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Leonardtown Vacation Rentals

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Check prices for these dates

In two weeks
Oct 17 - Oct 19
In two months
Nov 28 - Nov 30
In three months
Dec 26 - Dec 28
In four months
Jan 23 - Jan 25

Vacation Rentals in Leonardtown

Cheery, Peaceful Water Front Cabin on Winery Grounds
TV, fireplace, DVD player, books

Cheery, Peaceful Water Front Cabin on Winery Grounds

9.8 out of 10, Exceptional, (53)
"Great stay and peaceful spot. "
The price is ￥11,128
￥31,325 total
includes taxes & fees
Oct 7 - Oct 8
Cheery, Peaceful Water Front Cabin on Winery Grounds
Tiny, Funky, and Full of Love - Welcome to the Love Shack
Terrace/patio

Tiny, Funky, and Full of Love - Welcome to the Love Shack

9.8 out of 10, Exceptional, (8)
Tiny, Funky, and Full of Love - Welcome to the Love Shack
Waterfront with spectacular view, close to restaurants and bars
Interior

Waterfront with spectacular view, close to restaurants and bars

9.8 out of 10, Exceptional, (53)
"We enjoyed our stay here! The place was incredibly clean and the view was perfect! "
Waterfront with spectacular view, close to restaurants and bars
Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay
Dining

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

10.0 out of 10, Exceptional, (179)
"Cottage was just as pictured. Lots of character and charm. Host, Brett was easy to work with and very helpful!"
Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay
Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing
Property grounds

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

9.8 out of 10, Exceptional, (151)
"The place was great, the host was great,"
Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing
FAMILY FRIENDLY CREEKSIDE GETAWAY - HIDEAWAY AND ENJOY THE FAMILY MOMENTS
Fridge, microwave, oven, stovetop

FAMILY FRIENDLY CREEKSIDE GETAWAY - HIDEAWAY AND ENJOY THE FAMILY MOMENTS

10.0 out of 10, Exceptional, (193)
"Great for our group of 2 families. Plenty of beds, nice gathering space, access to the creek, played in the grassy field. Would/will likely return! "
FAMILY FRIENDLY CREEKSIDE GETAWAY - HIDEAWAY AND ENJOY THE FAMILY MOMENTS
A Hideaway in Hays Beach: Chesapeake Bay, 5G WiFi, 60 Second Walk to Beach
Fridge, microwave, oven, stovetop

A Hideaway in Hays Beach: Chesapeake Bay, 5G WiFi, 60 Second Walk to Beach

10.0 out of 10, Exceptional, (123)
"Really enjoyed our time here. The outdoor space in the back was great with the swing and the fire pits. Our kids loved walking to the beach everyday and catching crabs. "
A Hideaway in Hays Beach: Chesapeake Bay, 5G WiFi, 60 Second Walk to Beach
El Camino
Terrace/patio

El Camino

10.0 out of 10, Exceptional, (49)
"Great location, the dock is perfect for sunsets, nice balance of waterfront but also cabin vibes"
El Camino
Waterfront Loft on the Yeocomico River - Kayaks, Dock & Screened Porch
Exterior

Waterfront Loft on the Yeocomico River - Kayaks, Dock & Screened Porch

10.0 out of 10, Exceptional, (3)
"Our stay was absolutely perfect. It was just what we needed a place by the water saturated with nature and wildlife. It was the perfect quiet getaway, Bill and Caren are wonderful host filled with plenty of hospitality. Thank you."
Waterfront Loft on the Yeocomico River - Kayaks, Dock & Screened Porch
Bay view from Calvert Cliffs, Solomons Island & State Park nearby
Smart TV, fireplace

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

10.0 out of 10, Exceptional, (55)
"Such a beautiful place to stay. Had absolutely everything you could need. Comfy beds and tons of space. Definitely recommend staying here!"
Bay view from Calvert Cliffs, Solomons Island & State Park nearby
Waterfront Solomons Apartment
Interior

Waterfront Solomons Apartment

9.2 out of 10, Wonderful, (12)
"Very clean, awesome location and amazing hosts!! "
The price is ￥17,918
￥37,282 total
includes taxes & fees
Oct 8 - Oct 9
Waterfront Solomons Apartment
Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp
Exterior

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

9.8 out of 10, Exceptional, (75)
"What a great property, wildlife abounds!!! We had a fantastic weekend with family and friends!"
Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp
Cozy Cottage with access to and partially obstructed views of the bay.
Fridge, microwave, oven, stovetop

Cozy Cottage with access to and partially obstructed views of the bay.

