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Holiday Homes in Leonardtown

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Check prices for these dates

Next weekend
7 Feb - 9 Feb
In two weeks
14 Feb - 16 Feb
In one month
28 Feb - 2 Mar
In two months
28 Mar - 30 Mar

Featured Holiday Homes in Leonardtown

Screened Patio, Deck & Grill: Saint Inigoes Home!
Outdoor dining

Screened Patio, Deck & Grill: Saint Inigoes Home!

Screened Patio, Deck & Grill: Saint Inigoes Home!
Large RENOVATED 6 bedroom 5 bath private home with LOTS of space!
Fridge, microwave, oven, stovetop

Large RENOVATED 6 bedroom 5 bath private home with LOTS of space!

9.6 out of 10, Exceptional, (29)
"This was our third year celebrating our family Thanksgiving in this home. Three generations coming from three different states. Location offers an easy drive for everyone, and the home is large enough for us spread out yet gather for meals. The host listened to our comments from previous years and addressed all of our concerns. Will be returning again."
Large RENOVATED 6 bedroom 5 bath private home with LOTS of space!
Colonial Beach Cottage, 7 minutes walk to beach!
Miscellaneous

Colonial Beach Cottage, 7 minutes walk to beach!

9.6 out of 10, Exceptional, (24)
"The overall cleanliness of the cottage was a 10/10. Everything was neat and clean. Other than snow not being shoveled and the steps being slippery I have no complaints. "
Colonial Beach Cottage, 7 minutes walk to beach!
Beach Cottage With A Spectacular View ~ Your Own Private Beach ~ Includes Kayaks
On the beach

Beach Cottage With A Spectacular View ~ Your Own Private Beach ~ Includes Kayaks

10.0 out of 10, Exceptional, (69)
"Property provides relaxation and entertainment for all ages. If you can think of it, it's already there. Clean, well-kept everything in working order. Will definitely consider a longer stay in the future. Thank you for this opportunity. "
Beach Cottage With A Spectacular View ~ Your Own Private Beach ~ Includes Kayaks
Hawthorn House Remodeled 3BR Walk to Town!
Property grounds

Hawthorn House Remodeled 3BR Walk to Town!

10.0 out of 10, Exceptional, (3)
"This house has been beautifully restored and was the perfect getaway for 2 couples & 2 kids under 5. The rooms are spacious, the front porch & back deck are great outdoor spaces, and the kids loved running around the backyard and hanging in the hammocks. The linens were soft & clean & plentiful, and we had everything we needed in the kitchen & for using the grill. Also, the host was very responsive & accommodating. We literally couldn’t ask for more in a vacation rental house. Thank you for...
Hawthorn House Remodeled 3BR Walk to Town!
Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier
On the beach

Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier

10.0 out of 10, Exceptional, (112)
"Location was perfect for what we needed (quiet, on the beach, great views). Family & pup will definitely be back! We wished we could have stayed longer. Owner communication was wonderful, we never needed anything but knew we could reach out if we did. Very comfortable experience throughout. "
Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier
Inviting and Serene Home on Monroe Bay Creek
Fridge, microwave, oven, stovetop

Inviting and Serene Home on Monroe Bay Creek

10.0 out of 10, Exceptional, (63)
"This was a great stay. Very nice, comfortable, great layout, convenient location. I highly recommend. "
Inviting and Serene Home on Monroe Bay Creek
Belle of the Chesapeake Bay
Beach

Belle of the Chesapeake Bay

9.2 out of 10, Wonderful, (12)
"Our granddaughters live in the neighborhood and our youngest was having her first birthday! It was just my husband and myself, way more house than we needed but tons more comfortable than a hotel. The winter views of the Bay from the living room were awesome. I highly recommend you make a cup of coffee and watch the sunrise. A few surprises with the house itself, the most egregious for me was the fireplace pictured is not functional. The hosts have done a nice job with this house and are still...
Belle of the Chesapeake Bay
Waterfront Lusby Retreat w/ Deep-Water Dock & Slip
Beach

Waterfront Lusby Retreat w/ Deep-Water Dock & Slip

9.8 out of 10, Exceptional, (11)
"Would stay again. Steps down to the water are a challenge"
Waterfront Lusby Retreat w/ Deep-Water Dock & Slip
Sea Glass Beach House! Large sand beach, dock and hot tub! Pets welcome!
Property grounds

Sea Glass Beach House! Large sand beach, dock and hot tub! Pets welcome!

