Vacation rentals in Chestertown, NY

Best vacation rentals and Airbnb offers in Chestertown, NY

10 ★ 3 reviews

< 1 Mi to Beach: Peaceful Brant Lake Home!

Cottage, Chestertown

< 1 Mi to Beach: Peaceful Brant Lake Home! is a cottage in Chestertown, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About < 1 Mi to Beach: Peaceful Brant Lake Home!

< 1 Mi to Beach: Peaceful Brant Lake Home! 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, free wifi, kitchen, with kitchen, and parking.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $2,426.

From$277/night

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North Creek All Season Rental

Holiday Home, Chestertown

North Creek All Season Rental is a holiday home in Chestertown, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending…

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About North Creek All Season Rental

North Creek All Season Rental is a holiday home in Chestertown, 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 cancellation, free wifi, parking, paid parking, and ac.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $1,283.

From$150/night

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Shady Acres

Holiday Home, Chestertown

Shady Acres is a holiday home in Chestertown, with pet-friendly space. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with…

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About Shady Acres

Shady Acres is a holiday home in Chestertown, 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: pet friendly, pets friendly, fireplace, outdoor fireplace, and heating.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $1,368.

From$153/night

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Rustic Adirondacks Home w/ Hot Tub & Lake Access!

Holiday Home, Chestertown

Rustic Adirondacks Home w/ Hot Tub & Lake Access! is a holiday home in Chestertown, with pet-friendly space. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Rustic Adirondacks Home w/ Hot Tub & Lake Access!

Rustic Adirondacks Home w/ Hot Tub & Lake Access! is a holiday home in Chestertown, 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: hot tub, free wifi, pet friendly, and pets friendly.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $1,724.

From$170/night

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Family-friendly vacation rentals in Chestertown, NY

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

North Creek Chalet w/ Fire Pit Near Gore Mountain!

Cottage, Chestertown

North Creek Chalet w/ Fire Pit Near Gore Mountain! is a cottage in Chestertown, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About North Creek Chalet w/ Fire Pit Near Gore Mountain!

North Creek Chalet w/ Fire Pit Near Gore Mountain! is a cottage 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, free wifi, kitchen, with kitchen, and parking.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $2,259.

From$261/night

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Adirondack Retreat w/ Heated Pool & Scenic Views!

Cottage, Chestertown

Adirondack Retreat w/ Heated Pool & Scenic Views! is a cottage in Chestertown, with pool access, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for…

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About Adirondack Retreat w/ Heated Pool & Scenic Views!

Adirondack Retreat w/ Heated Pool & Scenic Views! is a cottage in Chestertown, with pool access, 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, pool, free wifi, kitchen, and with kitchen.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $3,917.

From$456/night

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Family Oriented Cottage

Holiday Home, Chestertown

Family Oriented Cottage is a holiday home in Chestertown, with easy beach access and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Family Oriented Cottage

Family Oriented Cottage is a holiday home in Chestertown, with easy beach 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: beachfront, beach front, fireplace, outdoor fireplace, and heating.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $4,188.

From$469/night

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Private Dock & Beach! Lakefront, Fire Pit, Boats

Cottage, Chestertown

Private Dock & Beach! Lakefront, Fire Pit, Boats is a cottage in Chestertown, with pet-friendly space, easy beach access, and kitchen access. This stay gives travelers a comfortable base…

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About Private Dock & Beach! Lakefront, Fire Pit, Boats

Private Dock & Beach! Lakefront, Fire Pit, Boats is a cottage 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, Oct 3 - Sat, Oct 10 · 7 nights · total from $4,742.

From$579/night

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Pet-friendly vacation rentals in Chestertown, NY

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

Mountain Adventure Ski Chalet near Gore

Holiday Home, Chestertown

Mountain Adventure Ski Chalet near Gore is a holiday home in Chestertown, with pet-friendly space and parking. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Mountain Adventure Ski Chalet near Gore

Mountain Adventure Ski Chalet near Gore is a holiday home in Chestertown, with pet-friendly space 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 wifi, pet friendly, pets friendly, parking, and paid parking.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $2,070.

From$230/night

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The Barn on Bartman

Holiday Home, Chestertown

The Barn on Bartman is a holiday home in Chestertown, with pet-friendly space. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending…

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About The Barn on Bartman

The Barn on Bartman is a holiday home in Chestertown, 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: hot tub, pet friendly, pets friendly, fireplace, and outdoor fireplace.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $3,753.

From$420/night

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A-Frame Log Home w/ Game Room Near Lake George!

Holiday Home, Chestertown

A-Frame Log Home w/ Game Room Near Lake George! is a holiday home in Chestertown, with pet-friendly space and parking. This stay gives travelers a comfortable base for exploring the area,…

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About A-Frame Log Home w/ Game Room Near Lake George!

A-Frame Log Home w/ Game Room Near Lake George! is a holiday home in Chestertown, with pet-friendly space 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 $4,913.

From$589/night

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A-frame Log Home w/ Game Room Near Lake George!

Cottage, Chestertown

A-frame Log Home w/ Game Room Near Lake George! is a cottage in Chestertown, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About A-frame Log Home w/ Game Room Near Lake George!

A-frame Log Home w/ Game Room Near Lake George! is a cottage in Chestertown, with pet-friendly space 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 $5,448.

From$640/night

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