Looking for the ideal vacation rental in Ossining? Discover an extensive gallery of private rentals offering space, comfort, and authentic local character. Owner Direct simplifies your search by matching you with verified property options.
Accommodations, Parking, Villas, Vacation homes, Spa, Cottages, Pet-friendly, Lodgings, Places to stay
Superb
2 reviews
AC, Barbecue, Crib, Dryer, Extra Bed, Fitness Equipment, Free Parking, Heater, Kitchen
Very Good
17 reviews
Apartments, Cheap, Accommodations, Parking, Pet-friendly, Lodgings, Places to stay, Family, Self-catering
Exceptional
5 reviews
AC, Free Parking, Heater, Internet, No Smoking, Spa, Tennis Court, Toys, TV
Review score
1 reviews
Apartments, Cheap, Accommodations, Parking, Lodgings, Places to stay, Family, Self-catering
Exceptional
1 reviews
AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry
Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay
AC, Free Parking, Heater, Internet, No Smoking, Spa, Tennis Court, Toys, TV
Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals
Exceptional
2 reviews
AC, Free Parking, Heater, Internet, No Smoking, Spa, Tennis Court, Toys, TV
Security/Safety, Internet, Air Conditioner, Child Friendly
Exceptional
1 reviews
AC, Internet, No Smoking
Exceptional
19 reviews
Security/Safety, Internet, Air Conditioner, Child Friendly
AC, Balcony, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry
Exceptional
13 reviews
AC, Arcade, Dryer, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking
Exceptional
5 reviews
AC, Arcade, Balcony, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater
Superb
7 reviews
Free Parking, Internet, Outdoor Space, Pool, Toys
AC, Arcade, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area
Exceptional
6 reviews
AC, Arcade, Balcony, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry
Exceptional
92 reviews
AC, Free Parking, Heater, Internet, Kitchen, Microwave, No Smoking, Toys, TV
Exceptional
2 reviews
AC, Barbecue, Dryer, Extra Bed, Fireplace, Free Parking, Heater, Hot Tub, Internet
Exceptional
4 reviews
Pro Tip:
OwnerDirectVacationRental aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Vacation Rentals in Ossining.
OwnerDirectVacationRental can help you find hotels, resorts, and rentals near many of 's top attractions, neighborhoods, and points of interest.
What makes our vacation rentals stand out?
Every vacation rentals shown on Owner Direct comes from trusted travel sources and verified hosts, so you can browse with confidence.
Compare a range of properties and find fair, transparent pricing—no hidden fees.
From oceanfront condos and coastal cottages to luxury villas and family homes, there's a rental to fit every traveler and budget.
Some of the best vacation rentals in Ossining are:
There are a lot of options in Ossining. If you plan on staying in the Ossining area, consider making a reservation for a few nights at one of these properties as these have been rated the top Vacation Rentals in Ossining
You can explore 37 verified vacation rentals in Ossining. Our listings are sourced from a range of trusted providers, giving you access to a wide selection of private homes, apartments, and unique stays—all in one place.
Vacation rental prices in Ossining vary depending on the season, property size, and location. Rates typically start from around $138 per night, with higher prices for larger homes or peak travel periods. Comparing available options can help you find a stay that matches both your budget and travel plans.
Most vacation rentals in Ossining include fully equipped kitchens, making it easy to prepare meals and enjoy a more flexible stay. This is especially useful for families, longer stays, or travelers who prefer a home-like experience.
Yes, many vacation rentals in Ossining welcome pets. Currently, 15 listings allow pets, although specific policies may vary by property. You can filter for pet-friendly options to quickly find suitable accommodations.
For popular travel periods such as holidays or peak seasons, it's recommended to book your vacation rental 60 to 90 days in advance to secure the best options. During quieter times, you may still find good availability closer to your travel dates.
Vacation rentals in Ossining often include amenities such as Fireplace/Heating, Wellness Facilities, and Internet. These features provide added comfort and convenience, making them a popular choice for travelers seeking more space and privacy.
You can use filters to narrow down your search by criteria such as number of bedrooms, guest ratings, or specific amenities like private pools or beachfront access. This makes it easier to find a property that fits your exact needs and preferences.