Photo by Pla Jira

Book a Leonardtown Cottage

Start date: Check-in selected.
To Date
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In one month
In two months
In three months

Featured Cottages in Leonardtown

Our top choices for Leonardtown cottages

Waterfront Cottage in Beautiful Hoopers Island

10.0 out of 10, Exceptional, (78)
"We had a very nice stay and enjoyed the quiet environment and the amenities of the property. Lots of great area for walking. "
Waterfront Cottage in Beautiful Hoopers Island

A Hideaway in Hays Beach: Chesapeake Bay, 5G WiFi, 60 Second Walk to Beach

10.0 out of 10, Exceptional, (120)
"We are not strangers to the area, my wife having grown up in the area, but each time we stay on the Chesapeake we feel at home. The Hideaway is so nice that you don't want to go back your actual home! It is furnished as if it is a year-round residence, no cheap or mismatched furniture and appliances. We enjoy cooking and the kitchen is has everything you need and it works. The yard and amenities are top notch. If you enjoy bird watching, sit in the back yard and take in the bird activity...
A Hideaway in Hays Beach: Chesapeake Bay, 5G WiFi, 60 Second Walk to Beach

Relax & Renew in a WATERFRONT Cottage , private pier, kayaks, fishing, wineries.

10.0 out of 10, Exceptional, (59)
"We had a great stay. Amazing view and location! "
Relax & Renew in a WATERFRONT Cottage , private pier, kayaks, fishing, wineries.

Beachfront Hideaway - Pet Friendly, Hot Tub, EV

9.6 out of 10, Exceptional, (10)
"This was a great place for a December get-away. The location was lovely, and well stocked, with a full kitchen for those who like to cook, herbs, spices, condiments, cleaning supplies, fluffy bathrobes, q-tips, laundry detergent, etc. We needed to communicate wtih the owners a few times, and they were a pleasure to talk to. We decided to spend a little more on our get-away, and it was totally worth it. "
Beachfront Hideaway - Pet Friendly, Hot Tub, EV

Cozy Cottage with access to and partially obstructed views of the bay.

9.2 out of 10, Wonderful, (28)
"Property was cozy and clean. Owners left lights on for us knowing we had a late arrival. Would definitely stay again. "
Cozy Cottage with access to and partially obstructed views of the bay.

Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing

9.8 out of 10, Exceptional, (147)
"We enjoyed our stay at the waterfront cottage with yoga on the dock in the morning, afternoon kayaking and dinner at Captain Billy’s Seafood restaurant. Down time spent reading and nature watching made the for the perfect weekend."
Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing

Blue Heron Cottage is cozy & convenient. Renovated March 2023!

10.0 out of 10, Exceptional, (52)
"As advertised, had a great time!"
Blue Heron Cottage is cozy & convenient. Renovated March 2023!

Cozy Virginia Potomac Riverfront Cottage

9.6 out of 10, Exceptional, (43)
"The place is a little outdated but very charming...the only reason I say outdated is because we could not use the shower in the main bathroom, there was no water pressure, just a dribble. Other than that, I would stay there again."
Cozy Virginia Potomac Riverfront Cottage

Renovated, Waterfront, Large Private Deep Water Dock, Cowboy Pool, Fire Pit

10.0 out of 10, Exceptional, (51)
"Just what we needed for an extended weekend getaway with family. The view of the water was do nice. House was very clean on arrival "
Renovated, Waterfront, Large Private Deep Water Dock, Cowboy Pool, Fire Pit

Sunnyside Up - Small Dog Friendly Waterfront Cottage

10.0 out of 10, Exceptional, (21)
"It was very important to have a fenced yard for our little dog she is really part of our family enjoyed the use of the pier for veiwing the Potomac and a little light fishing the cottage was very clean and comfortable if we can we would like to return sometime "
Sunnyside Up - Small Dog Friendly Waterfront Cottage

Piney Point, private , Beach Front Cottage

10.0 out of 10, Exceptional, (91)
"Wonderful hosts, beautiful property! Already planning next years visit! "
Piney Point, private , Beach Front Cottage

Block to Beach! Fossil Hunting, Hot Tub, Coffee Bar, Screened Deck, 1hr to DC

10.0 out of 10, Exceptional, (18)
"The house was very nice and had great amenities supplied by the owners. "
Block to Beach! Fossil Hunting, Hot Tub, Coffee Bar, Screened Deck, 1hr to DC

Private Beach Front Getaway at The Sunshine Beach Cottage.

