Pleasant Square Vacation Rentals

Compare Vacation Rentals & Rent By Owner Homes in Pleasant Square, Ossining, New York, USA

Hudson River Views: Briarcliff Manor Home w/Deck
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10.0 (2 Reviews)
4 Bedrooms 12 Guests
Neighbor's house - Welcome!
10.0 (5 Reviews)
2 Bedrooms 6 Guests
NYC-Area Escape Near River, Trails & MTA!
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8.7 (3 Reviews)
5 Bedrooms 11 Guests
Windrose on Hudson
FromR4,258 per night
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7.3 (53 Reviews)
244 Bedrooms 10 Guests
Windrose On Hudson
FromR3,101 per night
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8.4 (139 Reviews)
1 Bedroom 2 Guests
Cozy house on the Hudson
9.6 (73 Reviews)
1 Bedroom 2 Guests
Polished 1BR w/Accessible Room Features + Sauna
6.0 (1 Review)
1 Bedroom 2 Guests
Near NYC! | Stylish Guestroom
New
1 Bedroom 4 Guests
Hudson River Views: Briarcliff Manor Home w/Deck
9.8 (14 Reviews)
4 Bedrooms 12 Guests
Castle Retreat w/Pool, BBQ, Game Room & Pets OK!
9.2 (7 Reviews)
5 Bedrooms 13 Guests
NYC-Area Escape Near River, Trails & MTA!
8.2 (15 Reviews)
5 Bedrooms 11 Guests

About Pleasant Square Vacation Rentals

With more than 47 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 718.02 ft² on average, with prices averaging R10,291 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?

How many Rentbyowner vacation rentals are available in Pleasant Square?

Currently, the total number of properties listed by Rent By Owner in 2026 is over 47 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)

NeighborhoodProperty Count
North Stamford Vacation Rentals in White Plains, New York 275
Northeast Yonkers Vacation Rentals in White Plains, New York 166
Highlands Vacation Rentals in White Plains, New York 177