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Leonardtown Vacation Rentals

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Vacation Rentals in Leonardtown

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 CA $504
CA $846 total
includes taxes & fees
Jun 21 - Jun 22
Gorgeous Sunsets & Waves Heard From Bed. Why Wait?
Property grounds
Blue Heron Cottage is cozy & convenient. Renovated March 2023!
10.0 out of 10, Exceptional, (22)
"We enjoyed our stay. The cottage was perfect for our get away. It was clean and had everything we needed. The owners are very responsive to any questions."
Blue Heron Cottage is cozy & convenient. Renovated March 2023!
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 CA $149
CA $354 total
includes taxes & fees
Jun 6 - Jun 7
Peaceful Water Front Cabin on Winery Grounds
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Property grounds
Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing
9.8 out of 10, Exceptional, (107)
"The property is located in a small neighborhood right by the water. While there are houses fairly close it is quiet with beautiful views. The house is clean and has good appliances/wifi for a comfortable stay. It is a one bedroom with a big bathroom and living room. The screened in patio is good to avoid the mosquitos. One note is for those with mobility issues, the shower/bathtub has a high ledge with a thicker width to get in/out."
The price is CA $225
CA $352 total
includes taxes & fees
May 28 - May 29
Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing
Property grounds
Waterfront Cottage in Beautiful Hoopers Island
10.0 out of 10, Exceptional, (54)
"We have stayed at this property twice and love it. Very peaceful, clean, and comfortable."
Waterfront Cottage in Beautiful Hoopers Island
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
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
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)
"The house was very well maintained, beach access and views were wonderful. This location was very quiet, and if you are a nature lover this location is perfect. Many miles to walk and explore, lots of birds to watch. Very enjoyable weekend. Hope to return."
Breathtaking Views, 450 pier, kayaks, fossils, priv beach, 45 min to D.C.
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 CA $253
CA $575 total
includes taxes & fees
Jun 2 - Jun 3
Waterfront Relaxing Getaway
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 CA $178
CA $390 total
includes taxes & fees
May 27 - May 28
Soul Oasis - home on the Chesapeake Bay
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
Beach
Cozy Virginia Potomac Riverfront Cottage
9.6 out of 10, Exceptional, (23)
"We were in the area for a family wedding so spent most of our time away from the cottage. It provided a welcome morning and evening retreat, sun (or even clouds) over the water. We could have enjoyed many hours sitting in the "sun room" if we hadn't been pulled away to other activities. It was all lovely and easy. Suggest owners install a grab bar for the tub/shower. That tile step is dangerous, especially when wet."
Cozy Virginia Potomac Riverfront Cottage
Beach nearby, sun loungers, beach towels
Relax & Renew in a WATERFRONT Cottage , private pier, kayaks, fishing, wineries.
10.0 out of 10, Exceptional, (36)
"Beautiful Bay view and pier access. Super clean, comfortable and attractive cottage with TONS of activity equipment in the finished and screened in lower level. Great for kids and teens but anyone would enjoy! Pet friendly, too! Highly recommend."
Relax & Renew in a WATERFRONT Cottage , private pier, kayaks, fishing, wineries.
Property grounds
Maryland Vacation Rental w/ Private Pool & Dock
10.0 out of 10, Exceptional, (4)
"Had a great time fishing from the dock while we got out of the city for a weekend."
Maryland Vacation Rental w/ Private Pool & Dock
On the beach, sun loungers, beach towels
Private Beach Front Getaway at The Sunshine Beach Cottage.
9.8 out of 10, Exceptional, (45)
"My husband and I have been to this cottage once before. It's our secret getaway. It has everything you need plus the beach is just a few feet away. You can't find another place like this one!"
Private Beach Front Getaway at The Sunshine Beach Cottage.
Property grounds
Piney Point, private , Beach Front Cottage
10.0 out of 10, Exceptional, (73)
"Beautiful home on a beautiful piece of property on the Potomac river. The cottage was roomy enough for six adults and very comfortable. We loved the openness of the house and of course the youth of the river were incredible and very relaxing?"
Piney Point, private , Beach Front Cottage
View from property
Waterfront House with Dock, Kayaks, & Sailboat!
9.4 out of 10, Exceptional, (23)
"The house was nice and the property is spacious. Great views from the dining room table. A little steep heading down to the dock but not terrible. Very private setting, but also only 5 mins away from pretty much anything you could need. Some nice restaurants just across the bridge in Solomons Island. Would love to return in warmer weather to take advantage of the kayaks and water."
Waterfront House with Dock, Kayaks, & Sailboat!
Fridge, microwave, stovetop, coffee/tea maker
Chic Cottage w/ Private Yard: Steps to Beach!
9.8 out of 10, Exceptional, (10)
"Wonderful home, courteous home owner, excellent customer service through Evolve. The home was clean and comfortable with all of the little extras you might need when traveling or you may have forgotten. The design of the home was a great use of space and really cozy beach vibes. The porch and backyard areas were a fun surprise and my little dog did not want to leave the porch. Colonial Beach has many great restaurants and home has convenient access to beautiful river beaches and bayside...
Chic Cottage w/ Private Yard: Steps to Beach!
Smart TV, fireplace
Bay view from Calvert Cliffs, Solomons Island & State Park nearby
10.0 out of 10, Exceptional, (29)
"👍👍"
Bay view from Calvert Cliffs, Solomons Island & State Park nearby
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**
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)
"Very clean facility with a friendly staff."
The price is CA $166
CA $185 total
includes taxes & fees
Jun 9 - Jun 10
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 CA $504
CA $846 total
includes taxes & fees
Jun 21 - Jun 22
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, (164)
"pet friendly and not over priced for pet and it is on the water."
The price is CA $137
CA $156 total
includes taxes & fees
May 27 - May 28
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.

Everything you need to know about Leonardtown vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Leonardtown vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Leonardtown vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Leonardtown vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Leonardtown. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Leonardtown vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Leonardtown vacation rentals we have selected for you start as low as CA $149 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Leonardtown rentals

At Expedia, we put the best Leonardtown vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Leonardtown rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Leonardtown vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Leonardtown. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Are there vacation rentals in Leonardtown?

Yes, there are vacation rentals near the most popular local attractions in Leonardtown, or you can select a more secluded option if you want a relaxing place to 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.

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

Bay view from Calvert Cliffs, Solomons Island & State Park nearby: Located near Leonardtown, this vacation home rental is located on a lake and has a fireplace, a patio, and air-conditioning to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

How many vacation rentals will I find in Leonardtown?

With 12 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 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 larger area.

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.

Recent reviews of Leonardtown properties
Expedia verified reviews

Quality Inn Warsaw near Rappahannock River

Quality Inn Warsaw near Rappahannock River

5/5 Excellent
"Will rent again "
A verified traveller stayed at Quality Inn Warsaw near Rappahannock River
Posted 4 days ago
Quality Inn Warsaw near Rappahannock River