St. Leonard Holiday Rentals

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Our top choices for St. Leonard holiday rentals

Soul Oasis - home on the Chesapeake Bay

Soul Oasis - home on the Chesapeake Bay
Lusby
10.0 out of 10, Exceptional, (50 reviews)
"Gorgeous. Host is very welcoming and available. Clear instructions, which are super helpful. Peaceful and stunning location. Thank you, Teresa!"
United States
Carver Z.
The price is NZ$502
includes taxes & fees
2 June - 3 June
Soul Oasis - home on the Chesapeake Bay

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 NZ$443
includes taxes & fees
31 May - 1 June
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.

Coles Point Marina

Coles Point Marina
2.0 star property
Hague
The price is NZ$533
includes taxes & fees
1 June - 2 June
Coles Point Marina

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

Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
Cambridge
10.0 out of 10, Exceptional, (16 reviews)
"Well equipped and super clean; great place!"
United States
Steve S.
The price is NZ$729
includes taxes & fees
1 June - 2 June
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)

Rustic 3BR Waterfront Cabin with Firepit + Dock Access

Rustic 3BR Waterfront Cabin with Firepit + Dock Access
Hague
The price is NZ$332
includes taxes & fees
31 May - 1 June
Rustic 3BR Waterfront Cabin with Firepit + Dock Access

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)
"Everything was exceptional! We will be back. "
United States
Kimberly F.
The price is NZ$546
includes taxes & fees
1 June - 2 June
Walk to Beach! King Bed & Free Beach Passes

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, (9 reviews)
"Everything was very clean and well put together. Loved the view!"
United States
Minji S.
The price is NZ$649
includes taxes & fees
1 June - 2 June
Waterfront Retreat, Private Pier, Remodeled, Epic Views, Sunsets on the River

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$459
includes taxes & fees
2 June - 3 June
Waterfront Getaway with Dock

Waterfront, Kayak, Beach, Game room, Potomac 2hr DC, Dogs+EV OK

Waterfront, Kayak, Beach, Game room, Potomac 2hr DC, Dogs+EV OK
Montross
10.0 out of 10, Exceptional, (5 reviews)
"Beautiful home, very clean and comfy "
United States
Julie P.
The price is NZ$793
includes taxes & fees
31 May - 1 June
Waterfront, Kayak, Beach, Game room, Potomac 2hr DC, Dogs+EV OK

Charming Waterfront 3-bedroom house in Piney Point

Charming Waterfront 3-bedroom house in Piney Point
Piney Point
10.0 out of 10, Exceptional, (3 reviews)
"Loved it! Wish we had more time to spend in the lovely rental. "
United States
Hilary B.
The price is NZ$974
includes taxes & fees
31 May - 1 June
Charming Waterfront 3-bedroom house in Piney Point

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$869
includes taxes & fees
31 May - 1 June
Beach Front, Bay View, Fishing, chesapeake,Family Getaway

Cottage Located on the Patuxent River!

Cottage Located on the Patuxent River!
Prince Frederick
10.0 out of 10, Exceptional, (43 reviews)
"The accommodations were superb and being on the water was amazing!"
United States
Daniel P.
The price is NZ$597
includes taxes & fees
4 June - 5 June
Cottage Located on the Patuxent River!

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$588
includes taxes & fees
5 June - 6 June
Bright and airy waterfront getaway

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)
"Amazing place to stay. Very Very clean ! Great location. Definitely will book this place again "
United States
Christy C.
The price is NZ$882
includes taxes & fees
31 May - 1 June
Anne & Fred`s Leonardtown Home W/ Arcade room!

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, (35 reviews)
"Everything was as expected, lovely spot even with lots of snow and ice!"
United States
Becky S.
The price is NZ$1,219
includes taxes & fees
11 June - 12 June
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

2 Bedroom Cottage at Coles Point Marina

2 Bedroom Cottage at Coles Point Marina
Hague
The price is NZ$701
includes taxes & fees
2 June - 3 June
2 Bedroom Cottage at Coles Point Marina

3-Bedroom Beach Home w/ Backyard

3-Bedroom Beach Home w/ Backyard
North Beach
The price is NZ$794
includes taxes & fees
4 June - 5 June
3-Bedroom Beach Home w/ Backyard

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, (5 reviews)
"Beautiful property in a peaceful neighborhood. Great location! "
United States
R. L.
The price is NZ$882
includes taxes & fees
2 June - 3 June
Peaceful Waterfront Retreat for Bird Lovers- Close to DC

Lakefront Cabin near Solomons Island w/ Hot Tub

Lakefront Cabin near Solomons Island w/ Hot Tub
Lusby
10.0 out of 10, Exceptional, (1 review)
"We had such a wonderful stay at Diana’s lake house! The view of the lake is absolutely beautiful waking up to that peaceful scenery every morning was one of the highlights of our trip.The property has a charming rustic feel while still offering all the amenities you could need. It felt cozy and comfortable, yet fully equipped for a relaxing getaway. We especially loved being able to kayak right from the area such a perfect way to enjoy the water and the surroundings.Diana was an exceptional...
United States
rakesh s.
The price is NZ$1,621
includes taxes & fees
29 June - 30 June
Lakefront Cabin near Solomons Island w/ Hot Tub
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

Everything you need to know about St. Leonard holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the St. Leonard holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect St. Leonard holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

St. Leonard holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in St. Leonard. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A St. Leonard holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of St. Leonard holiday rentals we have selected for you start as low as NZ$443 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on St. Leonard rentals

At Expedia, we put the best St. Leonard holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top St. Leonard rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream St. Leonard holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around St. Leonard. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

Waterfront Tilghman Retreat with Dock, Fire Pit & Sunsets: This holiday home rental outside of St. Leonard is located on a river, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of games in this rental home to help you unwind.

How many holiday rentals are there in St. Leonard?

With 18 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.