St. Leonard Vacation Rentals

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Check prices for these dates

In two weeks
May 29 - May 31
In two months
Jul 10 - Jul 12
In three months
Aug 7 - Aug 9
In four months
Sep 4 - Sep 6

Our top choices for St. Leonard vacation rentals

Beach nearby

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)
"Although the house itself could use some maintenance, our stay was very comfortable. The rooms were spacious and it had all the amenities we needed. "
United States
Donovan B.
The price is ￥10,930
￥48,405 total
includes taxes & fees
May 14 - May 15
Walk to Beach! King Bed & Free Beach Passes
House (3 Bedrooms) | Interior

Lakefront Log Cabin Retreat w/ Hot tub + Kayaks!

Lakefront Log Cabin Retreat w/ Hot tub + Kayaks!
3.0 star property
Lusby
The price is ￥66,902
￥153,298 total
includes taxes & fees
May 13 - May 14
Lakefront Log Cabin Retreat w/ Hot tub + Kayaks!
Cottage, 2 Bedrooms, Kitchen | Exterior

Coles Point Marina

Coles Point Marina
2.0 star property
Hague
The price is ￥36,601
￥54,312 total
includes taxes & fees
Jun 8 - Jun 9
Coles Point Marina
Exterior

Soul Oasis - home on the Chesapeake Bay

Soul Oasis - home on the Chesapeake Bay
Lusby
10.0 out of 10, Exceptional, (46 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 ￥21,622
￥47,167 total
includes taxes & fees
May 20 - May 21
Soul Oasis - home on the Chesapeake Bay
Private kitchen

3-Bedroom Beach Home w/ Backyard

3-Bedroom Beach Home w/ Backyard
North Beach
The price is ￥30,459
￥67,766 total
includes taxes & fees
May 13 - May 14
3-Bedroom Beach Home w/ Backyard
Smart TV

WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
Cambridge
10.0 out of 10, Exceptional, (14 reviews)
"Second time staying at this lovely, serene home/property. It’s the perfect getaway if you’re looking to escape into some peace! Highly recommend "
United States
Jill C.
The price is ￥50,102
￥93,965 total
includes taxes & fees
May 20 - May 21
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
Property grounds

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 ￥23,972
￥41,694 total
includes taxes & fees
May 13 - May 14
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Interior

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 ￥32,433
￥55,637 total
includes taxes & fees
May 13 - May 14
Bright and airy waterfront getaway
Exterior

2 Bedroom Cottage at Coles Point Marina

2 Bedroom Cottage at Coles Point Marina
Hague
The price is ￥54,055
￥66,314 total
includes taxes & fees
May 13 - May 14
2 Bedroom Cottage at Coles Point Marina
Sun loungers

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 ￥47,239
￥54,391 total
includes taxes & fees
May 20 - May 21
Cottage Located on the Patuxent River!
Property grounds

Come relax yourself a while

Come relax yourself a while
Mechanicsville
The price is ￥38,778
￥91,966 total
includes taxes & fees
May 13 - May 14
Come relax yourself a while
Smart TV, books

Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.

Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.
Prince Frederick
9.8 out of 10, Exceptional, (6 reviews)
"Our family had a great stay. Thank you!"
United States
Colleen G.
The price is ￥36,036
￥71,248 total
includes taxes & fees
May 20 - May 21
Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.
Exterior

Charming Waterfront 3-bedroom house in Piney Point

Charming Waterfront 3-bedroom house in Piney Point
Piney Point
10.0 out of 10, Exceptional, (2 reviews)
"Beautifully and tastefully decorated, immaculately clean, completely stocked top to bottom! You can tell by all of the details that these hosts care about curating a perfect stay for their guests. "
United States
Leslie K.
The price is ￥48,257
￥92,392 total
includes taxes & fees
May 13 - May 14
Charming Waterfront 3-bedroom house in Piney Point
Pool

Family Beach House: Spacious Deck, Grill & Views

Family Beach House: Spacious Deck, Grill & Views
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 ￥27,508
￥77,424 total
includes taxes & fees
May 19 - May 20
Family Beach House: Spacious Deck, Grill & Views
Fridge, microwave, oven, stovetop

