Compare Vacation Rentals & Rent By Owner Homes in Pleasant Square, Ossining, New York, USA
About Pleasant Square Vacation Rentals
With more than 87 Pleasant Square vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Rent By Owner Homes (RBOs) and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at an RBO property in Pleasant Square.
Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With RentByOwner Pleasant Square, you have the flexibility of comparing different options of various deals with a single click. Looking for an RBO with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner (RBOs), and other popular Airbnb-style properties in Pleasant Square. Places to stay near Pleasant Square are 1035.28 ft² on average, with prices averaging US $535 a night.
RentByOwner makes it easy and safe to find and compare vacation rentals in Pleasant Square with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.
Frequently Asked Questions About Pleasant Square?
What are the top vacation rentals in Pleasant Square?
- River front with large decks and dock over the Hudson
- Beautiful Brand New Private Duplex Unit in Lower Hudson Valley "Stone Haven"
- Newly Renovated Cozy 2 Bedroom Apartment with 3 min walk to Main Street
- Family home in one of NY top-ranked school districts with Tennis court
- Neighbor's house - Welcome!
- The Best of Both Worlds: For nature lovers but close to New York City
- The Red Hill Retreat - Woods Water History Privacy
- Hudson River Views Briarcliff Manor Home with Deck
- 'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!
- Croton Nook - Cozy Getaway
How many Rentbyowner vacation rentals are available in Pleasant Square?
Currently, the total number of properties listed by Rent By Owner in 2025 is over 87 in the Pleasant Square area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Pleasant Square.
Nearby Neighborhood (3)
| Neighborhood | Property Count |
|---|---|
| Northeast Yonkers Vacation Rentals in White Plains, New York | 122 |
| North Stamford Vacation Rentals in White Plains, New York | 187 |
| Highlands Vacation Rentals in White Plains, New York | 109 |
