St. Leonard Holiday Rentals

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Check prices for these dates

In two weeks
31 Oct - 2 Nov
In one month
14 Nov - 16 Nov
In two months
12 Dec - 14 Dec
In three months
9 Jan - 11 Jan

Holiday Rentals in St. Leonard

On the beach
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.
9.6 out of 10, Exceptional, (5)
"Just the perfect place I needed for a personal retreat. It is quiet, peaceful and serene. I would definitely visit again. "
The price is HK$1,399
HK$2,327 total
includes taxes & fees
17 Oct - 18 Oct
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Sun-loungers, beach towels
Soul Oasis - home on the Chesapeake Bay
Soul Oasis - home on the Chesapeake Bay
9.8 out of 10, Exceptional, (35)
"Lovely house with tons of character. Clean and comfortable. A few steps from water. "
The price is HK$1,166
HK$2,423 total
includes taxes & fees
20 Oct - 21 Oct
Soul Oasis - home on the Chesapeake Bay
Fridge, microwave, oven, stovetop
Riverside Dreams -golfcart-views-screened porch-
Riverside Dreams -golfcart-views-screened porch-
2.0 star property
10.0 out of 10, Exceptional, (3)
"We found the view and the accommodations quite lovely."
The price is HK$816
HK$2,987 total
includes taxes & fees
19 Oct - 20 Oct
Riverside Dreams -golfcart-views-screened porch-
Sun-loungers
Cottage Located on the Patuxent River!
Cottage Located on the Patuxent River!
10.0 out of 10, Exceptional, (42)
"The accommodations were superb and being on the water was amazing!"
The price is HK$2,293
HK$2,744 total
includes taxes & fees
1 Nov - 2 Nov
Cottage Located on the Patuxent River!
Interior
Waterfront Solomons Apartment
Waterfront Solomons Apartment
9.2 out of 10, Wonderful, (13)
"Very clean, awesome location and amazing hosts!! "
The price is HK$1,005
HK$2,013 total
includes taxes & fees
18 Oct - 19 Oct
Waterfront Solomons Apartment
Interior
Charming 2-bedroom 1 bath cottage with AC, WiFi in peaceful North Beach, Md.
Charming 2-bedroom 1 bath cottage with AC, WiFi in peaceful North Beach, Md.
2.0 star property
The price is HK$1,001
HK$2,157 total
includes taxes & fees
3 Nov - 4 Nov
Charming 2-bedroom 1 bath cottage with AC, WiFi in peaceful North Beach, Md.
Interior
Beautiful Waterfront Retreat in Cambridge!
Beautiful Waterfront Retreat in Cambridge!
10.0 out of 10, Exceptional, (47)
"Property was as listed. We enjoyed are stay."
The price is HK$1,399
HK$3,057 total
includes taxes & fees
22 Oct - 23 Oct
Beautiful Waterfront Retreat in Cambridge!
Beach nearby
Walk to Beach! King Bed & Free Beach Passes
Walk to Beach! King Bed & Free Beach Passes
10.0 out of 10, Exceptional, (16)
"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!"
The price is HK$999
HK$2,942 total
includes taxes & fees
20 Oct - 21 Oct
Walk to Beach! King Bed & Free Beach Passes
Outdoor dining
The Hidaway on the Patuxent River<br>Children allowed and welcomed to stay.
The Hidaway on the Patuxent River<br>Children allowed and welcomed to stay.
9.2 out of 10, Wonderful, (9)
"Got to go fishing, kayaking, and swimming in the pool. Had a great time, views are wonderful and it’s a peaceful environment. 10/10 would stay again."
The price is HK$2,099
HK$4,285 total
includes taxes & fees
17 Oct - 18 Oct
The Hidaway on the Patuxent River<br>Children allowed and welcomed to stay.
Terrace/patio
Waterfront Escape | Family-Friendly | Remodeled Home | Epic Sunset Views | Decks
Waterfront Escape | Family-Friendly | Remodeled Home | Epic Sunset Views | Decks
10.0 out of 10, Exceptional, (3)
"Everything was very clean and well put together. Loved the view!"
The price is HK$1,306
HK$2,933 total
includes taxes & fees
20 Oct - 21 Oct
Waterfront Escape | Family-Friendly | Remodeled Home | Epic Sunset Views | Decks
Sun-loungers, beach towels
Modern Waterfront Home with Kayak, Firepit, Gameroom, Pool+Beaches, Dog & EV OK
Modern Waterfront Home with Kayak, Firepit, Gameroom, Pool+Beaches, Dog & EV OK
10.0 out of 10, Exceptional, (4)
"They thought of everything. I would definitely come back for another stay."
The price is HK$1,551
HK$3,422 total
includes taxes & fees
21 Oct - 22 Oct
Modern Waterfront Home with Kayak, Firepit, Gameroom, Pool+Beaches, Dog & EV OK
Fridge, microwave, stovetop, coffee/tea maker
Cozy centrally located studio with WiFi and AC in peaceful Port Republic, MD
