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Top Holiday Rentals in St. Leonard

Outdoor dining
The Schultz Estate
10.0 out of 10, Exceptional, (4)
"Had a great stay! Beautiful location! House was clean roomy, overall had a great time! The only thing I would say is work on the doors closing. In restrooms."
The Schultz Estate
Property grounds
Waterfront Cottage in Beautiful Hoopers Island
10.0 out of 10, Exceptional, (53)
"Had a wonderful time really enjoyed the use of the dock the house was perfect had everything you could of possibly needed definitely will be back!"
Waterfront Cottage in Beautiful Hoopers Island
Beach
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 £338
includes taxes & fees
2 Jun - 3 Jun
Waterfront Relaxing Getaway
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Beach | Beach nearby, sun-loungers
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
Exterior
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 £229
includes taxes & fees
27 May - 28 May
Soul Oasis - home on the Chesapeake Bay
Smart TV, fireplace
Bay view from Calvert Cliffs, Solomons Island & State Park nearby
10.0 out of 10, Exceptional, (29)
"The house was great and nice area!"
Bay view from Calvert Cliffs, Solomons Island & State Park nearby
Beach nearby, sun-loungers, beach umbrellas, beach towels
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
3 bedrooms, desk, iron/ironing board, free WiFi
Breathtaking Views, 450 pier, kayaks, fossils, priv beach, 45 min to D.C.
10.0 out of 10, Exceptional, (101)
"Really enjoyed our time there. Very relaxing. Comfortable home. All amenities there. Especially loved the windows..."
Breathtaking Views, 450 pier, kayaks, fossils, priv beach, 45 min to D.C.
Property grounds
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
10.0 out of 10, Exceptional, (23)
"This house and property is GORGEOUS. Well maintained, beautiful setting. Amazing amenities (pool, hot tub) which enhanced our stay. We had no problem finding multiple places to all hang out and chat- the living room with plenty of seating, the dining room table with seating for at least 14, and outside in the hot tub. It was a perfect setting for valuable time away with friends! Additionally, the owner was STELLAR in communication. I very much appreciated his quick and attentive responses...
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
Property grounds
Maryland Vacation Rental w/ Private Pool & Dock
10.0 out of 10, Exceptional, (4)
"Loved the house and kids loved the pool. We also managed to catch a half dozen crabs (August trip). House is on the smaller side, but with four bedrooms everyone had privacy and just what they needed. We'll be back!"
Maryland Vacation Rental w/ Private Pool & Dock
Fridge, microwave, oven, stovetop
Stunning Waterfront Maryland Eastern Shore Home with In-Ground Pool and Hot Tub
10.0 out of 10, Exceptional, (31)
"One of the best properties I have stayed at. With all the amenities, you never need to leave the home. We enjoyed the views, the quietness of the area, and the wildlife. We nicknamed two beautiful ducks…Sonny and Cher! The house is very clean, the checkin checkout procedures were very easy. The host communicated all the details plus additional suggestions. We are definitely returning very soon."
Stunning Waterfront Maryland Eastern Shore Home with In-Ground Pool and Hot Tub
Property grounds
The Lazy Crab Beach House - Free beach passes
10.0 out of 10, Exceptional, (23)
"The Lazy Crab was a wonderful place to stay for a girls weekend away! Everything was provided to make the stay easy, comfortable and fun! If we needed it it was there. The location was perfect… great restaurants right down the street and the bay just beyond… an easy walk away. The owner was responsive when we messaged. All good and I would stay again. Thank you!"
The Lazy Crab Beach House - Free beach passes
Property grounds
Mid-Century Modern and Marvelous on the Bay
10.0 out of 10, Exceptional, (61)
"The house was lovely. We had 3 days of rain but the view and the beach made it interesting at all times. The hosts make sure you have everything you need for your comfort and entertainment. This is by far the best appointed house we have rented. Thank you for a wonderful week!"
Mid-Century Modern and Marvelous on the Bay
Beach
Belle of the Chesapeake Bay
10.0 out of 10, Exceptional, (2)
"The property was very clean and nicely appointed."
Belle of the Chesapeake Bay
Pool
Beach Front, Bay View, Fishing, chesapeake,Family Getaway
10.0 out of 10, Exceptional, (1)
"The house was clean and quiet. The hosts were helpful and available for communication. This is a lovely house for a vacation away from crowds and by the beach."
The price is £425
includes taxes & fees
3 Jun - 4 Jun
Beach Front, Bay View, Fishing, chesapeake,Family Getaway
Fridge, microwave, oven, stovetop
Beautiful Waterfront Retreat in Cambridge!
10.0 out of 10, Exceptional, (16)
"We had a very enjoyable and relaxing stay here for Mother's Day weekend, coming in from DC. The property is in a great spot on the water and is a short ride into town. The house itself is cozy, clean, and welcoming with everything you need (including the crab house out back, which our four year old loved!) Rebecca is a thoughtful and accommodating host, too. She gave us several recommendations for food in the area and we really enjoyed her suggested restaurants in Cambridge and in Easton on the...
The price is £380
includes taxes & fees
27 May - 28 May
Beautiful Waterfront Retreat in Cambridge!
Property grounds
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
Property grounds
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 £194
includes taxes & fees
23 May - 24 May
Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing
Fridge, microwave, stovetop, dishwasher
Updated North Beach Cottage: Pet Friendly!
9.8 out of 10, Exceptional, (8)
"This location was perfect for our trip for a wedding. Being only a three minute walk from the rehearsal, ceremony, and reception was absolutely perfect. Being close to the deli/market as well came in handy. The house was clean and welcoming. Overall I would absolutely stay here again."
Updated North Beach Cottage: Pet Friendly!
Pool
Waterfront Insta-Worthy Sunsets! 5BR w/ Bikes , Kayaks and 🐾 Friendly
9.8 out of 10, Exceptional, (116)
"Great house close to the lodge!"
The price is £675
includes taxes & fees
30 May - 31 May
Waterfront Insta-Worthy Sunsets! 5BR w/ Bikes , Kayaks and 🐾 Friendly
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See all available properties in St. Leonard
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

Beach nearby, sun-loungers, beach towels
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!
Superior Studio Suite | Balcony
Rod 'N' Reel Resort
3.0 star property
8.2 out of 10, Very good, (1000)
"Charged a $20 Resort fee but all I did was sleep there."
The price is £120
includes taxes & fees
23 May - 24 May
Rod 'N' Reel Resort
Premium bedding, desk, blackout curtains, iron/ironing board
La Quinta Inn & Suites by Wyndham Lexington Park - Patuxent
2.5 star property
7.6 out of 10, Good, (1002)
"Great place for the price ! Perfect for business Clean and great guest service. Including breakfast for early birds on business. Thanks "
The price is £68
includes taxes & fees
27 May - 28 May
La Quinta Inn & Suites by Wyndham Lexington Park - Patuxent
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 £219 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.

Recent reviews of St. Leonard properties
Expedia verified reviews

Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn

5/5 Excellent
"Excellent Inn and Marina. Perfect for boaters and people fishing the area. It’s also a nice place outside of St Michaels. The two main restaurants in the area need attention. The breakfast restaurant on the island “Two if by Sea” is excellent!"
A verified traveller stayed at Knapps Narrows Marina & Inn
Posted 2 days ago
Knapps Narrows Marina & Inn