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Top Holiday Rentals in St. Leonard

Waterfront house with private beach and pier
9.8 out of 10, Exceptional, (12)
"An amazing, secluded property that is perfect for a family or friends getaway. The rooms are clean, comfortable, and there were plenty of bathrooms. The property could improve by having additional toilet paper, shower toiletries, and towels, but the kitchen was very well stocked and there was plenty of seating. It really is a great house."
Waterfront house with private beach and pier
Welcome to Hickory House on the Chesapeake Bay!
9.6 out of 10, Exceptional, (19)
"Had a great week! Cottage is adorable, clean and cozy. Host very welcoming with treats and bowls for our dogs. House is a couple weeks from the beach and a beach parking pass is included. The beach is private and very relaxing. It was very hot that week that we visited abd tge AC was excellent. Lots of extras in the house - games, hand soaps and even ballth salts! Very enjoyable visit!"
Welcome to Hickory House on the Chesapeake Bay!
Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing
9.8 out of 10, Exceptional, (107)
"The property is located in a small neighborhood right by the water. While there are houses fairly close it is quiet with beautiful views. The house is clean and has good appliances/wifi for a comfortable stay. It is a one bedroom with a big bathroom and living room. The screened in patio is good to avoid the mosquitos. One note is for those with mobility issues, the shower/bathtub has a high ledge with a thicker width to get in/out."
The price is £228
per night
17 Jun - 18 Jun
Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing
Waterfront Cottage in Beautiful Hoopers Island
10.0 out of 10, Exceptional, (54)
"We have stayed at this property twice and love it. Very peaceful, clean, and comfortable."
Waterfront Cottage in Beautiful Hoopers Island
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!
9.6 out of 10, Exceptional, (4)
"We extremely enjoyed our stay. The house was beautiful, kitchen was well equipped and the view was spectacular, especially with the Eagles that have nested on the 32 acre property. However was disappointed in the fact that the fire places were not in working conditions and rooms should have been number. We enjoy kayaking up and down the bay and taking it all in. I would definitely stay again."
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!
Piney Point, private , Beach Front Cottage
10.0 out of 10, Exceptional, (76)
"We are so grateful to have had some time in this wonderful home. It was amazing to have the water at our back door. Every member of the family loved our stay here. Thank you so much!"
Piney Point, private , Beach Front Cottage
The Normandy Cottage ~ Charming Getaway ~ On The Shores Of The Chesapeake!
9.6 out of 10, Exceptional, (35)
"Great place for a short moms getaway. Walking distances to many things. Heard live music from the porch. House is spacious and extremely clean"
The Normandy Cottage ~ Charming Getaway ~ On The Shores Of The Chesapeake!
Beautiful Waterfront Retreat in Cambridge!
10.0 out of 10, Exceptional, (18)
"We enjoyed our trip, the house was fully equipped and had all the comforts you could need. The water view, watching the birds, the kayak, the dock at sunrise, were our favorite things. We look forward to coming back sometime soon."
The price is £404
per night
16 Jun - 17 Jun
Beautiful Waterfront Retreat in Cambridge!
Breathtaking Views, 450 pier, kayaks, fossils, priv beach, 45 min to D.C.
10.0 out of 10, Exceptional, (102)
"Loved the house!"
Breathtaking Views, 450 pier, kayaks, fossils, priv beach, 45 min to D.C.
Soul Oasis - home on the Chesapeake Bay
10.0 out of 10, Exceptional, (6)
"Pleasant relaxing time. We were pleased and impress to locate this property"
The price is £231
per night
17 Jun - 18 Jun
Soul Oasis - home on the Chesapeake Bay
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
10.0 out of 10, Exceptional, (25)
"I chose to stay at this property for the duration of my wedding weekend. It was really great to be able to spend that extra time with family all together! Getting ready at the house, rather than a hotel was also really nice because we had much more room to space out. The make up artist and hair stylist also complimented the ample natural light and space to work. The pool and hot tub were beautiful! The only downside was a lack of curtains in the master bedroom. The sunrise is beautiful but...
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
Maryland Vacation Rental w/ Private Pool & Dock
10.0 out of 10, Exceptional, (4)
"Had a great time fishing from the dock while we got out of the city for a weekend."
Maryland Vacation Rental w/ Private Pool & Dock
Waterfront Relaxing Getaway
10.0 out of 10, Exceptional, (11)
"I was looking for a nice, quiet, and relaxing, vacation. This property did not disappoint. The house was comfortable, cozy, well stocked, and so clean. The view is incredible. Just sitting outside watching the river was so "Zen". I had one of the most restful vacations ever. I was there for a little over two weeks and I would have stayed longer if I could have, Kim, the host, was very friendly and helpful. I look forward to staying at this beautiful property again."
The price is £336
per night
16 Jun - 17 Jun
Waterfront Relaxing Getaway
Bay view from Calvert Cliffs, Solomons Island & State Park nearby
10.0 out of 10, Exceptional, (29)
"👍👍"
Bay view from Calvert Cliffs, Solomons Island & State Park nearby
Waterfront Lusby Retreat w/ Deep-Water Dock & Slip
10.0 out of 10, Exceptional, (4)
"We were in town for a friends wedding. This was the perfect location as it was right in between the Catholic Church for the nuptial mass and the reception site. This place certainly did not disappoint. There was plenty of space for our large family, the home was well equipped and stocked with the necessary items. It was a relatively short stay, but I wish we had a bit more time and better weather to enjoy the use of kayaks - our one free morning was a bit chilly for us Florida folks, and we had...
Waterfront Lusby Retreat w/ Deep-Water Dock & Slip
Cozy Virginia Potomac Riverfront Cottage
9.6 out of 10, Exceptional, (24)
"We had a wonderful stay. The house was just as described, a cozy cottage perfect for relaxing with beautiful riverfront views. The kitchen was stocked with everything we needed, the living room and main bedroom we used were comfortable, and the sun porch had great views where you could relax in the AC. The patio had a great dining table/umbrella, and the dock was perfect for fishing. Thank you for a lovely getaway cottage!"
Cozy Virginia Potomac Riverfront Cottage
The Schultz Estate
9.6 out of 10, Exceptional, (5)
"This house is great for large groups with plenty of comfortable bedrooms, three bathrooms (note one is only a tub, no shower), and loads of outdoor seating and fire options. This is an old farmhouse, so quirks of an old wooden house on the Eastern shore come with that. Personal bug spray at this property is essential as the mosquitos are very intense. The owner did stop by to give us a lawn spray for them but we did not use it as I am a master naturalist and community garden manager who is...
The Schultz Estate
Spacious River Front Home - 90 minutes from DC with Dock, Kayaks & Paddleboards
9.8 out of 10, Exceptional, (15)
"We booked a long weekend for our daughter’s graduation from St Mary’s. The house was beautiful and so spacious for our adult children and grandchildren to all be in one location without feeling cramped. We loved having the fire pit and room to throw a football around. Thank you for sharing your home Victoria!"
Spacious River Front Home - 90 minutes from DC with Dock, Kayaks & Paddleboards
The Blue Crab Beach House - Free beach passes
10.0 out of 10, Exceptional, (39)
"It was clean and had everything we needed. We had a very comfortable stay. There are one or two steps between many of the rooms so keep that in mind."
The Blue Crab Beach House - Free beach passes
Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp
10.0 out of 10, Exceptional, (51)
"What a fantastic property! We loved staying here and our family had such a great time exploring. Sadly it was a drizzly, dreary weekend but we had one nice day to go down to the beach and the kids enjoyed playing in the water. We loved the variety of porches to sit on and have different views and there was plenty of room for the kids to play indoors when it was raining. Overall a great experience. Thank you!"
Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp
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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.

