St. Leonard holiday rentals

We found 133 holiday rentals — enter your dates for availability
Discover a selection of 20 homes and other holiday rentals in St. Leonard that are perfect for your trip. Whether you're travelling with a group or just with your pet, holiday homes have the best amenities for spending time at your holiday home, including parking and a TV. You'll be sure to find a property to rent that has what everyone needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts – St. Leonard

Showing deals for:25 Dec - 1 Jan

Dining
Property grounds
Exterior
Marina
Exceptional
(9 reviews)

Houseboat on Solomons Island

Solomons

8% off
AU$3,186
for 7 nights, 1 houseboat
AU$455 per night
includes taxes & fees
Houseboat on Solomons Island
Exterior
Dining
Living area
Games room
Exceptional
(5 reviews)

Beach House w/TheaterRm, GameRm, Outdoor Shwr

Lusby

8% off
AU$6,787
for 7 nights, 1 home
AU$970 per night
includes taxes & fees
Beach House w/TheaterRm, GameRm, Outdoor Shwr
Interior
Property grounds
Miscellaneous
Room
Wonderful
(15 reviews)

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

Benedict

8% off
AU$2,268
for 7 nights, 1 cottage
AU$324 per night
includes taxes & fees
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Property grounds
Exterior
Property grounds
Living area
Wonderful
(17 reviews)

Magnificent Water Front Property

Solomons

7% off
AU$8,125
for 7 nights, 1 home
AU$1,161 per night
includes taxes & fees
Magnificent Water Front Property
Property grounds
Outdoor dining
Living area
Terrace/patio
Exceptional
(11 reviews)

Bayview Cottage 2 BR +Off./Priv Beach/Hot Tub/Deck

Huntingtown

8% off
AU$5,128
for 7 nights, 1 cottage
AU$733 per night
includes taxes & fees
Bayview Cottage 2 BR +Off./Priv Beach/Hot Tub/Deck
Exterior
entryway
dining area
steps to the loft
Exceptional
(63 reviews)

Soul Oasis - home on the Chesapeake Bay

Lusby

8% off
AU$1,852
for 7 nights, 1 cottage
AU$265 per night
includes taxes & fees
Soul Oasis - home on the Chesapeake Bay
Private kitchen
Room
Living area
Interior
Exceptional
(17 reviews)

Bay Charm. 2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil!

Prince Frederick

8% off
AU$3,345
for 7 nights, 1 home
AU$478 per night
includes taxes & fees
Bay Charm. 2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil!
Exterior
Outdoor dining
Exterior detail
Outdoor dining
Exceptional
(174 reviews)

Harbor Cottage at the Chesapeake Bay - Dog Friendly Beach

St. Leonard

6% off
AU$2,126
for 7 nights, 1 cottage
AU$304 per night
includes taxes & fees
Harbor Cottage at the Chesapeake Bay - Dog Friendly Beach
Private kitchen
Hilltop cottage December
Wiew out east side windows
Open floor plan, dining table and sleep sofa
Exceptional
(30 reviews)

Quiet Woodland cottage near St. Leonard's Creek

Lusby

8% off
AU$1,151
for 7 nights, 1 cottage
AU$164 per night
includes taxes & fees
Quiet Woodland cottage near St. Leonard's Creek
Side view
Coffee, tea, cream, and sugar provided
Stairs leading to bedrooms
Living room
Exceptional
(16 reviews)

Two bedroom two bath home on charming Solomons Island

Solomons

8% off
AU$3,420
for 7 nights, 1 apartment
AU$489 per night
includes taxes & fees
Two bedroom two bath home on charming Solomons Island
Room
Living area
Private kitchen
Exterior detail
Exceptional
(31 reviews)

Studio on the Bay.

St. Leonard

8% off
AU$1,714
for 7 nights, 1 apartment
AU$245 per night
includes taxes & fees
Studio on the Bay.

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Find the perfect holiday rental for your St. Leonard getaway

The area's wineries and museums are just some of the reasons to come on holiday to St. Leonard. This city's shopping, sporting events and restaurants draw many visitors. Are you looking for specific amenities for your getaway? Many of our holiday rentals feature full kitchens and laundry facilities.

