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Leonardtown Holiday Rentals

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Holiday Rentals in Leonardtown

Property grounds
Blue Heron Cottage is cozy & convenient. Renovated March 2023!
10.0 out of 10, Exceptional, (21)
"Perfect little cottage to enjoy all that is C beach. Fenced yard for the dog was a plus."
Blue Heron Cottage is cozy & convenient. Renovated March 2023!
Outdoor dining
The Schultz Estate
10.0 out of 10, Exceptional, (4)
"Had a great stay! Beautiful location! House was clean roomy, overall had a great time! The only thing I would say is work on the doors closing. In restrooms."
The Schultz Estate
Property grounds
Picture Perfect Waterfront in town Sleeps 6 Expansive Outdoor dining area
10.0 out of 10, Exceptional, (5)
"The house was clean and well appointed. The location was great for bike riding to restaurants and checking out the area. The views from the deck were awesome anytime of the day or night. Would stay again!"
Picture Perfect Waterfront in town Sleeps 6 Expansive Outdoor dining area
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Property grounds
Waterfront Cottage in Beautiful Hoopers Island
10.0 out of 10, Exceptional, (53)
"Had a wonderful time really enjoyed the use of the dock the house was perfect had everything you could of possibly needed definitely will be back!"
Waterfront Cottage in Beautiful Hoopers Island
Beach
Waterfront Relaxing Getaway
10.0 out of 10, Exceptional, (11)
"I was looking for a nice, quiet, and relaxing, vacation. This property did not disappoint. The house was comfortable, cozy, well stocked, and so clean. The view is incredible. Just sitting outside watching the river was so "Zen". I had one of the most restful vacations ever. I was there for a little over two weeks and I would have stayed longer if I could have, Kim, the host, was very friendly and helpful. I look forward to staying at this beautiful property again."
The price is NZ$686
per night
3 Jun - 4 Jun
Waterfront Relaxing Getaway
Beach
Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp
10.0 out of 10, Exceptional, (51)
"What a fantastic property! We loved staying here and our family had such a great time exploring. Sadly it was a drizzly, dreary weekend but we had one nice day to go down to the beach and the kids enjoyed playing in the water. We loved the variety of porches to sit on and have different views and there was plenty of room for the kids to play indoors when it was raining. Overall a great experience. Thank you!"
Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp
Beach nearby, sun-loungers, beach towels
Relax & Renew in a WATERFRONT Cottage , private pier, kayaks, fishing, wineries.
10.0 out of 10, Exceptional, (35)
"Perfect getaway.. Clean, cozy place with refreshing view! Ample amenities and accommodating host! Loved our stay and won’t hesitate to visit again!"
Relax & Renew in a WATERFRONT Cottage , private pier, kayaks, fishing, wineries.
Exterior
Soul Oasis - home on the Chesapeake Bay
10.0 out of 10, Exceptional, (6)
"Pleasant relaxing time. We were pleased and impress to locate this property"
The price is NZ$465
per night
22 May - 23 May
Soul Oasis - home on the Chesapeake Bay
Smart TV, fireplace
Bay view from Calvert Cliffs, Solomons Island & State Park nearby
10.0 out of 10, Exceptional, (28)
"The house was great and nice area!"
Bay view from Calvert Cliffs, Solomons Island & State Park nearby
Property grounds
Maryland Vacation Rental w/ Private Pool & Dock
10.0 out of 10, Exceptional, (4)
"Loved the house and kids loved the pool. We also managed to catch a half dozen crabs (August trip). House is on the smaller side, but with four bedrooms everyone had privacy and just what they needed. We'll be back!"
Maryland Vacation Rental w/ Private Pool & Dock
Fridge, microwave, oven, stovetop
Inviting and Serene Home on Monroe Bay Creek
10.0 out of 10, Exceptional, (39)
"Lovely place; well maintained and appointed. Very clean and charming neighbors. Would stay again. Only complaint is the electric stove (not induction); controlling temperature is challenging."
Inviting and Serene Home on Monroe Bay Creek
3 bedrooms, desk, iron/ironing board, free WiFi
Breathtaking Views, 450 pier, kayaks, fossils, priv beach, 45 min to D.C.
10.0 out of 10, Exceptional, (101)
"Really enjoyed our time there. Very relaxing. Comfortable home. All amenities there. Especially loved the windows..."
Breathtaking Views, 450 pier, kayaks, fossils, priv beach, 45 min to D.C.
Fridge, microwave, oven, stovetop
**FAMILY FRIENDLY CREEKSIDE GETAWAY - HIDEAWAY AND ENJOY THE FAMILY MOMENTS**
10.0 out of 10, Exceptional, (170)
"We spent the weekend relaxing in the outdoors with family. We kayaked, had an outdoor fire and enjoyed the wildlife that floated or flew by."
**FAMILY FRIENDLY CREEKSIDE GETAWAY - HIDEAWAY AND ENJOY THE FAMILY MOMENTS**
Fridge, microwave, oven, stovetop
Large Luxury 4 bed/3 bath Beach House-2 Blocks to beach, 1 Block to Bay
10.0 out of 10, Exceptional, (39)
"My daughter (age 21) and myself stayed at this home for the past few days. We had such a lovely time! The house is beautiful and Diana has thought of everything to make you feel welcome. The house has a wonderful layout and a comforting vibe. Out of all the vacations we have taken, we were the saddest to leave this place lol and we are already making our next plans to come back! I loved the little goodies Diana has for sale around the house that makes it convenient and also goes to a wonderful...
Large Luxury 4 bed/3 bath Beach House-2 Blocks to beach, 1 Block to Bay
Property grounds
Waterfront with spectacular view, close to restaurants and bars
10.0 out of 10, Exceptional, (21)
"This was our first time in Colonial Beach and we really enjoyed it. Definitely recommend renting a golf cart to get around town. The house is beautiful and in a great location close to everything. The homeowner was also great to work with and we’ll definitely be back soon!"
Waterfront with spectacular view, close to restaurants and bars
Exterior
Private Retreat Bungalow-One Level, 2 blocks from Beach w/Porch & Deck
10.0 out of 10, Exceptional, (26)
"It was the perfect spot to go work from for a bit to be near water and get out of the hustle and bustle of the DC area! Absolutely loved the house and the town! A hidden gem."
Private Retreat Bungalow-One Level, 2 blocks from Beach w/Porch & Deck
Fitness facility
Quiet Oasis for the Whole Fam, Relax On The Porch Or 1 Minute Walk to the Beach!
10.0 out of 10, Exceptional, (131)
"This home is perfect for multiple families to meet. Two bwdrooms on one aide of the house and another bedroom across the house all on the main floor. Two additional bwdrooms upstairs and three bathrooms. Everyone was comfortable and had privacy and the best part was the house was really quiet. We couldn't hear people walkaround above us. The wings are separated by a huge living room with couches, games, books and a huge dining table. Charming! There is a spectacular view of the water and the...
Quiet Oasis for the Whole Fam, Relax On The Porch Or 1 Minute Walk to the Beach!
Property grounds
The Beach Retreat is a cozy beach Villa with Hottub overlooking a private beach.
10.0 out of 10, Exceptional, (25)
"Our family had the BEST time at this beach house! Such a relaxing and enjoyable view. We just returned home, and I miss the tranquility already. Great communication with host and property was exactly as described. Clean, cozy and everything you could need and then some!"
The Beach Retreat is a cozy beach Villa with Hottub overlooking a private beach.
Beach
Belle of the Chesapeake Bay
10.0 out of 10, Exceptional, (2)
"The property was very clean and nicely appointed."
Belle of the Chesapeake Bay
TV, fireplace, DVD player, books
Peaceful Water Front Cabin on Winery Grounds
9.8 out of 10, Exceptional, (23)
"The property is easy to access and the house is filled with natural light from the huge windows. It’s a wonderful getaway if you want to unplug and enjoy a cozy few days of quiet. We found a waterfront Mexican restaurant nearby and walked to the winery next door. It’s very clean and the host is very responsive if you have any questions. Loved drinking coffee on the deck while enjoying the peaceful pond view. Left relaxed and refreshed!"
The price is NZ$477
per night
28 May - 29 May
Peaceful Water Front Cabin on Winery Grounds
Don't see what you're looking for?
See all available properties in Leonardtown
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.

