Vacation rentals in Kennedyville, MD

26 available vacation rental offers

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Best Vacation rentals and Airbnb offers in Kennedyville, MD

3 Mi to Washington College! Updated Home w/ Patio - Kennedyville, MD

3 Mi to Washington College! Updated Home w/ Patio

Cottage, Kennedyville

3 Mi to Washington College! Updated Home w/ Patio is a cottage in Kennedyville, with outdoor space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring…

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About 3 Mi to Washington College! Updated Home w/ Patio

3 Mi to Washington College! Updated Home w/ Patio is a cottage in Kennedyville, with outdoor space, parking, 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, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,423.

From$135/night
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WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD - Kennedyville, MD

WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD

Apartment, Kennedyville

WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD is a apartment in Kennedyville, with easy beach access and kitchen access. This stay gives travelers a…

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About WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD

WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD is a apartment in Kennedyville, with 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, kitchen, with kitchen, and beachfront.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,042.

From$149/night
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Eastern Shore Get Away - Kennedyville, MD

Eastern Shore Get Away

Apartment, Kennedyville

Eastern Shore Get Away is a apartment in Kennedyville, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Eastern Shore Get Away

Eastern Shore Get Away is a apartment in Kennedyville, with parking 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: kitchen, with kitchen, parking, free parking, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,132.

From$162/night
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3 Mi to Washington College! Updated Home w/ Patio - Kennedyville, MD

3 Mi to Washington College! Updated Home w/ Patio

Holiday Home, Kennedyville

3 Mi to Washington College! Updated Home w/ Patio is a holiday home in Kennedyville, with outdoor space, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About 3 Mi to Washington College! Updated Home w/ Patio

3 Mi to Washington College! Updated Home w/ Patio is a holiday home in Kennedyville, with outdoor space, parking, 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, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,214.

From$173/night
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Best Kennedyville, MD vacation rentals with parking

Find vacation rentals that make arriving by car easier.

Riverside at Pear Tree Point--Waterfront Escape - Kennedyville, MD

Riverside at Pear Tree Point--Waterfront Escape

Holiday Home, Kennedyville

Riverside at Pear Tree Point--Waterfront Escape is a holiday home in Kennedyville, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About Riverside at Pear Tree Point--Waterfront Escape

Riverside at Pear Tree Point--Waterfront Escape is a holiday home in Kennedyville, with easy beach access, parking, 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, hot tub, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,809.

From$401/night
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The Portside Manor - Queen Street Chestertown - Walking Distance to Downtown - Kennedyville, MD

The Portside Manor - Queen Street Chestertown - Walking Distance to Downtown

Holiday Home, Kennedyville

The Portside Manor - Queen Street Chestertown - Walking Distance to Downtown is a holiday home in Kennedyville, with parking and kitchen access. This stay gives travelers a comfortable base…

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About The Portside Manor - Queen Street Chestertown - Walking Distance to Downtown

The Portside Manor - Queen Street Chestertown - Walking Distance to Downtown is a holiday home in Kennedyville, with parking 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, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,084.

From$441/night
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Harbor View Haven | Waterfront w/ Hot Tub + Dock! - Kennedyville, MD

Harbor View Haven | Waterfront w/ Hot Tub + Dock!

Holiday Home, Kennedyville

Harbor View Haven · Waterfront w/ Hot Tub + Dock! is a holiday home in Kennedyville, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About Harbor View Haven | Waterfront w/ Hot Tub + Dock!

Harbor View Haven · Waterfront w/ Hot Tub + Dock! is a holiday home in Kennedyville, with easy beach access, parking, 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, hot tub, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,488.

From$498/night
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Brampton 1860 - Kennedyville, MD

Brampton 1860

B & B, Kennedyville

Brampton 1860 is a b & b in Kennedyville, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or…

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About Brampton 1860

Brampton 1860 is a b & b in Kennedyville, with 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 breakfast, free wifi, parking, paid parking, and fireplace.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,978.

From$383/night
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Best Pet-Friendly Vacation Rentals in Kennedyville, MD

Bring your pet along with stays that welcome four-legged travelers.

Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town - Kennedyville, MD

Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town

Holiday Home, Kennedyville

Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town is a holiday home in Kennedyville, with pet-friendly space, easy beach access, and kitchen access. This stay gives…

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About Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town

Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town is a holiday home in Kennedyville, 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 wifi, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,703.

From$529/night
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Historic Manor House on Beautiful Eastern Shore Estate - Kennedyville, MD

Historic Manor House on Beautiful Eastern Shore Estate

Holiday Home, Kennedyville

Historic Manor House on Beautiful Eastern Shore Estate is a holiday home in Kennedyville, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring…

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About Historic Manor House on Beautiful Eastern Shore Estate

Historic Manor House on Beautiful Eastern Shore Estate is a holiday home in Kennedyville, 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $9,219.

From$1,317/night
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Eagles Point Landing-Private Pool, Dock, Pickleball - Kennedyville, MD

Eagles Point Landing-Private Pool, Dock, Pickleball

Holiday Home, Kennedyville

Eagles Point Landing-Private Pool, Dock, Pickleball is a holiday home in Kennedyville, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring…

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About Eagles Point Landing-Private Pool, Dock, Pickleball

Eagles Point Landing-Private Pool, Dock, Pickleball is a holiday home in Kennedyville, 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: pool, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $10,657.

From$1,522/night
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Our Favorite Family-Friendly Vacation Rentals in Kennedyville, MD

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

Be persuaded to experience this vintage cottage by the Sassa - Kennedyville, MD

Be persuaded to experience this vintage cottage by the Sassa

Cottage, Kennedyville

Be persuaded to experience this vintage cottage by the Sassa is a cottage in Kennedyville, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Be persuaded to experience this vintage cottage by the Sassa

Be persuaded to experience this vintage cottage by the Sassa is a cottage in Kennedyville, with parking 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, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,296.

From$328/night
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Private Waterfront Cottage On Langford Creek With Hot Tub & Pier - Kennedyville, MD

Private Waterfront Cottage On Langford Creek With Hot Tub & Pier

Holiday Home, Kennedyville

Private Waterfront Cottage On Langford Creek With Hot Tub & Pier is a holiday home in Kennedyville, with easy beach access and kitchen access. This stay gives travelers a comfortable base…

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About Private Waterfront Cottage On Langford Creek With Hot Tub & Pier

Private Waterfront Cottage On Langford Creek With Hot Tub & Pier is a holiday home in Kennedyville, with 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, hot tub, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,466.

From$495/night
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Countryside Cottage in Sassafras - Kennedyville, MD

Countryside Cottage in Sassafras

Holiday Home, Kennedyville

Countryside Cottage in Sassafras is a holiday home in Kennedyville, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Countryside Cottage in Sassafras

Countryside Cottage in Sassafras is a holiday home in Kennedyville, with parking 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, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $4,064.

From$581/night
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