Vacation rentals in Kent County, MD

45 available vacation rental offers

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Best vacation rentals and Airbnb offers in Kent County, MD

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

3 Mi to Washington College! Updated Home w/ Patio

Cottage, Kent County

3 Mi to Washington College! Updated Home w/ Patio is a cottage in Kent County, 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 Kent County, 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 $1,421.

From$135/night
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Eastern Shore Get Away - Kent County, MD

Eastern Shore Get Away

Apartment, Kent County

Eastern Shore Get Away is a apartment in Kent County, 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 Kent County, 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 - Kent County, MD

3 Mi to Washington College! Updated Home w/ Patio

Holiday Home, Kent County

3 Mi to Washington College! Updated Home w/ Patio is a holiday home in Kent County, 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 Kent County, 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 $1,212.

From$173/night
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Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4! - Kent County, MD

Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

Apartment, Kent County

Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4! is a apartment in Kent County, with parking, kitchen access, and room for a group. This stay gives travelers a…

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About Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4! is a apartment in Kent County, with parking, 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 wifi, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,220.

From$174/night
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Vacation rentals with a pool in Kent County, MD

Add a pool to the search when you want an easy place to cool off between outings.

A Waterfront Retreat with pier and pool. Spacious 4 bedrooms near Chestertown. - Kent County, MD

A Waterfront Retreat with pier and pool. Spacious 4 bedrooms near Chestertown.

Holiday Home, Kent County

A Waterfront Retreat with pier and pool. Spacious 4 bedrooms near Chestertown. is a holiday home in Kent County, with pool access, easy beach access, and kitchen access. This stay gives…

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About A Waterfront Retreat with pier and pool. Spacious 4 bedrooms near Chestertown.

A Waterfront Retreat with pier and pool. Spacious 4 bedrooms near Chestertown. is a holiday home in Kent County, with pool access, 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, pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $8,223.

From$1,175/night
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Inn at Haven Harbour - Kent County, MD

Inn at Haven Harbour

B & B, Kent County

Inn at Haven Harbour is a b & b in Kent County, with pool access and easy beach access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Inn at Haven Harbour

Inn at Haven Harbour is a b & b in Kent County, with pool access 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 breakfast, pool, free wifi, beachfront, and beach front.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,085.

From$248/night
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Inn at Huntingfield Creek - Kent County, MD

Inn at Huntingfield Creek

B & B, Kent County

Inn at Huntingfield Creek is a b & b in Kent County, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Inn at Huntingfield Creek

Inn at Huntingfield Creek is a b & b in Kent County, with pool 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 breakfast, pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,490.

From$320/night
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Inn at Huntingfield Creek - Kent County, MD

Inn at Huntingfield Creek

B & B, Kent County

Inn at Huntingfield Creek is a b & b in Kent County, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with…

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About Inn at Huntingfield Creek

Inn at Huntingfield Creek is a b & b in Kent County, with 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, free breakfast, pool, free wifi, and for couples.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,497.

From$320/night
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Vacation rentals with parking in Kent County, MD

Find vacation rentals that make arriving by car easier.

BAYSIDE BUNGALOW - Kent County, MD

BAYSIDE BUNGALOW

Holiday Home, Kent County

BAYSIDE BUNGALOW is a holiday home in Kent County, with easy beach access and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About BAYSIDE BUNGALOW

BAYSIDE BUNGALOW is a holiday home in Kent County, with 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, parking, free parking, and ac.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,628.

From$233/night
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Serene Waterfront Cottage with dock and gorgeous views. - Kent County, MD

Serene Waterfront Cottage with dock and gorgeous views.

Holiday Home, Kent County

Serene Waterfront Cottage with dock and gorgeous views. is a holiday home in Kent County, with pet-friendly space, easy beach access, and parking. This stay gives travelers a comfortable…

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About Serene Waterfront Cottage with dock and gorgeous views.

Serene Waterfront Cottage with dock and gorgeous views. is a holiday home in Kent County, 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, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,390.

From$341/night
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Riverside at Pear Tree Point--Waterfront Escape - Kent County, MD

Riverside at Pear Tree Point--Waterfront Escape

Holiday Home, Kent County

Riverside at Pear Tree Point--Waterfront Escape is a holiday home in Kent County, 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 Kent County, 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 - Kent County, MD

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

Holiday Home, Kent County

The Portside Manor - Queen Street Chestertown - Walking Distance to Downtown is a holiday home in Kent County, 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 Kent County, 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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Pet-friendly vacation rentals in Kent County, MD

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

Beautiful Retreat Located in Rock Hall - walk to everything! - Kent County, MD

Beautiful Retreat Located in Rock Hall - walk to everything!

Holiday Home, Kent County

Beautiful Retreat Located in Rock Hall - walk to everything! is a holiday home in Kent County, with parking, kitchen access, and a quieter setting. This stay gives travelers a comfortable…

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About Beautiful Retreat Located in Rock Hall - walk to everything!

Beautiful Retreat Located in Rock Hall - walk to everything! is a holiday home in Kent County, with parking, kitchen access, and a quieter setting. 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 $2,071.