9.0 out of 10, Wonderful, (29)
"Property was cozy and clean. Owners left lights on for us knowing we had a late arrival. Would definitely stay again. "
Cozy Cottage with access to and partially obstructed views of the bay.
Waterfront Wildlife Retreat on the Patuxent River
Interior

Waterfront Wildlife Retreat on the Patuxent River

10.0 out of 10, Exceptional, (171)
"We went here just for a little weekend getaway for my boyfriend, his brother, his brother’s girlfriend and their kids. We had the absolute best time, such a nice getaway even if it was only for 3 days. The view of the bay from the house is gorgeous and everything was perfect. I will be recommending this stay to anyone I can! "
Waterfront Wildlife Retreat on the Patuxent River
Waterfront Cottage with Pier & Boatlift on the Beautiful Potomac River
Property grounds

Waterfront Cottage with Pier & Boatlift on the Beautiful Potomac River

10.0 out of 10, Exceptional, (18)
"Great place! "
Waterfront Cottage with Pier & Boatlift on the Beautiful Potomac River
Waterfront Cottage in Beautiful Hoopers Island
Property grounds

Waterfront Cottage in Beautiful Hoopers Island

10.0 out of 10, Exceptional, (79)
"We had a very nice stay and enjoyed the quiet environment and the amenities of the property. Lots of great area for walking. "
Waterfront Cottage in Beautiful Hoopers Island
Secluded Riverfront Retreat on 100+ Acre Farm in Mechanicsville, WiFi, AC, &More
Smart TV, printers

Secluded Riverfront Retreat on 100+ Acre Farm in Mechanicsville, WiFi, AC, &More

10.0 out of 10, Exceptional, (3)
"My first thought was "gorgeous", when i walked through the door. This was just the weekend I needed. The screened in porch was relaxing. Be ready to take pictures of the sunrise! "
Secluded Riverfront Retreat on 100+ Acre Farm in Mechanicsville, WiFi, AC, &More
Beachfront Hideaway - Pet Friendly, Hot Tub, EV
Dining

Beachfront Hideaway - Pet Friendly, Hot Tub, EV

9.6 out of 10, Exceptional, (10)
"This was a great place for a December get-away. The location was lovely, and well stocked, with a full kitchen for those who like to cook, herbs, spices, condiments, cleaning supplies, fluffy bathrobes, q-tips, laundry detergent, etc. We needed to communicate wtih the owners a few times, and they were a pleasure to talk to. We decided to spend a little more on our get-away, and it was totally worth it. "
Beachfront Hideaway - Pet Friendly, Hot Tub, EV
Waterfront Sunsets, Fishing, Boating, and Crabs! Paxs River, Budds Creek MIR.
Property grounds

Waterfront Sunsets, Fishing, Boating, and Crabs! Paxs River, Budds Creek MIR.

10.0 out of 10, Exceptional, (14)
"Everything we needed, relaxing visit"
Waterfront Sunsets, Fishing, Boating, and Crabs! Paxs River, Budds Creek MIR.
Modern 3-bedroom house in Colonial Beach with access to pool and private hot tub
Interior

Modern 3-bedroom house in Colonial Beach with access to pool and private hot tub

10.0 out of 10, Exceptional, (7)
"It was an absolute delight staying at this Colonial Beach rental! From the moment we arrived, we were charmed by its cozy and inviting atmosphere. The house was clean, beautifully decorated, and had everything we needed for a comfortable and relaxing getaway."
Modern 3-bedroom house in Colonial Beach with access to pool and private hot tub
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 Leonardtown Hotel Reviews

Island Inn & Suites, an Ascend Collection Hotel

Island Inn & Suites, an Ascend Collection Hotel

10/10 Excellent
"Great balcony view overlooking Potomac River!"
jerry 4-night trip
Posted 4 days ago
Island Inn & Suites, an Ascend Collection Hotel

Find out more about Leonardtown

Find out more about Leonardtown

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

  • View our selection of featured holiday rentals in Leonardtown
  • Use the map to find apartments and other holiday homes in the Leonardtown neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Leonardtown while they last

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

Frequently asked questions

Are there vacation rentals in Leonardtown?

Yes, there are vacation rentals in Leonardtown near Saint Mary's Fairground, or you can choose a more secluded option if you're looking for extra privacy while you relax. Leonardtown is known for its seafood restaurants and festivals. Make sure you have time to check out the sporting events while you're in the area.

What are some of the best vacation rentals that Leonardtown has to offer?

Waterfront with spectacular view, close to restaurants and bars: This vacation home rental near Leonardtown is located on a river and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. You and your friends and family can relax into your vacation with amenities like a selection of books.

How many vacation rentals will I find in Leonardtown?

With 11 Expedia vacation rentals, you're sure to find just the right place for your Leonardtown stay.

What’s there to see and do in Leonardtown?

St. Mary's River State Park and Leonardtown Park are a couple of lovely local spots to get outside and enjoy nature. While here, Port of Leonardtown Winery and Leonardtown Town Hall are other places worth a visit.

What’s a vacation rental in Leonardtown like?

Vacation rentals are privately owned properties you can stay in for a few weeks or just a few days in Leonardtown. Vacation rentals offer extras such as WiFi and washers and dryers so you'll be comfy for your stay. If you're concerned about a sanitized environment, a vacation rental can offer a sense of privacy away from public hotel elevators and busy front desks while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a great option for a family trip.