Cozy centrally located studio with WiFi and AC in peaceful Port Republic, MD
9.4 out of 10, Exceptional, (6)
"Great place to stay"
The price is HK$591
HK$1,338 total
includes taxes & fees
29 Oct - 30 Oct
Cozy centrally located studio with WiFi and AC in peaceful Port Republic, MD
Beach nearby, sun-loungers, beach towels
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
10.0 out of 10, Exceptional, (30)
"Absolutely beautiful and spacious home perfectly located in North Beach. Very peaceful area and close to the beach, restaurants and shopping. We really enjoyed our stay and hope to visit again in the future. "
The price is HK$1,385
HK$3,893 total
includes taxes & fees
19 Oct - 20 Oct
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
Fridge, microwave, oven, stovetop
Tranquil Modern Farmhouse
Tranquil Modern Farmhouse
9.4 out of 10, Exceptional, (6)
"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! "
The price is HK$1,749
HK$4,112 total
includes taxes & fees
28 Oct - 29 Oct
Tranquil Modern Farmhouse
Fridge, microwave, oven, stovetop
Waterfront Getaway with Dock
Waterfront Getaway with Dock
10.0 out of 10, Exceptional, (51)
"Great location with everything you may need. It is close to restaurants and Emily’s produce.2nd time staying and will be back again. "
The price is HK$1,788
HK$2,093 total
includes taxes & fees
28 Oct - 29 Oct
Waterfront Getaway with Dock
Pool
Beach Front, Bay View, Fishing, chesapeake,Family Getaway
Beach Front, Bay View, Fishing, chesapeake,Family Getaway
9.0 out of 10, Wonderful, (6)
"Everything was great. The owner was extremely helpful. Couldn't ask for anything better."
The price is HK$1,539
HK$3,709 total
includes taxes & fees
16 Nov - 17 Nov
Beach Front, Bay View, Fishing, chesapeake,Family Getaway
3 bedrooms, iron/ironing board, travel cot, free WiFi
Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.
Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.
9.4 out of 10, Exceptional, (3)
"We had a short stay after a sporting event in DC, it was a little less than an hour away. Convenient location and a very clean house. Kitchen was well stocked. There was little communication with the owner, which was nice vs a long list of rules, but we would have liked to know any of their local specific favorite spots or more detailed check in/check out. Worked out nicely for our family. "
The price is HK$1,703
HK$3,197 total
includes taxes & fees
3 Nov - 4 Nov
Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.
Smart TV
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
10.0 out of 10, Exceptional, (14)
"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 "
The price is HK$2,394
HK$4,449 total
includes taxes & fees
20 Oct - 21 Oct
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
Beach
2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!
2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!
10.0 out of 10, Exceptional, (7)
"Clean and easy "
The price is HK$1,432
HK$2,878 total
includes taxes & fees
26 Oct - 27 Oct
2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!
TV, fireplace, ping pong
Anne & Fred`s Leonardtown Home W/ Arcade room!
Anne & Fred`s Leonardtown Home W/ Arcade room!
9.2 out of 10, Wonderful, (5)
"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."
The price is HK$1,944
HK$4,182 total
includes taxes & fees
19 Oct - 20 Oct
Anne & Fred`s Leonardtown Home W/ Arcade room!
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

Comfort Inn & Suites

Comfort Inn & Suites

10/10 Excellent
"everything was great"
Brent S 2-night trip
Posted 3 days ago
Comfort Inn & Suites

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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  • Enter your travel dates to view the best deals on holiday rentals in St. Leonard while they last

Look no further and take a look at our great range of rental properties in St. Leonard!

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?

Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub: This holiday home rental outside of St. Leonard is located on the waterfront, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a balcony, a garden and 1 hot tub so that you can immerse yourself in your holiday.

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 Jefferson Patterson Park and Museum and Patuxent River.

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.