Other types of properties in St. Leonard you may be interested in

Welcome to Hickory House on the Chesapeake Bay!
9.6 out of 10, Exceptional, (19)
"Had a great week! Cottage is adorable, clean and cozy. Host very welcoming with treats and bowls for our dogs. House is a couple weeks from the beach and a beach parking pass is included. The beach is private and very relaxing. It was very hot that week that we visited abd tge AC was excellent. Lots of extras in the house - games, hand soaps and even ballth salts! Very enjoyable visit!"
Welcome to Hickory House on the Chesapeake Bay!
La Quinta Inn & Suites by Wyndham Lexington Park - Patuxent
2.5 star property
7.6 out of 10, Good, (1001)
"The front desk was very polite, responsibe and professional. When we first arrived our room was fine but the beds were made with dirty covers and they swiftly moved us to another room. The room was fine and a little on the smaller side (we are a family of 4 and we made it work) i did wake up with one single bite on my leg that is suspicious so well be steaming all of our things (we always try to do that anyway when we stay in any hotel. The pool was clean and the exercise room was great. The...
The price is £84
per night
4 Jul - 5 Jul
La Quinta Inn & Suites by Wyndham Lexington Park - Patuxent
Rod 'N' Reel Resort
3.0 star property
8.2 out of 10, Very good, (1001)
"Under construction indoor fun stuff not available they did have outdoor kid games available but we don’t have kids. Mini convenience store had no ice cream 1936 bar & grill which rod & reel recommended not good over priced don’t go there other hrs opened late closed early "
The price is £180
per night
16 Jun - 17 Jun
Rod 'N' Reel Resort
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.

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, apart-hotels, 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 £228 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?

Welcome to Hickory House on the Chesapeake Bay!: This highly rated holiday home rental in St. Leonard is located near the beach, and has a fireplace, a patio and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals are there in St. Leonard?

With 17 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?

Jefferson Patterson Park and Museum and Patuxent River are a couple of lovely local spots to get outside and enjoy nature. In the wider area, you’ll find Perigeaux Vineyards and Winery and Calvert Cliffs State Park.

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.

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