Other types of properties in Leonardtown you may be interested in

Lobby
The Inn at Leonardtown, Ascend Hotel Collection
2.5 star property
9.0 out of 10, Wonderful, (94)
"The staff was very friendly and welcoming!"
The price is NZ$237
per night
9 Jun - 10 Jun
The Inn at Leonardtown, Ascend Hotel Collection
Smart TV, fireplace
Gorgeous Sunsets & Waves Heard From Bed. Why Wait?
8.8 out of 10, Excellent, (3)
"The curb appeal and overall condition of the property is not what we expected. There was a large construction crane and debris in the yard and the landscaping was not maintained. The bed sheets were not fitting the bed and the beds were not comfortable. The back yard had new grass growing with a net on the ground which is a tripping hazard. The view and sounds of the water was great but there is a steep drop off to the water with no fence or railing. For the price paid we expected a lot more."
The price is NZ$1,014
per night
21 Jun - 22 Jun
Gorgeous Sunsets & Waves Heard From Bed. Why Wait?
On the beach
River Edge Inn
2.5 star property
8.4 out of 10, Very good, (162)
"You can’t beat the location. Steps away from the Potomac River and the little boardwalk. Parking is great. Which, in a small town, can be a bit challenging. Staff is always pleasant. Perfect getaway to relax. "
The price is NZ$186
per night
22 May - 23 May
River Edge Inn
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Leonardtown holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Leonardtown. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Leonardtown. Seeing all the best attractions is bound to make you fall in love with Leonardtown. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Leonardtown short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there holiday rentals in Leonardtown?

Yes, there are holiday rentals close to the most popular sights in Leonardtown, or you can select a more secluded option if you're looking for a relaxing stay. 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.

How many holiday rentals will I find in Leonardtown?

With 12 Expedia holiday rentals, you're guaranteed 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 New Towne Neck State Park are a couple of lovely local spots to get outside and enjoy nature. Port of Leonardtown Winery and Patuxent River Naval Air Station are a couple of places you'll find in the wider area.

What’s a holiday rental in Leonardtown like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Leonardtown. Holiday rentals provide amenities such as patios, hot tubs and fire pits so you'll feel just like you're at home. If you're concerned about a sanitised environment, a holiday rental can offer a sense of privacy away from public hotel lifts and busy front desks while still allowing you to travel. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a great choice for a family trip or a small group gathering.

Recent reviews of Leonardtown properties
Expedia verified reviews

Holiday Inn Express & Suites Lexington Park-California, an IHG Hotel

Holiday Inn Express & Suites Lexington Park-California, an IHG Hotel

5/5 Excellent
Second visit
"My sister and I both agree that our room was very clean. My sister was not pleased about the sheets being tucked in all around the bed, but she made do. My bed was comfortable but the pillows are too soft (I'm used to contour memory foam). We had room service and it was excellent. Food was good. My sister enjoyed her shower. This was our second time at this hotel and we will definitely be back."
A verified traveller stayed at Holiday Inn Express & Suites Lexington Park-California, an IHG Hotel
Posted 14 hours ago
Holiday Inn Express & Suites Lexington Park-California, an IHG Hotel