Holiday houses in Leonardtown

Find and book unique accommodation on Airbnb

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Popular amenities for Leonardtown holiday rentals

Stay near Leonardtown's top sights

The Front Porch20 locals recommend
Port of Leonardtown Winery17 locals recommend
Sweetbay Restaurant & Bar18 locals recommend
The Slice House4 locals recommend
Social17 locals recommend
Olde Town Pub18 locals recommend

Other great holiday rentals in Leonardtown

Guest favourite
Home in Montross
4.93 out of 5 average rating, 202 reviews

The Glebe

Irma VRating, 5 stars2 weeks ago
We loved the open space concept in the house. It has beautiful views and a fire pit. Beds were clean and comfortable. Very well supplied kitchen. We will come back. Thanks,
Top Guest favourite
Home in Cambridge
5 out of 5 average rating, 34 reviews

Serene getaway with great waterfront views!

EugeniaRating, 5 stars7 months ago
We recently had a wonderful stay at Travis's place, and we couldn't have felt more at home. The house is not only beautiful but also comfortable, making it the perfect retreat. It’s one of the best-stocked homes I’ve encountered on Airbnb, which made our stay even more enjoyable. Travis was a wonderful host, always responsive and ready to assist with any questions. I truly hope to return in the future. Thank you, Travis, for hosting us in your lovely home!
Superhost
Home in Lusby
4.89 out of 5 average rating, 37 reviews

Waterfront home with three bedrooms,3 full baths

JoyceRating, 5 stars3 weeks ago
Perfect weekend away! The home backed up to the Chesapeake Bay. The home was very relaxing. Would definitely stay again!
Guest favourite
Home in Colonial Beach
4.94 out of 5 average rating, 68 reviews

The Heaven at Colonial Beach

MelissaRating, 5 stars3 months ago
I’ve stayed at a lot of Airbnb’s and this was easily one of the best. Everything was exactly as described, and maybe even better than described. It had tons of amenities and a well stocked kitchen perfect for our large family. Spotless and beautiful. I highly recommend this home and would gladly stay there again.
Top Guest favourite
Home in Taylors Island
4.97 out of 5 average rating, 39 reviews

A Vacation for All, Away From It All

ChristyneRating, 5 stars5 months ago
If you are looking for a peaceful escape, you found it. Although this home can be used for large gatherings, it is also the perfect getaway for 2. My husband and I loved watching the water and the natural wildlife. DO NOT MISS THE OPPORTUNITY TO EXPERIENCE THIS HOUSE!
Guest favourite
Home in Leonardtown
4.87 out of 5 average rating, 15 reviews

Garden Getaway

LindsayRating, 5 stars2 months ago
We had the pleasure of staying here during the winter while we looked for a place to live. It was perfect! Quiet and peaceful yet super close to all restaurants and stores. We had some snowfall and the views were stunning! Once it warmed up we even got to see some wild life in the woods behind us. Lovely huge porch! Lots of space in garden escape. Can bring the entire family and more!!! Nice big driveway for easy turned around. Patrick was beyond responsive for all my questions.Whether is was just informing be as something as simple as an Internet outage in the area or we had one situation with an unsure smell. Patrick acted immediately on the problem and it was resolved within 2 hours from start to finish. Cannot recommend this place enough!
Guest favourite
Cottage in Leonardtown
4.92 out of 5 average rating, 142 reviews

Breton Breeze

ManuelRating, 5 stars3 weeks ago
We had such a wonderful stay at Breton Breeze cottage. From the moment we arrived, we felt welcomed and at ease. Jan and Tom were truly great hosts—warm, responsive, and respectful of our privacy. The cottage itself was cozy, clean, and beautifully maintained. It had everything we needed and more, making it feel like a true home away from home. What really made this place special was the peaceful setting. If you're looking to escape the hustle and bustle of the city, this is the perfect spot. Surrounded by nature, it offered us the chance to slow down, breathe, and reconnect—not just with the outdoors, but with ourselves. Even though it feels like a secluded retreat, it’s just a short drive from Leonardtown, so you’re not far from restaurants, shops, and things to do. My husband and I genuinely enjoyed every moment of our stay, and we left feeling refreshed and grateful. We would absolutely stay here again and highly recommend it to anyone looking for a quiet, restorative getaway.
Guest favourite
Home in Scotland
5 out of 5 average rating, 29 reviews

Bay Front Beach House

NicholasRating, 5 stars1 week ago
Wow what a view. Family had a wonderful stay. House is big and well equipped. Internet is strong and plenty of hot water for all. House has access to a private beach that the small grandkids enjoyed. Definitely would stay again.

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