Photo by Pla Jira

Search Cottages in Leonardtown

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
21 Mar - 23 Mar
In two weeks
28 Mar - 30 Mar
In one month
11 Apr - 13 Apr
In two months
9 May - 11 May

Compare 106 Cottages in Leonardtown with updated reviews, rates, and availability.

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

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

9.4 out of 10, Exceptional, (18)
"My wife and I stayed two nights to visit family. Cottage was as described, very roomy and comfortable. Great location. Host was very kind. Only dislike was smell from oil heat, I've never had oil heat and not sure if that is normal."
Cozy Cottage with access to and partially obstructed views of the bay.
Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing
Property grounds

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

9.8 out of 10, Exceptional, (128)
"Great little weekend getaway very quiet and enjoyed the relaxation . Very cute and clean cottage on the water "
The price is AED 643
AED 1,110 total
includes taxes & fees
31 Mar - 1 Apr
Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing
2 Bedroom Cozy Beach Cottage with Beach Access
Fridge, microwave, oven, stovetop

2 Bedroom Cozy Beach Cottage with Beach Access

10.0 out of 10, Exceptional, (12)
"This was a great little cottage and was perfect for our stay. We wanted to be close to Valey Lee and the location was great. We will definitely consider staying again."
2 Bedroom Cozy Beach Cottage with Beach Access
Privacy and space with world class views
Property grounds

Privacy and space with world class views

9.8 out of 10, Exceptional, (80)
"House and property were great!"
Privacy and space with world class views
Hays Beach House - Hot Tub - Private Beach
Smart TV, fireplace, books

Hays Beach House - Hot Tub - Private Beach

10.0 out of 10, Exceptional, (6)
"This home sits right on the water! It is beautiful! We watched ships roll by, ducks bobbing on the water, and flocks of geese flying and landing on the water. The view from both lower and upper decks are amazing! We spent lots of time on the decks even though it was cold - we just covered ourselves with blankets. The hosts are wonderful people, always kind and patient, and gave great recommendations on shopping, sightseeing, and restaurants. They were very communicative and answered all my...
Hays Beach House - Hot Tub - Private Beach
Adorable Cottage: Fire Pit, Walk to Colonial Beach
Property grounds

Adorable Cottage: Fire Pit, Walk to Colonial Beach

10.0 out of 10, Exceptional, (7)
"Great stay, good property and great hotst"
Adorable Cottage: Fire Pit, Walk to Colonial Beach
The Hideaway in Hays Beach on Chesapeake Bay High Speed Internet 301-250-8384
Fridge, microwave, oven, stovetop

The Hideaway in Hays Beach on Chesapeake Bay High Speed Internet 301-250-8384

10.0 out of 10, Exceptional, (113)
"Not my first rental in the Scotland area and was not disappointed! Jocelyn was communicative and kind and the house was lovely, cozy and clean. The house wasn't 100% ready at check-in, but she gave us advance notice and as it happened, we were running behind anyway. The property is well equipped, steps from the beach, has a beautiful backyard for warmer months, and was a great size for two couples and an infant on a winter retreat.Our only complaints were the tap water (very smelly and not...
The Hideaway in Hays Beach on Chesapeake Bay High Speed Internet 301-250-8384
Brand New 2 Bedroom Cottage, 1 Block From Beach
Sun loungers

Brand New 2 Bedroom Cottage, 1 Block From Beach

Brand New 2 Bedroom Cottage, 1 Block From Beach
Blue Heron Cottage is cozy & convenient. Renovated March 2023!
Beach nearby

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

10.0 out of 10, Exceptional, (39)
"We enjoyed a relaxing and rejuvenating time here while we rang in the new year. The home was lovely and the community was friendly."
Blue Heron Cottage is cozy & convenient. Renovated March 2023!
Private Beach Front Getaway at The Sunshine Beach Cottage.
On the beach, sun loungers, beach towels

Private Beach Front Getaway at The Sunshine Beach Cottage.

9.8 out of 10, Exceptional, (64)
"Beautifully appointed cottage. Literally right on the water. Quiet, serene and relaxing. Loved it and will be back!"
Private Beach Front Getaway at The Sunshine Beach Cottage.
Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland
Smart TV, books

Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland

The price is AED 525
AED 1,221 total
includes taxes & fees
11 Mar - 12 Mar
Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland
Cozy Virginia Potomac Riverfront Cottage
Beach

Cozy Virginia Potomac Riverfront Cottage

9.8 out of 10, Exceptional, (34)
"This is a nice little cottage, tucked away from everything right on the river. I was looking for some peace and quiet, and that’s exactly what I got. Even though the weather wasn’t great, the sunroom still let me enjoy the views. "
Cozy Virginia Potomac Riverfront Cottage
𝑩𝑨𝒀 𝑺𝑰𝑫𝑬 𝑹𝑬𝑻𝑹𝑬𝑨𝑻 𝐇𝐀𝐘𝐒 𝐁𝐄𝐀𝐂𝐇 step of your porch into the sand 𝐂𝐇𝐄𝐒𝐀𝐏𝐄𝐀𝐊𝐄 𝐁𝐀𝐘
Property grounds

