Vacation rentals in Ossining, NY

Best vacation rentals and Airbnb offers in Ossining, NY

Cozy Cottage Get Away

Cottage, Ossining

Cozy Cottage Get Away is a cottage in Ossining, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending…

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About Cozy Cottage Get Away

Cozy Cottage Get Away is a cottage in Ossining, 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 $762.

From$109/night

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🤣🏡 \"Welcome to our basement suite, where humor and professionalism coexist!

Holiday Home, Ossining

🤣🏡 \"Welcome to our basement suite, where humor and professionalism coexist! is a holiday home in Ossining, with parking. This stay gives travelers a comfortable base for exploring the…

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About 🤣🏡 \"Welcome to our basement suite, where humor and professionalism coexist!

🤣🏡 \"Welcome to our basement suite, where humor and professionalism coexist! is a holiday home in Ossining, 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 wifi, gym, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $923.

From$132/night

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2 Mi to The Marketplace: Spring Valley Apartment

Apartment, Ossining

2 Mi to The Marketplace: Spring Valley Apartment is a apartment in Ossining, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About 2 Mi to The Marketplace: Spring Valley Apartment

2 Mi to The Marketplace: Spring Valley Apartment is a apartment in Ossining, 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 $1,576.

From$138/night

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2 Mi to The Marketplace: Spring Valley Apartment

Apartment, Ossining

2 Mi to The Marketplace: Spring Valley Apartment is a apartment in Ossining, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About 2 Mi to The Marketplace: Spring Valley Apartment

2 Mi to The Marketplace: Spring Valley Apartment is a apartment in Ossining, 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 $1,269.

From$181/night

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Vacation rentals with a pool in Ossining, NY

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

Global Luxury Suites Downtown White Plains

Apartment, Ossining

Global Luxury Suites Downtown White Plains is a apartment in Ossining, with pool access and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Global Luxury Suites Downtown White Plains

Global Luxury Suites Downtown White Plains is a apartment in Ossining, 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: pool, free wifi, parking, and onsite parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,991.

From$199/night

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Global Luxury Suites Downtown White Plains

Apartment, Ossining

Global Luxury Suites Downtown White Plains is a apartment in Ossining, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Global Luxury Suites Downtown White Plains

Global Luxury Suites Downtown White Plains is a apartment in Ossining, 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, pool, free wifi, and gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,993.

From$234/night

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Global Luxury Suites White Plains

Apartment, Ossining

Global Luxury Suites White Plains is a apartment in Ossining, with pet-friendly space, pool access, and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Global Luxury Suites White Plains

Global Luxury Suites White Plains is a apartment in Ossining, 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, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,991.

From$234/night

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Modern Studio | Upscale Amenities | Kitchen & Laundry

Apartment, Ossining

Modern Studio · Upscale Amenities · Kitchen & Laundry is a apartment in Ossining, with pet-friendly space, pool access, and kitchen access. This stay gives travelers a comfortable base for…

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About Modern Studio | Upscale Amenities | Kitchen & Laundry

Modern Studio · Upscale Amenities · Kitchen & Laundry is a apartment in Ossining, 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, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,765.

From$252/night

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Vacation rentals with parking in Ossining, NY

Find vacation rentals that make arriving by car easier.

2 Mi to NYC Train: WFH-Friendly Greenwich Apt!

Apartment, Ossining

2 Mi to NYC Train: WFH-Friendly Greenwich Apt! is a apartment in Ossining, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring…

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About 2 Mi to NYC Train: WFH-Friendly Greenwich Apt!

2 Mi to NYC Train: WFH-Friendly Greenwich Apt! is a apartment in Ossining, 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 $1,425.

From$204/night

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Garden Loft with Patios & Green Space · Westchester Retreat

Apartment, Ossining

Garden Loft with Patios & Green Space · Westchester Retreat is a apartment in Ossining, with pet-friendly space, outdoor space, and parking. This stay gives travelers a comfortable base for…

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About Garden Loft with Patios & Green Space · Westchester Retreat

Garden Loft with Patios & Green Space · Westchester Retreat is a apartment in Ossining, with pet-friendly space, outdoor 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: pet friendly, pets friendly, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,456.

From$208/night

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Palisade Suite -Cozy 1-bdr Dobbs Ferry-30 min from NYC- AC & Hudson River views

Apartment, Ossining

Palisade Suite -Cozy 1-bdr Dobbs Ferry-30 min from NYC- AC & Hudson River views is a apartment in Ossining, with parking. This stay gives travelers a comfortable base for exploring the…

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About Palisade Suite -Cozy 1-bdr Dobbs Ferry-30 min from NYC- AC & Hudson River views

Palisade Suite -Cozy 1-bdr Dobbs Ferry-30 min from NYC- AC & Hudson River views is a apartment in Ossining, 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, parking, free parking, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,610.

From$230/night

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Scenic & Serene: 3BR/3BA w Panoramic Hudson Views! A Birder's paradise

Holiday Home, Ossining

Scenic & Serene: 3BR/3BA w Panoramic Hudson Views! A Birder's paradise is a holiday home in Ossining, with parking, kitchen access, and room for a group. This stay gives travelers a…

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About Scenic & Serene: 3BR/3BA w Panoramic Hudson Views! A Birder's paradise

Scenic & Serene: 3BR/3BA w Panoramic Hudson Views! A Birder's paradise is a holiday home in Ossining, 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, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,753.

