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Places to stay in Leonardtown

Book unique places to stay, houses, and more on Airbnb

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Popular amenities for Leonardtown places to stay

Stay near Leonardtown's top sights

The Front Porch23 locals recommend
Port of Leonardtown Winery23 locals recommend
Sweetbay Restaurant & Bar15 locals recommend
The Slice House13 locals recommend
Social12 locals recommend
Olde Town Pub11 locals recommend

Other great vacation rentals in Leonardtown

Guest favorite
Home in Montross
4.93 out of 5 average rating, 200 reviews

The Glebe

LynnRating, 5 stars1 month ago
Excellent stay at RivahLife! The views were spectacular and the home was exactly as described. Easy to find with lots of stuff for the kids and adults. Looking forward to returning during the warmer months as the fishing, boating, and swimming would be more desirable. Thanks for the high chair and portable crib. Those things really help when traveling with kids.
Guest favorite
Cottage in Lottsburg
4.98 out of 5 average rating, 83 reviews

Enchanting Edge of the World Cottage

CapriceRating, 5 stars2 months ago
This is a lovely home would definitely recommend only thing that was a little bit odd was the size of the bed upstairs and it wasn’t many pots and pans but we love our stay
Superhost
Home in Montross
4.88 out of 5 average rating, 231 reviews

Lakefront/Dock, Woods, 3 Beaches, Kayaks, Hot tub

SarahRating, 5 stars1 week ago
This cabin was everything we wanted and more! It’s in the perfect location, just a short drive to so many activities but also tucked away offering privacy. The house was so cozy it put us at ease as soon as we walked in. The owner was proactive and very quick to respond, including sending a great packing and local activity list a couple days in advance of our trip which came in very handy. Activities: This rental comes with guest passes to the private Shark Tooth Beach where our kids had so much fun finding real shark and manta ray teeth in the sand! Westmorland State Park and George Washington’s Birthplace both had great hiking and beaches for the kids. We visited Garners Produce twice where the kids fed animals and pedaled toy tractor’s while we picked up farm fresh milk and eggs. We spent our afternoons kayaking on the quiet lake soaking up the sunshine. We will definitely book another vacation at this cabin. You will not be disappointed with your stay at this little gem!
Superhost
Cabin in Lusby
4.84 out of 5 average rating, 171 reviews

2-bedroom lake-house with a magnificent view

MohamedRating, 5 stars1 week ago
Beautiful house and beautiful view. Outdoor jacuzzi with the view is not to be missed! Gorgeous and clean home. The private site made it an amazing getaway from busy life. Thank you, we will be back soon!!!
Guest favorite
Home in Colonial Beach
4.94 out of 5 average rating, 68 reviews

The Heaven at Colonial Beach

MelissaRating, 5 stars2 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 favorite
Home in Cambridge
4.98 out of 5 average rating, 53 reviews

Small, peaceful getaway

LauraRating, 5 stars1 week ago
We felt so comfortable at Heather’s place. It was extremely clean and very quiet and peaceful. It was an easy space to have our two young children in. We would definitely stay here again in the future.
Superhost
Cottage in Heathsville
4.83 out of 5 average rating, 75 reviews

Riverfront Retreat with PRIVATE POOL and BEACH!!

AllyRating, 5 stars8 months ago
This was a wonderful getaway for my family and friends. We had two toddlers that loved the river beach and pool. There were plenty of toys to keep the kids and adults busy!
Guest favorite
Villa in Hague
4.98 out of 5 average rating, 50 reviews

Sea Glass Paradise

JoshuaRating, 5 stars3 weeks ago
Frank was an excellent host, and provided my friends and I a great stay in early April. Very clean, looks as advertised, and great for a private getaway.

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