Vacation rentals in Pawling, NY

Best Vacation rentals and Airbnb offers in Pawling, NY

Charming 1-bedroom apartment in Carmel with WiFi, AC

Apartment, Pawling

Charming 1-bedroom apartment in Carmel with WiFi, AC is a apartment in Pawling, with pool access, parking, and room for a group. This stay gives travelers a comfortable base for exploring…

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About Charming 1-bedroom apartment in Carmel with WiFi, AC

Charming 1-bedroom apartment in Carmel with WiFi, AC is a apartment in Pawling, with pool access, parking, 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: pool, parking, free parking, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,189.

From$128/night

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Serene 2-bedroom spacious apartment

Apartment, Pawling

Serene 2-bedroom spacious apartment is a apartment in Pawling, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Serene 2-bedroom spacious apartment

Serene 2-bedroom spacious apartment is a apartment in Pawling, with pool 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, pool, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,527.

From$166/night

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The Cottage by the Lake: Hudson Valley Indulgence/1 hr. from NYC/welcome pets!.

Guest House, Pawling

The Cottage by the Lake: Hudson Valley Indulgence/1 hr. from NYC/welcome pets!. is a guest house in Pawling, with pet-friendly space, pool access, and kitchen access. This stay gives…

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About The Cottage by the Lake: Hudson Valley Indulgence/1 hr. from NYC/welcome pets!.

The Cottage by the Lake: Hudson Valley Indulgence/1 hr. from NYC/welcome pets!. is a guest house in Pawling, with pet-friendly space, 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 cancellation, pool, kitchen, with kitchen, and gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,693.

From$185/night

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Trailside Base w/ Gazebo & Kayaks

Apartment, Pawling

Trailside Base w/ Gazebo & Kayaks is a apartment in Pawling, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings,…

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About Trailside Base w/ Gazebo & Kayaks

Trailside Base w/ Gazebo & Kayaks is a apartment in Pawling, 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 $1,848.

From$207/night

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Best Pawling, NY vacation rentals with parking

Find vacation rentals that make arriving by car easier.

Welcome to Hat City Danbury | A Suburban Retreat Close to It All

Apartment, Pawling

Welcome to Hat City Danbury · A Suburban Retreat Close to It All is a apartment in Pawling, with parking, kitchen access, and a quieter setting. This stay gives travelers a comfortable base…

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About Welcome to Hat City Danbury | A Suburban Retreat Close to It All

Welcome to Hat City Danbury · A Suburban Retreat Close to It All is a apartment in Pawling, 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, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,808.

From$188/night

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Beautiful mountaintop getaway for peace and quiet

Holiday Home, Pawling

Beautiful mountaintop getaway for peace and quiet is a holiday home in Pawling, with parking, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for…

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About Beautiful mountaintop getaway for peace and quiet

Beautiful mountaintop getaway for peace and quiet is a holiday home in Pawling, 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 wifi, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,683.

From$285/night

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Modern NY Home w/ Views By Hudson Valley Hiking!

Holiday Home, Pawling

Modern NY Home w/ Views By Hudson Valley Hiking! is a holiday home in Pawling, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings,…

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About Modern NY Home w/ Views By Hudson Valley Hiking!

Modern NY Home w/ Views By Hudson Valley Hiking! is a holiday home in Pawling, 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 heating.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,553.

From$388/night

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Beautiful Lake View House Overlooking Peaceful Whaley Lake

Holiday Home, Pawling

Beautiful Lake View House Overlooking Peaceful Whaley Lake is a holiday home in Pawling, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Beautiful Lake View House Overlooking Peaceful Whaley Lake

Beautiful Lake View House Overlooking Peaceful Whaley Lake is a holiday home in Pawling, 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, gym, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $5,035.

From$518/night

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Best Pet-Friendly Vacation Rentals in Pawling, NY

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

Fire Pit + On-Site Pond: Hudson Valley Home!

Holiday Home, Pawling

Fire Pit + On-Site Pond: Hudson Valley Home! is a holiday home in Pawling, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring…

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About Fire Pit + On-Site Pond: Hudson Valley Home!

Fire Pit + On-Site Pond: Hudson Valley Home! is a holiday home in Pawling, with pet-friendly 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, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,914.

From$274/night

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Fire Pit + On-Site Pond: Hudson Valley Home!

Holiday Home, Pawling

Fire Pit + On-Site Pond: Hudson Valley Home! is a holiday home in Pawling, with pet-friendly space and parking. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Fire Pit + On-Site Pond: Hudson Valley Home!

Fire Pit + On-Site Pond: Hudson Valley Home! is a holiday home in Pawling, 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,750.