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

10.0 out of 10, Exceptional, (108)
"Perfect little getaway! Missy is wonderful to work with and the property was perfect for making memories over a holiday weekend with my family! Thanksgiving dinner, movies, games and cold plunges will be something we will always remember. Missy we would love to return!!!!"
𝑩𝑨𝒀 𝑺𝑰𝑫𝑬 𝑹𝑬𝑻𝑹𝑬𝑨𝑻 𝐇𝐀𝐘𝐒 𝐁𝐄𝐀𝐂𝐇 step of your porch into the sand 𝐂𝐇𝐄𝐒𝐀𝐏𝐄𝐀𝐊𝐄 𝐁𝐀𝐘
Scenic Sunsets star lite sky between Pax River and Wash DC. Experiences Await!
Miscellaneous

Scenic Sunsets star lite sky between Pax River and Wash DC. Experiences Await!

9.8 out of 10, Exceptional, (7)
"Great place.. quiet neighborhood.. our only regret is that the weather was to cold to enjoy it to its fullest. The sunsets are gorgeous. The host was great as well."
Scenic Sunsets star lite sky between Pax River and Wash DC. Experiences Await!
Sunnyside Up - Small Dog Friendly Waterfront Cottage
Beach/ocean view

Sunnyside Up - Small Dog Friendly Waterfront Cottage

10.0 out of 10, Exceptional, (14)
"My wife and I truly enjoyed our stay in colonial Beach! The cabin was very nicely decorated and furnished a well equipped kitchen, and we had great conversation via messaging in person with the owners of the property. We would definitely stay there again."
Sunnyside Up - Small Dog Friendly Waterfront Cottage
Block to Beach! Fossil Hunting, Hot Tub, Coffee Bar, Screened Deck, 1hr to DC
Beach nearby

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

10.0 out of 10, Exceptional, (14)
"It was very clean and not cluttered. I felt it had all the essentials, however, lacked closet space in the bed-rooms. Definitely would stay there again."
Block to Beach! Fossil Hunting, Hot Tub, Coffee Bar, Screened Deck, 1hr to DC
Beachfront Hideaway - Pet Friendly, Hot Tub, EV
Outdoor spa tub

Beachfront Hideaway - Pet Friendly, Hot Tub, EV

10.0 out of 10, Exceptional, (2)
"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
Waterfront Cottage w/ Private Beach + Deck!
TV, fireplace, books

Waterfront Cottage w/ Private Beach + Deck!

9.8 out of 10, Exceptional, (15)
"Beautiful place and very peaceful stay!"
Waterfront Cottage w/ Private Beach + Deck!
Adorable Cottage: Fire Pit, Walk to Colonial Beach
Property grounds

Adorable Cottage: Fire Pit, Walk to Colonial Beach

3.0 star property
10.0 out of 10, Exceptional, (1)
"Well appointed cottage in central location close beach and bay. Many extras not found in other rentals. Owner did a beautiful job decorating, and it was one of the cleanest rentals I've ever stayed at. "
Adorable Cottage: Fire Pit, Walk to Colonial Beach
Waterfront Island Cottage with Loft with Private Pier and Small Private Beach
Miscellaneous

Waterfront Island Cottage with Loft with Private Pier and Small Private Beach

2.0 star property
Waterfront Island Cottage with Loft with Private Pier and Small Private Beach
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.
Don't see what you're looking for?
See all available properties in Leonardtown
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Leonardtown

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

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

9.4 out of 10, Exceptional, (18)
"My wife and I stayed two nights to visit family. Cottage was as described, very roomy and comfortable. Great location. Host was very kind. Only dislike was smell from oil heat, I've never had oil heat and not sure if that is normal."
Cozy Cottage with access to and partially obstructed views of the bay.
Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing
Property grounds

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

9.8 out of 10, Exceptional, (128)
"Great little weekend getaway very quiet and enjoyed the relaxation . Very cute and clean cottage on the water "
The price is AED 643
AED 1,110 total
includes taxes & fees
31 Mar - 1 Apr
Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing
Soul Oasis - home on the Chesapeake Bay
Sun loungers, beach towels

Soul Oasis - home on the Chesapeake Bay

9.8 out of 10, Exceptional, (19)
"Beautiful place, very clean and nicely decorated. The only thing I wish was better was to have a bathroom upstairs and the stairs to be a bit easier to access, they are a bit tricky for those over 50:) nice view too!"
The price is AED 511
AED 1,094 total
includes taxes & fees
23 Mar - 24 Mar
Soul Oasis - home on the 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.

Frequently asked questions

Why book your cottage in Leonardtown with Expedia?
Expedia has some terrific cottages in Leonardtown, so get ready for a memorable vacation on nature’s doorstep. If you have a budget in mind, click on how much you want to spend and the preferred star rating of your property. Or take advantage of our filters to search for cottages with free WiFi or a pool. We’ll help you find the right place whatever your trip looks like.
How can I find cheap cottages in Leonardtown?
A good way to locate cheap cottages in Leonardtown is with Expedia’s filter tool. Tailor your search results by star rating, amenities and budget to discover awesome rates in a few clicks.