From$393/night

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Pet-friendly vacation rentals in Ossining, NY

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

Elegant Hideaway with Free Parking

Apartment, Ossining

Elegant Hideaway with Free Parking is a apartment in Ossining, with pet-friendly space and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Elegant Hideaway with Free Parking

Elegant Hideaway with Free Parking is a apartment in Ossining, 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: pet friendly, pets friendly, parking, free parking, and internet.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,742.

From$199/night

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Cozy 1-bedroom apartment in pleasant Nyack with AC

Apartment, Ossining

Cozy 1-bedroom apartment in pleasant Nyack with AC is a apartment in Ossining, with pet-friendly space and room for a group. This stay gives travelers a comfortable base for exploring the…

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About Cozy 1-bedroom apartment in pleasant Nyack with AC

Cozy 1-bedroom apartment in pleasant Nyack with AC is a apartment in Ossining, with pet-friendly space 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, pet friendly, pets friendly, washer, and dryer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,311.

From$330/night

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'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!

Apartment, Ossining

'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close! is a apartment in Ossining, with pet-friendly space and kitchen access. This stay gives travelers a…

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About 'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!

'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close! is a apartment in Ossining, 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 $2,679.

From$383/night

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Enjoy the best of both worlds

Condo, Ossining

Enjoy the best of both worlds is a condo in Ossining, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Enjoy the best of both worlds

Enjoy the best of both worlds is a condo in Ossining, 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 $2,961.

From$423/night

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Vacation rentals with a kitchen in Ossining, NY

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

Private entrance Apartment Ground Floor of House

Apartment, Ossining

Private entrance Apartment Ground Floor of House is a apartment in Ossining, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Private entrance Apartment Ground Floor of House

Private entrance Apartment Ground Floor of House is a apartment in Ossining, 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 $1,726.

From$247/night

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Downtown Studio BR | near MetroNorth Station

Apartment, Ossining

Downtown Studio BR · near MetroNorth Station is a apartment in Ossining, with pet-friendly space, pool access, and kitchen access. This stay gives travelers a comfortable base for exploring…

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About Downtown Studio BR | near MetroNorth Station

Downtown Studio BR · near MetroNorth Station is a apartment in Ossining, 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, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,765.

From$252/night

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Luxury Studio Apartment | Downtown White Plains | Gym + Clubroom

Apartment, Ossining

Luxury Studio Apartment · Downtown White Plains · Gym + Clubroom is a apartment in Ossining, with pet-friendly space, pool access, and kitchen access. This stay gives travelers a…

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About Luxury Studio Apartment | Downtown White Plains | Gym + Clubroom

Luxury Studio Apartment · Downtown White Plains · Gym + Clubroom is a apartment in Ossining, 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, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,765.

From$252/night

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White Plains Studio BR | Gym + Pool | 24hr Doorman

Apartment, Ossining

White Plains Studio BR · Gym + Pool · 24hr Doorman is a apartment in Ossining, with pet-friendly space, pool access, and kitchen access. This stay gives travelers a comfortable base for…

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About White Plains Studio BR | Gym + Pool | 24hr Doorman

White Plains Studio BR · Gym + Pool · 24hr Doorman is a apartment in Ossining, 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, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,765.

From$252/night

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Family-friendly vacation rentals in Ossining, NY

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

Family Friendly Three Bedroom Apartment outside of NYC

Apartment, Ossining

Family Friendly Three Bedroom Apartment outside of NYC is a apartment in Ossining, with pet-friendly space, kitchen access, and room for a group. This stay gives travelers a comfortable…

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About Family Friendly Three Bedroom Apartment outside of NYC

Family Friendly Three Bedroom Apartment outside of NYC is a apartment in Ossining, with pet-friendly space, 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, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,789.

From$256/night

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White Plains 1 BR | Children's Playroom | Downtown

Apartment, Ossining

White Plains 1 BR · Children's Playroom · Downtown is a apartment in Ossining, with pet-friendly space, pool access, and kitchen access. This stay gives travelers a comfortable base for…

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About White Plains 1 BR | Children's Playroom | Downtown

White Plains 1 BR · Children's Playroom · Downtown is a apartment in Ossining, 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, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,837.

From$262/night

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Family Friendly 2BR | Full Kitchen | Downtown White Plains

Apartment, Ossining

Family Friendly 2BR · Full Kitchen · Downtown White Plains is a apartment in Ossining, with pet-friendly space, pool access, and kitchen access. This stay gives travelers a comfortable base…

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About Family Friendly 2BR | Full Kitchen | Downtown White Plains

Family Friendly 2BR · Full Kitchen · Downtown White Plains is a apartment in Ossining, 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, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,506.

From$358/night

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Newly Renovated Cozy 2 Bedroom Apartment with 3 min walk to Main Street

Apartment, Ossining

Newly Renovated Cozy 2 Bedroom Apartment with 3 min walk to Main Street is a apartment in Ossining, with kitchen access and room for a group. This stay gives travelers a comfortable base…

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About Newly Renovated Cozy 2 Bedroom Apartment with 3 min walk to Main Street

Newly Renovated Cozy 2 Bedroom Apartment with 3 min walk to Main Street is a apartment in Ossining, 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, kitchen, with kitchen, kids friendly, and kids friendly videos or books.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,375.

From$482/night

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