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.
Superhost
Home in Montross
4.88 out of 5 average rating, 230 reviews

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

JulieRating, 5 stars3 weeks ago
Our children (ages 15-24) loved this place! They spent hours on the lake paddle boarding and kayaking and the hot tub was perfect after a chilly morning on the water. We even found some shark teeth at Shark Tooth Beach! The home was clean and sweet and had lots of treasures from many adventures in the woods and at the beach. ❤️
Superhost
Cabin in Lusby
4.84 out of 5 average rating, 170 reviews

2-bedroom lake-house with a magnificent view

EfrainRating, 5 stars2 weeks ago
Totally amazing. The house has all the supplies you could need in your trip. Absolutely stunning views and lots of activities to do. The beach is extremely close which is something very convenient. We had a delightful visit.
Guest favorite
Home in Colonial Beach
4.94 out of 5 average rating, 67 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
Cottage in North Beach
4.98 out of 5 average rating, 146 reviews

Bell Estates-Brand New Bay View, Beautiful Cottage

TomRating, 5 stars1 week ago
My family-5 of us- spent a week at Daniel’s home in North Beach, MD in late March 2025. The home was well appointed and beautiful, close to town and less than a hour from Wash. DC. Daniel was easy to work with and quick to respond with answers to any question we had. Not being from the area it was great to have access to the informative binder he had listing restaurants and sights worth seeing. Daniel’s home was everything we had hoped it would be.
Guest favorite
Home in Cambridge
4.98 out of 5 average rating, 49 reviews

Small, peaceful getaway

IsaiahRating, 5 stars1 month ago
Loved staying here. The back yard is beautiful with a fire pit that is closed off and private. The livng room is super cozy and the tub in the bathroom is phenomenal! Also Heather had a helpful guide to getting to know the area and the kitchen fully stocked if interested in cooking a home cooked meal. Would definitely come back!
Superhost
Cottage in Heathsville
4.83 out of 5 average rating, 75 reviews

Riverfront Retreat with PRIVATE POOL and BEACH!!

AllyRating, 5 stars7 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 stars5 days 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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