Activities and attractions in St. Leonard

Are you looking for top things to see and do during your stay? Venture out of your cosy holiday rental and check out everything that makes St. Leonard a fun place to get away to. These are some of the top attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Running Hare Vineyard (6.7 mi / 10.8 km)
  • Chesapeake Beach Water Park (15.1 mi / 24.3 km)
  • Breton Bay Golf Course (16.7 mi / 26.8 km)
  • Maryland International Raceway (18.3 mi / 29.5 km)
  • Budds Creek Motocross Park (18.5 mi / 29.7 km)
  • Michael P. O'Brien Athletics and Recreation Center (20.2 mi / 32.5 km)

Exploring the natural landscape of St. Leonard

Whether you're looking for fun outdoor activities or just want to appreciate the scenery, St. Leonard is a great place to get outside. These are some of the area's most enchanting features, all within 30 miles (48.2 km) of the city centre:

  • Matoaka Beach (1.5 mi / 2.4 km)
  • Flag Ponds Nature Park (2.9 mi / 4.6 km)
  • Cove Point Beach (9.1 mi / 14.7 km)
  • Breezy Point Beach (10.1 mi / 16.3 km)
  • St. Mary's River State Park (14.9 mi / 24 km)
  • Elms Beach Park (20.6 mi / 33.2 km)

Transport to and around St. Leonard

The nearest airport is in Ronald Reagan National Airport (DCA), located 38.8 mi (62.4 km) from the city centre.

