St. Leonard Holiday Rentals

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Our top choices for St. Leonard holiday rentals

9.6 out of 10, Exceptional, (4 reviews)
"Great place in a wonderful area! So cozy & well situated! A perfect weekend getaway!"
United States
Jana S.
The price is AU$438
includes taxes & fees
22 Jan - 23 Jan
Charming 2-bedroom 1 bath cottage with AC, WiFi in peaceful North Beach, Md.
9.8 out of 10, Exceptional, (40 reviews)
"The cozy cabin had everything needed for a comfortable stay. It was in a very private setting with the beach access a few houses away. You can hear the Chesapeake bay lapping at the shore and catch a glimpse of sail boats going by. We enjoyed our time at the home."
United States
Mary G.
The price is AU$422
includes taxes & fees
25 Jan - 26 Jan
Soul Oasis - home on the Chesapeake Bay

Cabin in Hague

Coles Point Marina
2.0 star property
The price is AU$557
includes taxes & fees
22 Jan - 23 Jan
Coles Point Marina

Holiday Home in Solomons

4-BR Waterfront Turret Home
2.0 star property
10.0 out of 10, Exceptional, (7 reviews)
"Beautiful house. Beautiful scenery. Everything was perfect. "
United States
Thomas S.
The price is AU$1,088
includes taxes & fees
22 Jan - 23 Jan
4-BR Waterfront Turret Home
3.0 star property
The price is AU$1,244
includes taxes & fees
22 Jan - 23 Jan
Lakefront Log Cabin Retreat w/ Hot tub + Kayaks!

Cottage in Prince Frederick

Cottage Located on the Patuxent River!
10.0 out of 10, Exceptional, (42 reviews)
"This place was very lovely. Beautiful atmosphere and very spacious cottage. Didn’t get to see the owners but really enjoyed their property. Loved having the coffee maker, comfy bed and awesome tub! I will definitely be back. "
United States
RACHEL S.
The price is AU$475
includes taxes & fees
25 Jan - 26 Jan
Cottage Located on the Patuxent River!
10.0 out of 10, Exceptional, (31 reviews)
"Perfect place to spend quality time with our three adult children and their significant others. "
United States
Malarkey F.
The price is AU$578
includes taxes & fees
22 Jan - 23 Jan
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
10.0 out of 10, Exceptional, (18 reviews)
"We loved our stay! The property was just as advertised and had everything we needed. Quiet area and felt very safe. The owners provided excellent communication as well!"
United States
Jennifer B.
The price is AU$458
includes taxes & fees
22 Jan - 23 Jan
Walk to Beach! King Bed & Free Beach Passes
10.0 out of 10, Exceptional, (1 review)
"Beautiful newly renovated space with all new appliances, furniture and kitchenware. Comfortable beds, and super clean rooms. Large outside area with new Weber grill, fire pit, and three kayaks. Nice easy to access dock. "
United States
Kit C.
The price is AU$855
includes taxes & fees
22 Jan - 23 Jan
Charming Waterfront 3-bedroom house in Piney Point
10.0 out of 10, Exceptional, (5 reviews)
"We enjoyed this house fully for our Thanksgiving stay! We even took the canoes out for a spin. Nice walks around the development and the beach area is lovely. "
United States
Julie I.
The price is AU$589
includes taxes & fees
22 Jan - 23 Jan
Modern Waterfront Home with Kayak, Firepit, Gameroom, Pool+Beaches, Dog & EV OK
10.0 out of 10, Exceptional, (1 review)
"We loved our stay! Lovely home, beautiful view"
United States
Sarah R.
The price is AU$1,270
includes taxes & fees
22 Jan - 23 Jan
Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock
9.0 out of 10, Wonderful, (8 reviews)
"The owner was very nice "
United States
karen
The price is AU$447
includes taxes & fees
22 Jan - 23 Jan
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.

Holiday Home in Woolford

Waterfront Getaway with Dock
10.0 out of 10, Exceptional, (51 reviews)
"Great place, will stay again"
United States
Matt S.
The price is AU$412
includes taxes & fees
27 Jan - 28 Jan
Waterfront Getaway with Dock
10.0 out of 10, Exceptional, (50 reviews)
"The house was completely spotless - the location was perfect! And the host included a s'mores kit, and baited crab traps and had them waiting with crabs in them when we arrived! This was an excellent weekend - we would recommend Hudson House to anyone!"
United States
Elizabeth G.
The price is AU$538
includes taxes & fees
25 Jan - 26 Jan
Beautiful Waterfront Retreat in Cambridge!
10.0 out of 10, Exceptional, (8 reviews)
"Everything was amazing. "
United States
Lorie S.
The price is AU$600
includes taxes & fees
25 Jan - 26 Jan
2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!
2.0 star property
The price is AU$423
includes taxes & fees
2 Feb - 3 Feb
2 Bedroom Cottage at Coles Point Marina

Holiday Home in Leonardtown

Potomac Vista Cottage
2.0 star property
The price is AU$517
includes taxes & fees
25 Jan - 26 Jan
Potomac Vista Cottage
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 AU$532
includes taxes & fees
2 Feb - 3 Feb
Waterfront Escape | Family-Friendly | Remodeled Home | Epic Sunset Views | Decks
9.2 out of 10, Wonderful, (5 reviews)
"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."
United States
Lauren A.
The price is AU$863
includes taxes & fees
26 Jan - 27 Jan
Anne & Fred`s Leonardtown Home W/ Arcade room!
10.0 out of 10, Exceptional, (14 reviews)
"Amazing news out of the back.Great for kayaking.We brought our own kayaksAnd also use yoursThere were four of usWe also took a nice trip over to Saint Michael’s"
United States
Sandy S.
The price is AU$788
includes taxes & fees
23 Jan - 24 Jan
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
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 favourite 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 depend 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 AU$422 per night. Entering your travel dates in the search wizard might find you 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?

Beach Combing & Relaxation: This highly rated holiday home rental in St. Leonard is located in a rural location, and has a patio, a selection of games 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.

How many holiday rentals are there in St. Leonard?

With 15 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 Flag Ponds Nature Park are a couple of lovely local spots to get outside and enjoy nature. Other places in town to visit include Flag Harbor Marina and Northern Chesapeake Bay.

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.