Vacation rentals in Chestertown, MD

49 available vacation rental offers

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Best Vacation rentals and Airbnb offers in Chestertown, MD

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

3 Mi to Washington College! Updated Home w/ Patio

Holiday Home, Chestertown

3 Mi to Washington College! Updated Home w/ Patio is a holiday home in Chestertown, 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 Chestertown, 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 $1,341.

From$86/night
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3 Mi to Washington College! Updated Home w/ Patio - Chestertown, MD

3 Mi to Washington College! Updated Home w/ Patio

Cottage, Chestertown

3 Mi to Washington College! Updated Home w/ Patio is a cottage in Chestertown, 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 Chestertown, 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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Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4! - Chestertown, MD

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

Apartment, Chestertown

Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4! is a apartment in Chestertown, 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 Chestertown, 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 $1,363.

From$143/night
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Eastern Shore Get Away - Chestertown, MD

Eastern Shore Get Away

Apartment, Chestertown

Eastern Shore Get Away is a apartment in Chestertown, 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 Chestertown, 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 $1,200.

From$143/night
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Browse Vacation Rentals with a Pool in Chestertown, 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. - Chestertown, MD

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

Holiday Home, Chestertown

A Waterfront Retreat with pier and pool. Spacious 4 bedrooms near Chestertown. is a holiday home in Chestertown, 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 Chestertown, 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 $9,080.

From$995/night
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Inn at Haven Harbour - Chestertown, MD

Inn at Haven Harbour

B & B, Chestertown

Inn at Haven Harbour is a b & b in Chestertown, 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 Chestertown, 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 $2,197.

From$263/night
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Inn at Huntingfield Creek - Chestertown, MD

Inn at Huntingfield Creek

B & B, Chestertown

Inn at Huntingfield Creek is a b & b in Chestertown, 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 Chestertown, 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 - Chestertown, MD

Inn at Huntingfield Creek

B & B, Chestertown

Inn at Huntingfield Creek is a b & b in Chestertown, 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 Chestertown, 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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Best Chestertown, MD vacation rentals with parking

Find vacation rentals that make arriving by car easier.

Cute waterfront apartment -- 8 min from the beach! - Chestertown, MD

Cute waterfront apartment -- 8 min from the beach!

Apartment, Chestertown

Cute waterfront apartment -- 8 min from the beach! is a apartment in Chestertown, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About Cute waterfront apartment -- 8 min from the beach!

Cute waterfront apartment -- 8 min from the beach! is a apartment in Chestertown, 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, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,695.

From$179/night
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BAYSIDE BUNGALOW - Chestertown, MD

BAYSIDE BUNGALOW

Holiday Home, Chestertown

BAYSIDE BUNGALOW is a holiday home in Chestertown, 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 Chestertown, 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 $1,726.

From$200/night
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Harbor View Haven | Waterfront w/ Hot Tub + Dock! - Chestertown, MD

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

Holiday Home, Chestertown

Harbor View Haven · Waterfront w/ Hot Tub + Dock! is a holiday home in Chestertown, 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 Chestertown, 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 $3,829.

From$396/night
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Victorian Hideaway: Beautiful Exterior, Modern interior - Chestertown, MD

Victorian Hideaway: Beautiful Exterior, Modern interior

Holiday Home, Chestertown

Victorian Hideaway: Beautiful Exterior, Modern interior is a holiday home in Chestertown, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Victorian Hideaway: Beautiful Exterior, Modern interior

Victorian Hideaway: Beautiful Exterior, Modern interior is a holiday home in Chestertown, 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, hot tub, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $5,641.

From$643/night
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Best Pet-Friendly Vacation Rentals in Chestertown, MD

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

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

Beautiful Retreat Located in Rock Hall - walk to everything!

Holiday Home, Chestertown

Beautiful Retreat Located in Rock Hall - walk to everything! is a holiday home in Chestertown, 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 Chestertown, 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 $2,284.

From$229/night
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Walking distance to shopping, restaurants, entertainment, and the Chesapeake Bay - Chestertown, MD

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

Holiday Home, Chestertown

Walking distance to shopping, restaurants, entertainment, and the Chesapeake Bay is a holiday home in Chestertown, 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 Chestertown, 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 $2,305.

From$240/night
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Cottage with Harbor and Chesapeake Bay View in Rock Hall, MD - Chestertown, MD

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

Holiday Home, Chestertown

Cottage with Harbor and Chesapeake Bay View in Rock Hall, MD is a holiday home in Chestertown, 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 Chestertown, 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 $2,410.

From$255/night
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Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town - Chestertown, MD

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

Holiday Home, Chestertown

Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town is a holiday home in Chestertown, 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 Chestertown, 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 $4,087.

From$428/night
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Best Chestertown, MD vacation rentals with a kitchen

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

200 steps to the beach! - Chestertown, MD

200 steps to the beach!

Holiday Home, Chestertown

200 steps to the beach! is a holiday home in Chestertown, 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 Chestertown, 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 $2,469.

From$261/night
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Bayside Cottage steps from Rock Hall Harbor - Chestertown, MD

Bayside Cottage steps from Rock Hall Harbor

Holiday Home, Chestertown

Bayside Cottage steps from Rock Hall Harbor is a holiday home in Chestertown, 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 Chestertown, 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 $2,462.

From$273/night
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Serene Waterfront Cottage with dock and gorgeous views. - Chestertown, MD

Serene Waterfront Cottage with dock and gorgeous views.

Holiday Home, Chestertown

Serene Waterfront Cottage with dock and gorgeous views. is a holiday home in Chestertown, 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 Chestertown, 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 $2,638.

From$280/night
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5 bedroom Historic Victorian by Chester River - Chestertown, MD

5 bedroom Historic Victorian by Chester River

Holiday Home, Chestertown

5 bedroom Historic Victorian by Chester River is a holiday home in Chestertown, 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 Chestertown, 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 $2,615.

From$313/night
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Our Favorite Family-Friendly Vacation Rentals in Chestertown, MD

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

Charming cottage with Pool Access and WiFi in lovely Rock Hall - Chestertown, MD

Charming cottage with Pool Access and WiFi in lovely Rock Hall

Cottage, Chestertown

Charming cottage with Pool Access and WiFi in lovely Rock Hall is a cottage in Chestertown, with pool access and parking. This stay gives travelers a comfortable base for exploring the…

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About Charming cottage with Pool Access and WiFi in lovely Rock Hall

Charming cottage with Pool Access and WiFi in lovely Rock Hall is a cottage in Chestertown, with pool 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, pool, free wifi, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,762.

From$189/night
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Peaceful getaway convenient to local amenities including beach, boating & food - Chestertown, MD

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

Cottage, Chestertown

Peaceful getaway convenient to local amenities including beach, boating & food is a cottage in Chestertown, 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 Chestertown, 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 $1,783.

From$191/night
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Chesapeake Bay Getaway in Rock Hall - Chestertown, MD

Chesapeake Bay Getaway in Rock Hall

Holiday Home, Chestertown

Chesapeake Bay Getaway in Rock Hall is a holiday home in Chestertown, 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 Chestertown, 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 $2,312.

From$251/night
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River Cottage, Chestertown - Chestertown, MD

River Cottage, Chestertown

Holiday Home, Chestertown

River Cottage, Chestertown is a holiday home in Chestertown, 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 Chestertown, 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 $2,279.

From$262/night
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