Frequently asked questions

What is the best area to stay in St Leonard when booking a holiday rental?
When considering a holiday rental in St Leonard, Maryland, the nearby area of Solomons is an excellent choice. This charming waterfront community offers a delightful blend of relaxation and recreational activities. Visitors can enjoy the stunning views of the Patuxent River and explore attractions such as the Calvert Marine Museum, which showcases the region's maritime heritage, and the iconic Drum Point Lighthouse, a picturesque spot great for photography enthusiasts.Another appealing area is Chesapeake Beach, known for its vibrant boardwalk and family-friendly atmosphere. Here, you can indulge in fresh seafood at local eateries and enjoy the sandy beaches along the Chesapeake Bay. This area typically features a variety of rental properties, providing options to suit different group sizes and budgets.
Where are the best areas for renting a beach house in St Leonard?
For renting a beach house in St Leonard, Maryland, the area around the Chesapeake Bay offers picturesque settings and a tranquil atmosphere. The waterfront locations near the St. Leonard Creek provide access to beautiful sandy beaches and calm waters, ideal for families looking to enjoy various water activities such as swimming, kayaking, and fishing. Many holiday rentals in this region feature amenities like private docks, outdoor seating areas, and spacious decks great for entertaining or relaxing while enjoying bay views.In addition, properties within the nearby Calvert Cliffs State Park offer the opportunity for nature enthusiasts to explore scenic trails and fossil hunting along the cliffs. Accommodations here often come equipped with modern conveniences such as fully stocked kitchens and outdoor grills, enabling guests to enjoy home-cooked meals after a day of adventure.Furthermore, the local community boasts quaint shops and eateries, ensuring that visitors have access to fresh seafood and local produce, enhancing the coastal living experience.
What is the most popular type of holiday rental accomodation in St Leonard?
In St Leonard, holiday houses are the most popular type of holiday rental, with about 42 available throughout the area. These homes typically feature spacious layouts with multiple bedrooms, fully equipped kitchens, and outdoor areas, great for families or groups looking to enjoy the nearby Chesapeake Bay. Additionally, there are around 12 cottages that offer a charming, rustic feel, often equipped with amenities like fireplaces and porches for relaxed outdoor living. While there are several apartments as well, they tend to be less common compared to the larger holiday houses and cottages.
Are there any family house rentals in St Leonard?
In St Leonard, Maryland, there are numerous family-friendly rentals available, with around 15 options to choose from. This charming area is great for families, offering spacious homes equipped with essential amenities such as full kitchens, comfortable living rooms, and outdoor spaces for children to enjoy. Many properties also feature private patios or decks, ideal for relaxation after a day of exploring.Visitors can take advantage of the nearby attractions, including the scenic beaches of the Patuxent River and the natural beauty of the surrounding parks. Families looking to enjoy outdoor activities will find opportunities for hiking, fishing, and picnicking close by.
Can I rent a holiday home with a pool or hot tub in St Leonard?
In St Leonard, Maryland, there are several holiday homes available for rent that feature pools and hot tubs. This serene area, located along the Patuxent River, offers a lovely setting for relaxation and recreation. Many of the properties come equipped with private pools, inviting hot tubs, and outdoor spaces superb for enjoying the pleasant weather. Additionally, travellers can expect amenities such as fully equipped kitchens for self-catering, spacious living areas, and sometimes even access to waterfront activities.
Are there pet-friendly house rentals in St Leonard?
In St Leonard, Maryland, there are several pet-friendly holiday house rentals available for those looking to enjoy a getaway with their furry companions. Many of these properties come equipped with amenities such as spacious yards, private decks, and fully equipped kitchens, making them suitable for families or groups.The area is known for its proximity to the beautiful Patuxent River, where you can enjoy various outdoor activities, including fishing and kayaking. Additionally, St Leonard is close to parks and nature reserves that welcome pets, providing ample opportunities for walks and exploration. The charming community offers a relaxed atmosphere, superb for unwinding after a day of adventure.
Are there any remote work holiday rentals in St Leonard?
In St Leonard, Maryland, there are numerous remote work holiday rentals available, with around 60 options to choose from. This charming area offers a tranquil environment for remote workers, with many properties equipped with essential amenities such as free Wi-Fi, dedicated workspaces including desks and computer monitors, and comfortable chairs to ensure productivity.The town is located near the scenic waters of the Chesapeake Bay, providing opportunities for outdoor activities during breaks, such as kayaking or enjoying peaceful walks along the waterfront. St Leonard also offers a friendly community atmosphere, with local shops and restaurants adding convenience for extended stays. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in St Leonard?
In St Leonard, popular rental amenities typically include a fully equipped kitchen, allowing guests to prepare their own meals. Many properties feature a deck or patio, great for enjoying the outdoors and relaxing after a day of exploring. Additionally, travellers can expect conveniences such as onsite parking, making it easy to bring a vehicle. A coffee and tea maker is also commonly found in these rentals, ensuring guests can enjoy a warm beverage at their leisure.
When is the best time to visit St Leonard for a holiday rental?
The best time to visit St Leonard for a holiday rental is during the peak season from July to September. This is when the area comes alive with activity, superb for families and outdoor enthusiasts seeking a delightful getaway. Visitors can enjoy beautiful weather, with temperatures typically ranging from 20 to 30 degrees Celsius, making it ideal for beach outings, kayaking, and exploring the scenic Patuxent River.July stands out as the most popular month, bringing vibrant community events and festivals that enhance the local charm. Whether you're lounging on the sandy shores or engaging in water sports, there's a palpable energy to the atmosphere that many travellers find irresistible.For those looking for a more budget-friendly option, consider visiting in November. This month offers a quieter experience, superb for leisurely walks along the waterfront and enjoying the peacefulness of the area without the bustling crowds. The fall foliage adds a beautiful touch to the landscape, making it a lovely time for nature lovers.Ultimately, your choice depends on whether you prefer the lively summer scene filled with activities or the tranquil beauty of the fall.
What are the top attractions in St Leonard?
In St Leonard, Maryland, visitors can enjoy a blend of natural beauty and historical sites. The Calvert Marine Museum is a key attraction, showcasing the rich maritime history of the region and offering engaging exhibits for all ages. Nearby, the picturesque Chesapeake Bay provides opportunities for boating, fishing, and enjoying scenic waterfront views.For those interested in outdoor activities, the nearby Flag Ponds Nature Park offers hiking trails, beaches, and chances to observe local wildlife, making it a great spot for nature enthusiasts. The area is also known for its charming small-town atmosphere, with local shops and eateries that reflect the community's character.
Are all fees included in the St. Leonard holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any St. Leonard holiday homes with parking?
Stayz offers a wide selection of holiday homes in St. Leonard with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for St. Leonard holiday homes?
You can find great discounts on holiday homes in St. Leonard on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my St. Leonard holiday home booking on Stayz?
To find St. Leonard holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in St. Leonard?
A long-stay holiday home in St. Leonard is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a St. Leonard holiday home?
Book your St. Leonard holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in St. Leonard?
Prices for holiday homes in St. Leonard vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in St. Leonard to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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