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 ￥36,036
￥43,513 total
includes taxes & fees
May 20 - May 21
Waterfront Getaway with Dock
Dining

Beach House w/TheaterRm, GameRm, Outdoor Shwr

Beach House w/TheaterRm, GameRm, Outdoor Shwr
Lusby
10.0 out of 10, Exceptional, (2 reviews)
"This was a fantastic property and location for our stay in Lusby. The home is designed with families in mind, and there was plenty for everyone to do. The house is beautiful and in a quiet, residential community. You can walk to the beach less than two blocks away, and we found dozens of sharks teeth there! Josh was so helpful with advice throughout. We would definitely come again."
United States
Mollie O.
The price is ￥51,017
￥114,034 total
includes taxes & fees
May 18 - May 19
Beach House w/TheaterRm, GameRm, Outdoor Shwr
Outdoor dining

Sunset Breezes - quiet waterfront retreat

Sunset Breezes - quiet waterfront retreat
Dorchester County
10.0 out of 10, Exceptional, (44 reviews)
"The place was vey clean, whic is of upmost improtance to me. We loved the veiw and the location."
United States
Crystal H.
The price is ￥55,621
￥70,209 total
includes taxes & fees
May 27 - May 28
Sunset Breezes - quiet waterfront retreat
Interior

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, (8 reviews)
"Everything was very clean and well put together. Loved the view!"
United States
Minji S.
The price is ￥28,986
￥61,861 total
includes taxes & fees
May 18 - May 19
Waterfront Retreat, Private Pier, Remodeled, Epic Views, Sunsets on the River
TV, fireplace, video games, books

Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock

Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock
Lusby
10.0 out of 10, Exceptional, (1 review)
"We loved our stay! Lovely home, beautiful view"
United States
Sarah R.
The price is ￥75,833
￥157,272 total
includes taxes & fees
May 13 - May 14
Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock
Smart TV, fireplace, computer monitors, printers

Tranquil Modern Farmhouse

Tranquil Modern Farmhouse
Waldorf
9.0 out of 10, Wonderful, (8 reviews)
"This property was super gorgeous and spacious so we were able to relax. Guests had more than enough space and didn’t feel like they were on top of each other sleeping wise! We were able to just have dinner and feel safe! The owner answered any questions we had within 15 minutes, which was super helpful! "
United States
khaddija j.
The price is ￥58,661
￥112,186 total
includes taxes & fees
May 25 - May 26
Tranquil Modern Farmhouse
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

Island Inn & Suites, an Ascend Collection Hotel

Island Inn & Suites, an Ascend Collection Hotel

8/10 Good
"Nice stay, clean room, comfy bed, building very well maintained, plenty parking spaces. Beautiful sunset views from across the street. The only thing I didn’t like is the room we got was facing the parking lot with a view of the water blocked by a tree, we told the front desk about it, but weren’t offered to move even though the hotel wasn’t fully booked. Restaurant next door is a plus"
Flor 1-night trip
Posted 2 hours ago
Island Inn & Suites, an Ascend Collection Hotel

Find out more about St. Leonard

Search for holiday rentals in St. Leonard on Expedia! You can easily find your home rentals, villas, holiday apartments in St. Leonard using one of the methods below:

  • View our selection of featured holiday rentals in St. Leonard
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Look no further and take a look at our great range of rental properties in St. Leonard!

Frequently asked questions

Can I find a vacation rental in St. Leonard?

Yes, we offer vacation rentals close to the most popular points of interest in St. Leonard, or you can choose a more secluded option if you want a relaxing place to 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's the top vacation rental that St. Leonard has to offer?

The Blue Crab Beach House - Free beach passes : This vacation home rental near St. Leonard is located near the beach and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Kick off your shoes and enjoy yourself with a private yard and a selection of games.

How many vacation rentals are there in St. Leonard?

With 18 Expedia vacation rentals, you're sure 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 vacation rental in St. Leonard like?

Vacation rentals are privately owned properties you can book for a couple of days or more in St. Leonard. Vacation rentals feature extras like laundry facilities and kitchens to help you enjoy your stay. If you're concerned about a clean environment, a vacation rental can provide a sense of security away from shared hotel elevators and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a hotel, which makes a vacation rental a great option for a family trip or a small group gathering.