9.8 out of 10, Exceptional, (76)
"We had a lovely stay at the Sunshine Beach Cottage - it was just as we expected and easy to check in and out. We look forward to the next time we can stay! "
Private Beach Front Getaway at The Sunshine Beach Cottage.

Privacy and space with world class views

9.8 out of 10, Exceptional, (87)
"We absolutely loved our stay! What a beautiful home and property. We definitely want to come back. Enjoyed relaxing, kayaking, and Shark Tooth Island. "
Privacy and space with world class views

Waterfront Island Cottage with Loft and Private Pier

2.0 star property
10.0 out of 10, Exceptional, (1)
"This property was everything we hoped for and more. Impeccably clean, beautifully maintained, and the view was just breathtaking — even better than the photos. The host was incredibly responsive and helpful, which made our stay even more seamless and enjoyable. Every detail was perfect, and we loved every minute. We’ll definitely be back and highly recommend this gem!! Thanks, Allen. "
Waterfront Island Cottage with Loft and Private Pier

Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.

9.6 out of 10, Exceptional, (5)
"The owner was very nice "
The price is NZ$502
includes taxes & fees
30 Sept - 1 Oct
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.

2 Bedroom Cozy Beach Cottage with Water Access

9.6 out of 10, Exceptional, (19)
"Cottage was neat and tidy, close to decent eats, close to the beach, and was a lovely getaway."
2 Bedroom Cozy Beach Cottage with Water Access

Pet Friendly Delightful Waterfront Cottage on Hoopers Island, MD.

10.0 out of 10, Exceptional, (49)
"The house was exactly how the pictures showed !Cute and cozy ,and clean ! Im a country girl and felt at home sitting on the porch,enjoying the breeze. The sound of the ocean was a bonus!! Quiet and peaceful. I enjoyed the beautiful sunrises and morning walk on the dock. Overall i enjoyed my stay appreciate the hospitality of the host and would booked again !! "
Pet Friendly Delightful Waterfront Cottage on Hoopers Island, MD.

Soul Oasis - home on the Chesapeake Bay

9.8 out of 10, Exceptional, (33)
"Lovely house with tons of character. Clean and comfortable. A few steps from water. "
The price is NZ$528
includes taxes & fees
21 Sept - 22 Sept
Soul Oasis - home on the Chesapeake Bay

𝑩𝑨𝒀 𝑺𝑰𝑫𝑬 𝑹𝑬𝑻𝑹𝑬𝑨𝑻 𝐇𝐀𝐘𝐒 𝐁𝐄𝐀𝐂𝐇 step of your porch into the sand 𝐂𝐇𝐄𝐒𝐀𝐏𝐄𝐀𝐊𝐄 𝐁𝐀𝐘

10.0 out of 10, Exceptional, (123)
"Host is awesome, available to answer questions and just excited for her guests to enjoy their stay! "
𝑩𝑨𝒀 𝑺𝑰𝑫𝑬 𝑹𝑬𝑻𝑹𝑬𝑨𝑻 𝐇𝐀𝐘𝐒 𝐁𝐄𝐀𝐂𝐇 step of your porch into the sand 𝐂𝐇𝐄𝐒𝐀𝐏𝐄𝐀𝐊𝐄 𝐁𝐀𝐘
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Leonardtown Hotel Reviews

Find out more about Leonardtown

Find out more about Leonardtown

Leonardtown Cottages information

Number of reviews
1,098
Accommodation
127 Cottages
Lowest Price
NZ$502
Highest Price
NZ$528

Frequently asked questions

What is there to do in Leonardtown near my cottage?
The most useful travel accessory is a well-planned itinerary. Port of Leonardtown Winery is an excellent place to kick off your sightseeing in Leonardtown.