From$295/night

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Candlewood Lake Retreat Extended Stay

Holiday Home, Pawling

Candlewood Lake Retreat Extended Stay is a holiday home in Pawling, with pet-friendly space, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for…

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About Candlewood Lake Retreat Extended Stay

Candlewood Lake Retreat Extended Stay is a holiday home in Pawling, with pet-friendly space, 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, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $4,601.

From$399/night

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YOIN: Whispers of Tranquility, a Zen Retreat

Holiday Home, Pawling

YOIN: Whispers of Tranquility, a Zen Retreat is a holiday home in Pawling, with pet-friendly space and a quieter setting. This stay gives travelers a comfortable base for exploring the…

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About YOIN: Whispers of Tranquility, a Zen Retreat

YOIN: Whispers of Tranquility, a Zen Retreat is a holiday home in Pawling, with pet-friendly space 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, pet friendly, pets friendly, gym, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $4,073.

From$427/night

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Best Pawling, NY vacation rentals with a kitchen

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

Modern NY Home w/ Views By Hudson Valley Hiking!

Holiday Home, Pawling

Modern NY Home w/ Views By Hudson Valley Hiking! is a holiday home in Pawling, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Modern NY Home w/ Views By Hudson Valley Hiking!

Modern NY Home w/ Views By Hudson Valley Hiking! is a holiday home in Pawling, with 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 gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,500.

From$360/night

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Incredible spacious family friendly getaway

Holiday Home, Pawling

Incredible spacious family friendly getaway is a holiday home in Pawling, with kitchen access and room for a group. This stay gives travelers a comfortable base for exploring the area,…

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About Incredible spacious family friendly getaway

Incredible spacious family friendly getaway is a holiday home in Pawling, 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, hot tub, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $4,257.

From$433/night

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Waterfront Lake Retreat Dock, Screened Porch, Fully Renovated Designer Interior

Holiday Home, Pawling

Waterfront Lake Retreat Dock, Screened Porch, Fully Renovated Designer Interior is a holiday home in Pawling, with easy beach access, parking, and kitchen access. This stay gives travelers…

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About Waterfront Lake Retreat Dock, Screened Porch, Fully Renovated Designer Interior

Waterfront Lake Retreat Dock, Screened Porch, Fully Renovated Designer Interior is a holiday home in Pawling, 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 $4,316.

From$460/night

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Beautiful lake view home on Whaley Lake in Holmes, NY.

Holiday Home, Pawling

Beautiful lake view home on Whaley Lake in Holmes, NY. is a holiday home in Pawling, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Beautiful lake view home on Whaley Lake in Holmes, NY.

Beautiful lake view home on Whaley Lake in Holmes, NY. is a holiday home in Pawling, with 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, washer, and dryer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $5,080.

From$530/night

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Our Favorite Family-Friendly Vacation Rentals in Pawling, NY

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

Fabulous 2-bedroom Creekside cottage on the historic Collins Estate.

Cottage, Pawling

Fabulous 2-bedroom Creekside cottage on the historic Collins Estate. is a cottage in Pawling, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable…

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About Fabulous 2-bedroom Creekside cottage on the historic Collins Estate.

Fabulous 2-bedroom Creekside cottage on the historic Collins Estate. is a cottage in Pawling, 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 $2,455.

From$257/night

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Fire Pit + On-site Pond: Hudson Valley Home!

Cottage, Pawling

Fire Pit + On-site Pond: Hudson Valley Home! is a cottage in Pawling, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Fire Pit + On-site Pond: Hudson Valley Home!

Fire Pit + On-site Pond: Hudson Valley Home! is a cottage in Pawling, 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,852.

From$334/night

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Litchfield Hills 3BR New Milford Retreat with Ravine Views & Covered Porch

Cottage, Pawling

Litchfield Hills 3BR New Milford Retreat with Ravine Views & Covered Porch is a cottage in Pawling, with pet-friendly space, parking, and kitchen access. This stay gives travelers a…

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About Litchfield Hills 3BR New Milford Retreat with Ravine Views & Covered Porch

Litchfield Hills 3BR New Milford Retreat with Ravine Views & Covered Porch is a cottage in Pawling, with pet-friendly 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, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,776.

From$425/night

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Modern NY Home w/ Views By Hudson Valley Hiking!

Cottage, Pawling

Modern NY Home w/ Views By Hudson Valley Hiking! is a cottage in Pawling, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

Read more

About Modern NY Home w/ Views By Hudson Valley Hiking!

Modern NY Home w/ Views By Hudson Valley Hiking! is a cottage in Pawling, 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 $3,690.

From$431/night

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