From$296/night
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Walking distance to shopping, restaurants, entertainment, and the Chesapeake Bay - Kent County, MD

Walking distance to shopping, restaurants, entertainment, and the Chesapeake Bay

Holiday Home, Kent County

Walking distance to shopping, restaurants, entertainment, and the Chesapeake Bay is a holiday home in Kent County, with pet-friendly space, easy beach access, and kitchen access. This stay…

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About Walking distance to shopping, restaurants, entertainment, and the Chesapeake Bay

Walking distance to shopping, restaurants, entertainment, and the Chesapeake Bay is a holiday home in Kent County, 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,088.

From$298/night
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200 steps to the beach! - Kent County, MD

200 steps to the beach!

Holiday Home, Kent County

200 steps to the beach! is a holiday home in Kent County, with pet-friendly space, easy beach access, and parking. This stay gives travelers a comfortable base for exploring the area,…

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About 200 steps to the beach!

200 steps to the beach! is a holiday home in Kent County, 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, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,236.

From$319/night
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Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town - Kent County, MD

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

Holiday Home, Kent County

Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town is a holiday home in Kent County, 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 Kent County, 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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Vacation rentals with a kitchen in Kent County, MD

Compare stays with kitchen access for longer trips and easier meals.

Bayside Cottage steps from Rock Hall Harbor - Kent County, MD

Bayside Cottage steps from Rock Hall Harbor

Holiday Home, Kent County

Bayside Cottage steps from Rock Hall Harbor is a holiday home in Kent County, with pet-friendly space, easy beach access, and kitchen access. This stay gives travelers a comfortable base…

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About Bayside Cottage steps from Rock Hall Harbor

Bayside Cottage steps from Rock Hall Harbor is a holiday home in Kent County, 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,347.

From$335/night
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5 bedroom Historic Victorian by Chester River - Kent County, MD

5 bedroom Historic Victorian by Chester River

Holiday Home, Kent County

5 bedroom Historic Victorian by Chester River is a holiday home in Kent County, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for…

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About 5 bedroom Historic Victorian by Chester River

5 bedroom Historic Victorian by Chester River is a holiday home in Kent County, with parking, 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, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,510.

From$359/night
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Newly renovated single family home with attached guest suite - Kent County, MD

Newly renovated single family home with attached guest suite

Holiday Home, Kent County

Newly renovated single family home with attached guest suite is a holiday home in Kent County, with kitchen access and room for a group. This stay gives travelers a comfortable base for…

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About Newly renovated single family home with attached guest suite

Newly renovated single family home with attached guest suite is a holiday home in Kent County, with 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, kitchen, with kitchen, and kids friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,675.

From$382/night
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Harbor View Haven | Waterfront w/ Hot Tub + Dock! - Kent County, MD

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

Holiday Home, Kent County

Harbor View Haven · Waterfront w/ Hot Tub + Dock! is a holiday home in Kent County, 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 Kent County, 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 $3,353.

From$479/night
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Family-friendly vacation rentals in Kent County, MD

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

Peaceful getaway convenient to local amenities including beach, boating & food - Kent County, MD

Peaceful getaway convenient to local amenities including beach, boating & food

Cottage, Kent County

Peaceful getaway convenient to local amenities including beach, boating & food is a cottage in Kent County, with easy beach access, parking, and kitchen access. This stay gives travelers a…

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About Peaceful getaway convenient to local amenities including beach, boating & food

Peaceful getaway convenient to local amenities including beach, boating & food is a cottage in Kent County, 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, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,615.

From$231/night
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River Cottage, Chestertown - Kent County, MD

River Cottage, Chestertown

Holiday Home, Kent County

River Cottage, Chestertown is a holiday home in Kent County, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings,…

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About River Cottage, Chestertown

River Cottage, Chestertown is a holiday home in Kent County, 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 $2,171.

From$310/night
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Chesapeake Bay Getaway in Rock Hall - Kent County, MD

Chesapeake Bay Getaway in Rock Hall

Holiday Home, Kent County

Chesapeake Bay Getaway in Rock Hall is a holiday home in Kent County, with easy beach access and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Chesapeake Bay Getaway in Rock Hall

Chesapeake Bay Getaway in Rock Hall is a holiday home in Kent County, 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 wifi, kitchen, with kitchen, kids friendly, and kids friendly videos or books.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,181.

From$312/night
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Cottage with Harbor and Chesapeake Bay View in Rock Hall, MD - Kent County, MD

Cottage with Harbor and Chesapeake Bay View in Rock Hall, MD

Holiday Home, Kent County

Cottage with Harbor and Chesapeake Bay View in Rock Hall, MD is a holiday home in Kent County, with pet-friendly space, pool access, and easy beach access. This stay gives travelers a…

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About Cottage with Harbor and Chesapeake Bay View in Rock Hall, MD

Cottage with Harbor and Chesapeake Bay View in Rock Hall, MD is a holiday home in Kent County, with pet-friendly space, pool access, 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 cancellation, pool, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,184.

From$312/night
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