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Top Holiday Rentals in St. Leonard

New! Cozy River Cottage with great views of the water!

9.8 out of 10, Exceptional, (7)
"A very nice house with an amazing view 10/10 recommend"
New! Cozy River Cottage with great views of the water!

WATERFRONT!!! The River's Roost on The Patuxent River

10.0 out of 10, Exceptional, (22)
"Great stay, beautiful spot. We will be back for sure."
WATERFRONT!!! The River's Roost on The Patuxent River

Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing

9.8 out of 10, Exceptional, (135)
"Lovely, quiet, clean and comfy "
Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing

Waterfront Wildlife Retreat on the Patuxent River

10.0 out of 10, Exceptional, (165)
"The Waterfront Retreat on the Patuxent River is better than advertised. Our whole family stayed -- everyone loved it! It was clean, comfortable, with everything needed to stay comfortably, sleep, eat, relax and use as a home base for exploring. Solomons Island and the surrounding area was filled with lots of fun things to do (restaurant's, museums, history, boating, walking, etc.). "
Waterfront Wildlife Retreat on the Patuxent River

The Cozy Crab- Your Charming Haven in Lovely North Beach!

The Cozy Crab- Your Charming Haven in Lovely North Beach!

Family and Pet-Friendly, Waterfront with Pier

10.0 out of 10, Exceptional, (248)
"Our stay was great and Rob and Clarissa were very welcoming!"
Family and Pet-Friendly, Waterfront with Pier

Waterfront Cottage in Beautiful Hoopers Island

10.0 out of 10, Exceptional, (73)
"This is a small, sweet, comfortable cottage, and was just perfect for our brief getaway from the hurly-burly. The house is very well equipped, especially the kitchen, so cooking the local seafood was easy. The decor (loved the faux fireplace) was charming and welcoming, down to the live Poinsettia plant on the table when we got there. "
Waterfront Cottage in Beautiful Hoopers Island

Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

9.8 out of 10, Exceptional, (40)
"Beautiful, spacious, the highlight was the view of the bay. Definitely will be back"
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp

9.8 out of 10, Exceptional, (66)
"Property was exactly as advertised. Charming Farmhouse with plenty of space situated on a large property with a private beach. We even enjoyed some of the local restaurants, Captain Pat's Seafood and Tacos Haciendas."
Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp

Waterfront Solomons Apartment

9.4 out of 10, Exceptional, (9)
"The location is great with amazing views of the docks and very walkable to the boardwalk, restaurants, and the Solomon museum. Apartment was cozy with great communication from the hosts. Would recommend to anyone! "
The price is £212
includes taxes & fees
6 Jul - 7 Jul
Waterfront Solomons Apartment

The Blue Crab Beach House - Free beach passes

10.0 out of 10, Exceptional, (61)
"The property was well- maintained and the kitchen was well-equipped for our needs. Short walk to North Beach for dining and Boardwalk strolls. Nice and toasty for our winter stay - really enjoyed the trip."
The Blue Crab Beach House - Free beach passes

Beautiful Waterfront Retreat in Cambridge!

10.0 out of 10, Exceptional, (38)
"The house was so cute and the fact that we were able to do early check in was amazing!"
The price is £400
includes taxes & fees
1 Jul - 2 Jul
Beautiful Waterfront Retreat in Cambridge!

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

10.0 out of 10, Exceptional, (3)
"Perfect house for a long weekend. Clean, cozy and great communication with Maxine. Would definitely stay here again when I return to Cambridge. "
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)

Huge Beach Bungalow w/Yard, Beach Passes, 2 King Bds near Boardwalk, Restaurants

10.0 out of 10, Exceptional, (26)
"Everything about our stay was wonderful..the hosts were so quick to respond to any questions amd were very patient with me with all of my questions..I would DEFINITELY stay here again!!"
The price is £388
includes taxes & fees
30 Jun - 1 Jul
Huge Beach Bungalow w/Yard, Beach Passes, 2 King Bds near Boardwalk, Restaurants

Bay view from Calvert Cliffs, Solomons Island & State Park nearby

10.0 out of 10, Exceptional, (45)
"Awesome home wnd location! Would stay again!"
Bay view from Calvert Cliffs, Solomons Island & State Park nearby

The Lazy Crab Beach House - Free beach passes

10.0 out of 10, Exceptional, (52)
"Great stay"
The Lazy Crab Beach House - Free beach passes

Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.

10.0 out of 10, Exceptional, (44)
"We had a great stay! Thanks."
Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.

Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay

10.0 out of 10, Exceptional, (176)
"Great time!! Floridians playing in the snow!! Cozy fire afterwards in the fireplace. Picturesque drive up to the Navy Cabin, deer playing in the snow too."
Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay

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

9.4 out of 10, Exceptional, (3)
"The owner was very nice "
The price is £223
includes taxes & fees
30 Jun - 1 Jul
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.

Soul Oasis - home on the Chesapeake Bay

9.8 out of 10, Exceptional, (28)
"The A-frame cottage was clean and comfortable. I was accompanied by my son and two grandchildren (ages 12 and 14), and we really loved it. We went fishing in bay at the beach area below the cottage, and also did a lot of fossil hunting along the cliffs, which are breathtaking. Our host Teresa was extremely helpful and welcoming. We will definitely be going back!"
The price is £194
includes taxes & fees
30 Jun - 1 Jul
Soul Oasis - home on the Chesapeake Bay
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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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?

New! Cozy River Cottage with great views of the water!: This highly rated holiday home rental in St. Leonard is located on a river, and has a garden, 1 hot tub and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave.

How many holiday rentals are there in St. Leonard?

With 14 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 Patuxent River are a couple of lovely local spots to get outside and enjoy nature. Other places in town to visit include Jefferson Patterson Park and Museum and Flag Harbor Marina.

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.