

Waterfront Retreat, Private Pier, Remodeled, Epic Views, Sunsets on the River

Waterfront Retreat, Private Pier, Remodeled, Epic Views, Sunsets on the River
Lexington Park
10.0 out of 10, Exceptional, (8 reviews)
"Everything was very clean and well put together. Loved the view!"
United States
Minji S.
The price is NZ$655
includes taxes & fees
25 May - 26 May
Waterfront Retreat, Private Pier, Remodeled, Epic Views, Sunsets on the River

Tranquil Modern Farmhouse

Tranquil Modern Farmhouse
Waldorf
9.0 out of 10, Wonderful, (8 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 NZ$1,120
includes taxes & fees
10 May - 11 May
Tranquil Modern Farmhouse

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 NZ$1,707
includes taxes & fees
25 May - 26 May
4-BR Waterfront Turret Home

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, (3 reviews)
"Beautiful property in a peaceful neighborhood. Great location! "
United States
R. L.
The price is NZ$730
includes taxes & fees
12 May - 13 May
Peaceful Waterfront Retreat for Bird Lovers- Close to DC

Bright and airy waterfront getaway

Bright and airy waterfront getaway
Benedict
9.6 out of 10, Exceptional, (20 reviews)
"Sophia was an amazing host and the place was exactly as advertised. I couldn't recommend the place enough!"
United States
William N.
The price is NZ$586
includes taxes & fees
11 May - 12 May
Bright and airy waterfront getaway

Waterfront Getaway with Dock

Waterfront Getaway with Dock
Woolford
10.0 out of 10, Exceptional, (57 reviews)
"Great place, will stay again"
United States
Matt S.
The price is NZ$463
includes taxes & fees
21 May - 22 May
Waterfront Getaway with Dock

Sunset Breezes - quiet waterfront retreat

Sunset Breezes - quiet waterfront retreat
Dorchester County
10.0 out of 10, Exceptional, (44 reviews)
"The place was vey clean, whic is of upmost improtance to me. We loved the veiw and the location."
United States
Crystal H.
The price is NZ$787
includes taxes & fees
27 May - 28 May
Sunset Breezes - quiet waterfront retreat

3-Bedroom Beach Home w/ Backyard

3-Bedroom Beach Home w/ Backyard
North Beach
The price is NZ$727
includes taxes & fees
14 May - 15 May
3-Bedroom Beach Home w/ Backyard

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 NZ$978
includes taxes & fees
14 May - 15 May
Charming Waterfront 3-bedroom house in Piney Point

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, (33 reviews)
"Perfect place to spend quality time with our three adult children and their significant others. "
United States
Malarkey F.
The price is NZ$1,230
includes taxes & fees
25 May - 26 May
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

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 NZ$1,647
includes taxes & fees
12 May - 13 May
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 NZ$689
includes taxes & fees
31 May - 1 June
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.
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Top St. Leonard Hotel Reviews

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St. Leonard Holiday Homes information

Number of reviews
221
Accommodation
226 Holiday Homes
Lowest Price
NZ$463
Highest Price
NZ$1,707