
Holiday houses in Leonardtown
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Top-rated holiday rentals in Leonardtown
Guests agree: these stays are highly rated for location, cleanliness and more.
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Other great holiday rentals in Leonardtown
Guest favourite

Home in Montross
4.93 out of 5 average rating, 198 reviewsThe Glebe
MarioRating, 5 stars4 weeks ago
Such a beautiful place!! We had such a great time at the stay and for sure will book if I’m looking to be in that area again! Thank you so much for everything
Guest favourite

Home in Cambridge
5 out of 5 average rating, 34 reviewsSerene getaway with great waterfront views!
EugeniaRating, 5 stars5 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, 35 reviewsWaterfront home with three bedrooms,3 full baths
JessicaRating, 5 stars3 months ago
Dale's place was great. After Dale gave us a tour and we went grocery shopping and settled in, we felt calm and peaceful here. There were ample amenities in the home for us to make us comfortable, and we spent our time doing as little as possible - taking in the waterfront views from the deck and the hot tub. We felt sad to leave and appreciated the time to rest and rejuvenate and reflect! We would stay here again!
Guest favourite

Home in Colonial Beach
4.94 out of 5 average rating, 67 reviewsThe Heaven at Colonial Beach
MelissaRating, 5 stars1 month 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.
Guest favourite

Home in Taylors Island
4.97 out of 5 average rating, 39 reviewsA Vacation for All, Away From It All
ChristyneRating, 5 stars3 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!
Superhost

Home in Leonardtown
4.85 out of 5 average rating, 13 reviewsGarden Getaway
ErickaRating, 5 stars2 months ago
We had our two dogs with us while we stayed for over 2 weeks waiting to move into our new house. Fenced in yard was a life saver and plenty of room for us to celebrate Christmas
Guest favourite

Cottage in Leonardtown
4.92 out of 5 average rating, 139 reviewsBreton Breeze
ChristofRating, 5 stars3 months ago
Just like the last time, a beautiful, comfortable, spacious, and peaceful place for the two of us to stay - with fantastic sunset views over the water! Our go-to place for when we come down for a visit to Southern Maryland.
Guest favourite

Home in Scotland
5 out of 5 average rating, 28 reviewsBay Front Beach House
DanielleRating, 5 stars6 months ago
Our family's stay at Dana's Bayfront Beach house was absolutely lovely. The house was spacious and looked exactly like the photos with breathtaking views from every room. We loved sitting on the deck and watching the sunrise over the bay in the mornings and the moon rising over a sky full of stars at night. We also enjoyed watching the wildlife. There were Osprey, Jellyfish, crabs, herons and gulls that we could watch from the pier. The kitchen was large and well appointed with pots and pans, dishes and cutlery and we particularly loved the Ninja toaster oven and Keurig coffee maker. We found the beds comfortable and appreciated the AC and ceiling fans which kept us cool even during a very warm and humid week! Thanks Dana! We hope to come back again soon!
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