10.0 out of 10, Exceptional, (17)
"Great stay, easy check-in/check-out, highly recommend"
Sea Glass Beach House! Large sand beach, dock and hot tub! Pets welcome!
Stunning Water Front Home 90 minutes from DC with Deepwater Dock.Bring your boat
Property grounds

Stunning Water Front Home 90 minutes from DC with Deepwater Dock.Bring your boat

9.8 out of 10, Exceptional, (19)
"The house was very comfortable and well stocked! It has everything you need for a relaxing time. "
Stunning Water Front Home 90 minutes from DC with Deepwater Dock.Bring your boat
Stylish & Modern Waterfront retreat, Serene and with great views,1Hr to DC
Terrace/patio

Stylish & Modern Waterfront retreat, Serene and with great views,1Hr to DC

10.0 out of 10, Exceptional, (11)
"Great place to stay while in the area. Thank you!"
Stylish & Modern Waterfront retreat, Serene and with great views,1Hr to DC
Spectacular Waterfront Retreat with Pier
Property grounds

Spectacular Waterfront Retreat with Pier

10.0 out of 10, Exceptional, (7)
"Classic cottage, very clean and well-supplied. Comfy bed in main bedroom! Beautiful property on the river - quiet and peaceful. Lovely sitting areas both inside and out. Restorative!"
Spectacular Waterfront Retreat with Pier
18-Acre Waterfront Sanctuary: Peace & Privacy
Aerial view

18-Acre Waterfront Sanctuary: Peace & Privacy

9.6 out of 10, Exceptional, (5)
"Lots to do and very quiet."
18-Acre Waterfront Sanctuary: Peace & Privacy
Secluded River Front Cottage
Beach

Secluded River Front Cottage

9.4 out of 10, Exceptional, (3)
"The home and property are exactly as advertised. I loved being five minutes away from Point Lookout, the sunset views, and the waterfront. "
Secluded River Front Cottage
Serenity Bay-Relaxing, Spacious House-Private Pool-6 bdrms-5baths
Beach nearby

Serenity Bay-Relaxing, Spacious House-Private Pool-6 bdrms-5baths

9.0 out of 10, Wonderful, (14)
"My family enjoyed our stay over Thanksgiving. Three generations with different needs and the house accommodated us well."
Serenity Bay-Relaxing, Spacious House-Private Pool-6 bdrms-5baths
Waterfront Cottage with Pier & Boatlift on the Beautiful Potomac River
Marina

Waterfront Cottage with Pier & Boatlift on the Beautiful Potomac River

9.8 out of 10, Exceptional, (10)
"Awesome property/location/amenities/host! We enjoyed every nano-second of our stay, and that is due to the host/hostess and the property they maintain and provide in the best way possible. We couldn't have wished for a better experience and hope to visit again and again. If you are planning to visit Cobb Island, this is the property you want to be at. Every inquiry before arrival was responded to promptly, and upon arrival, we were amazed at how clean and well addressed all our needs were...
Waterfront Cottage with Pier & Boatlift on the Beautiful Potomac River
Your private beach retreat in historic St. Mary's
Outdoor spa tub

Your private beach retreat in historic St. Mary's

10.0 out of 10, Exceptional, (20)
"We had a wonderful stay at this property. The house was in mint condition and had all the amenities we needed. Enjoyed the hot tub, kayaks, the fire pit, and the dock. Great place to spend a relaxing long weekend. "
Your private beach retreat in historic St. Mary's
Beachy Maryland A-Frame: Steps to Chesapeake Bay!
Interior

Beachy Maryland A-Frame: Steps to Chesapeake Bay!

9.8 out of 10, Exceptional, (9)
"I loved this sweet A frame home! Celebrated my 48th birthday with a girls' trip and we all loved it. Enjoyed fires and Christmas movies each night. House has a lot of space and is so comfortable. Loved the views of the Bay, particularly from the sunroom and porch. Found quite a bit of sea glass on the neighborhood beach, as well as at the house beach during low tide. Owner was incredibly responsive and went above and beyond. Great place. Would highly recommend. "
Beachy Maryland A-Frame: Steps to Chesapeake Bay!
Luxury Modern Waterfront Retreat
Fridge, microwave, oven, stovetop

Luxury Modern Waterfront Retreat

9.8 out of 10, Exceptional, (10)
"Very nice inside, love all the windows"
The price is AU$747
includes taxes & fees
28 Jan - 29 Jan
Luxury Modern Waterfront Retreat
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.
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Other property types in Leonardtown

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, (126)
"Great location by the water and far enough from the hustle and bustle. Perfect size cottage for us for a relaxing new year’s celebration. "
Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing
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.

9.6 out of 10, Exceptional, (17)
"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.
Cheery, Peaceful Water Front Cabin on Winery Grounds
TV, fireplace, DVD player, books

Cheery, Peaceful Water Front Cabin on Winery Grounds

9.8 out of 10, Exceptional, (39)
"I wanted a cozy retreat from DC over the holiday, and this was perfect. The dog loved running around the lot and taking walks around the vineyard. I loved the views of the pond, the eagles, and having plenty of space for puzzles, drawing, and reading. I took a speaker for tunes. No wifi but my cell worked fine, as did my hot spot. (Both are Verizon.) The king size bed is super comfortable, and I appreciated the nicer linens.Great location — 10 minutes from groceries, 15 minutes from downtown and...
The price is AU$463
includes taxes & fees
28 Jan - 29 Jan
Cheery, Peaceful Water Front Cabin on Winery Grounds
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.