Vacation rentals in Leonardtown, MD

Best vacation rentals and Airbnb offers in Leonardtown, MD

Riverside House w/ Kayaks, Piano & Fireplace

Holiday Home, Leonardtown

Riverside House w/ Kayaks, Piano & Fireplace is a holiday home in Leonardtown, with pet-friendly space and easy beach access. This stay gives travelers a comfortable base for exploring the…

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About Riverside House w/ Kayaks, Piano & Fireplace

Riverside House w/ Kayaks, Piano & Fireplace is a holiday home in Leonardtown, with pet-friendly space and easy beach access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, pet friendly, pets friendly, beachfront, and beach front.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $3,114.

From$344/night

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Chesapeake Bay Vacation Rental w/ Boat Dock!

Holiday Home, Leonardtown

Chesapeake Bay Vacation Rental w/ Boat Dock! is a holiday home in Leonardtown, with pet-friendly space, easy beach access, and parking. This stay gives travelers a comfortable base for…

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About Chesapeake Bay Vacation Rental w/ Boat Dock!

Chesapeake Bay Vacation Rental w/ Boat Dock! is a holiday home in Leonardtown, with pet-friendly space, easy beach access, and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and parking.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $2,322.

From$242/night

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2 Mi to Lighthouse: Waterfront Home w/ Dock!

Holiday Home, Leonardtown

2 Mi to Lighthouse: Waterfront Home w/ Dock! is a holiday home in Leonardtown, with pet-friendly space, easy beach access, and parking. This stay gives travelers a comfortable base for…

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About 2 Mi to Lighthouse: Waterfront Home w/ Dock!

2 Mi to Lighthouse: Waterfront Home w/ Dock! is a holiday home in Leonardtown, with pet-friendly space, easy beach access, and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and parking.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $3,067.

From$342/night

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Swim, Fish & Explore! Family Hague Haven w/ Dock

Cottage, Leonardtown

Swim, Fish & Explore! Family Hague Haven w/ Dock is a cottage in Leonardtown, with pet-friendly space, kitchen access, and room for a group. This stay gives travelers a comfortable base for…

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About Swim, Fish & Explore! Family Hague Haven w/ Dock

Swim, Fish & Explore! Family Hague Haven w/ Dock is a cottage in Leonardtown, with pet-friendly space, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $1,489.

From$126/night

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Family-friendly vacation rentals in Leonardtown, MD

Plan a trip with stays that give families more room to spread out.

Chesapeake Bay Vacation Rental w/ Boat Dock!

Cottage, Leonardtown

Chesapeake Bay Vacation Rental w/ Boat Dock! is a cottage in Leonardtown, with pet-friendly space, easy beach access, and kitchen access. This stay gives travelers a comfortable base for…

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About Chesapeake Bay Vacation Rental w/ Boat Dock!

Chesapeake Bay Vacation Rental w/ Boat Dock! is a cottage in Leonardtown, with pet-friendly space, easy beach access, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $2,410.

From$279/night

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2 Mi to Lighthouse: Waterfront Home w/ Dock!

Cottage, Leonardtown

2 Mi to Lighthouse: Waterfront Home w/ Dock! is a cottage in Leonardtown, with pet-friendly space, easy beach access, and kitchen access. This stay gives travelers a comfortable base for…

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About 2 Mi to Lighthouse: Waterfront Home w/ Dock!

2 Mi to Lighthouse: Waterfront Home w/ Dock! is a cottage in Leonardtown, with pet-friendly space, easy beach access, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $3,185.

From$384/night

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Riverside House w/ Kayaks, Piano & Fireplace

Cottage, Leonardtown

Riverside House w/ Kayaks, Piano & Fireplace is a cottage in Leonardtown, with pet-friendly space. This stay gives travelers a comfortable base for exploring the area, relaxing between…

Read more

About Riverside House w/ Kayaks, Piano & Fireplace

Riverside House w/ Kayaks, Piano & Fireplace is a cottage in Leonardtown, with pet-friendly space. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, hot tub, free wifi, pet friendly, and pets friendly.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $3,234.

From$386/night

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Maryland Vacation Rental w/ Private Pool & Dock

Cottage, Leonardtown

Maryland Vacation Rental w/ Private Pool & Dock is a cottage in Leonardtown, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring the area,…

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About Maryland Vacation Rental w/ Private Pool & Dock

Maryland Vacation Rental w/ Private Pool & Dock is a cottage in Leonardtown, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, free wifi, pet friendly, and pets friendly.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $4,370.

From$517/night

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