St. Leonard Holiday Rentals

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Check prices for these dates

In two weeks
10 Apr - 12 Apr
In two months
22 May - 24 May
In three months
19 Jun - 21 Jun
In four months
17 Jul - 19 Jul

Our top choices for St. Leonard holiday rentals

Exterior

Soul Oasis - home on the Chesapeake Bay

Soul Oasis - home on the Chesapeake Bay
Lusby
10.0 out of 10, Exceptional, (42 reviews)
"The guidebook binder at the property helpfully had details about the Soul Oasis, like how to operate the heaters and fireplace, and suggested local spots and restaurants to visit. Also, the kitchen conveniently had many pots and pans and tools. The view of the water was a highlight!"
United States
Bronwen C.
The price is HK$978
HK$2,190 total
includes taxes & fees
8 Apr - 9 Apr
Soul Oasis - home on the Chesapeake Bay
Property grounds

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

Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Benedict
9.0 out of 10, Wonderful, (8 reviews)
"The location was perfect. It was quiet and clean with a wonderful view of the water, especially the sunrise through the bedroom window in the morning. The host kept in touch to answer any questions we had, and made sure our stay was great. We will absolutely be back!"
United States
Coulter L.
The price is HK$1,196
HK$2,089 total
includes taxes & fees
30 Mar - 31 Mar
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Exterior

Coles Point Marina

Coles Point Marina
2.0 star property
Hague
The price is HK$2,082
HK$2,930 total
includes taxes & fees
28 Mar - 29 Mar
Coles Point Marina
Pool

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 HK$1,329
HK$3,420 total
includes taxes & fees
30 Mar - 31 Mar
Beach Front, Bay View, Fishing, chesapeake,Family Getaway
Smart TV, books

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 HK$1,571
HK$3,298 total
includes taxes & fees
30 Mar - 31 Mar
Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.
Beach nearby

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 HK$929
HK$2,833 total
includes taxes & fees
12 Apr - 13 Apr
Walk to Beach! King Bed & Free Beach Passes
Sun-loungers

Cottage Located on the Patuxent River!

Cottage Located on the Patuxent River!
Prince Frederick
10.0 out of 10, Exceptional, (42 reviews)
"The accommodations were superb and being on the water was amazing!"
United States
Daniel P.
The price is HK$2,076
HK$2,482 total
includes taxes & fees
28 Mar - 29 Mar
Cottage Located on the Patuxent River!
Interior

Lakefront Log Cabin Retreat w/ Hot tub + Kayaks!

Lakefront Log Cabin Retreat w/ Hot tub + Kayaks!
3.0 star property
Lusby
The price is HK$1,869
HK$5,444 total
includes taxes & fees
31 Mar - 1 Apr
Lakefront Log Cabin Retreat w/ Hot tub + Kayaks!
Smart TV, books

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 HK$2,736
HK$5,987 total
includes taxes & fees
30 Mar - 31 Mar
4-BR Waterfront Turret Home
Beach

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 HK$2,041
HK$3,845 total
includes taxes & fees
31 Mar - 1 Apr
2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!
Living area

2 Bedroom Cottage at Coles Point Marina

2 Bedroom Cottage at Coles Point Marina
Hague
The price is HK$1,876
HK$2,322 total
includes taxes & fees
28 Mar - 29 Mar
2 Bedroom Cottage at Coles Point Marina
Fridge, microwave, oven, stovetop

Anne & Fred`s Leonardtown Home W/ Arcade room!

Anne & Fred`s Leonardtown Home W/ Arcade room!
Leonardtown
9.4 out of 10, Exceptional, (6 reviews)
"It was very comfortable felt like home "
United States
Carol S.
The price is HK$1,759
HK$4,357 total
includes taxes & fees
7 Apr - 8 Apr
Anne & Fred`s Leonardtown Home W/ Arcade room!
Interior

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, (5 reviews)
"Everything was very clean and well put together. Loved the view!"
United States
Minji S.
The price is HK$1,251
HK$2,858 total
includes taxes & fees
30 Mar - 31 Mar
Waterfront Retreat | New Private Pier | Remodeled | Epic Sunset Views
Fridge, microwave, oven, stovetop

Waterfront Getaway with Dock

Waterfront Getaway with Dock
Woolford
10.0 out of 10, Exceptional, (53 reviews)
"Great place, will stay again"
United States
Matt S.
The price is HK$1,798
HK$2,097 total
includes taxes & fees
31 Mar - 1 Apr
Waterfront Getaway with Dock
Outdoor dining

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.
Sunset Breezes - quiet waterfront retreat
Smart TV, fireplace, computer monitors, printers

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 HK$2,287
HK$4,796 total
includes taxes & fees
2 Apr - 3 Apr
Tranquil Modern Farmhouse
Smart TV

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 HK$2,384
HK$4,419 total
includes taxes & fees
19 Apr - 20 Apr
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
Outdoor dining

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 HK$1,304
HK$3,790 total
includes taxes & fees
22 Apr - 23 Apr
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
Property grounds

Come relax yourself a while

Come relax yourself a while
Mechanicsville
The price is HK$1,935
HK$4,614 total
includes taxes & fees
30 Mar - 31 Mar
Come relax yourself a while
Smart TV, books

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 HK$1,681
HK$3,635 total
includes taxes & fees
29 Mar - 30 Mar
Peaceful Waterfront Retreat for Bird Lovers- Close to DC
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

Comfort Inn & Suites Lexington Park near Pax River

Comfort Inn & Suites Lexington Park near Pax River

10/10 Excellent
"Easy access to Rt 4 Good cookies"
Edwin 1-night trip
Posted 2 days ago
Comfort Inn & Suites Lexington Park near Pax River

Find out more about St. Leonard

Search for holiday rentals in St. Leonard on Expedia! You can easily find your home rentals, villas, holiday apartments in St. Leonard using one of the methods below:

  • View our selection of featured holiday rentals in St. Leonard
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  • Enter your travel dates to view the best deals on holiday rentals in St. Leonard while they last

Look no further and take a look at our great range of rental properties in St. Leonard!

Frequently asked questions

Can I find a holiday rental in St. Leonard?

Yes, there are holiday rentals close to the most popular sights in St. Leonard, or you can select a more secluded option if you're looking for a relaxing stay. St. Leonard is known for its shopping and sporting events. Make sure you have time to check out the restaurants and wineries during your trip.

What are some of the best holiday rentals that St. Leonard has to offer?

Private 2 Acre Waterfront Family Retreat with Pool & Pier: This holiday home rental outside of St. Leonard is located on the waterfront, and has an outdoor pool, a balcony and a BBQ to put you at ease in your new surroundings. It has 8 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of books.

How many holiday rentals are there in St. Leonard?

With 16 Expedia holiday rentals, you're guaranteed to find just the right place for your St. Leonard stay.

What’s there to see and do in St. Leonard?

Matoaka Beach and Long Beach are a couple of lovely local spots to get outside and enjoy nature. Other places in town to visit include Flag Ponds Nature Park and Jefferson Patterson Park and Museum.

What’s a holiday rental in St. Leonard like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in St. Leonard. Holiday rentals feature extras like kitchens and laundry facilities so you'll have all the conveniences of home. If you're concerned about a sanitised environment, a holiday rental can offer a sense of security away from public hotel lifts and bustling concierge desks while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a great choice for family trips.