Pleasant Square Cottage Rentals

Compare Cottages, Resorts, & Rentals in Pleasant Square, Ossining, New York, USA

Neighbor's house - Welcome!
10.0 (5 Reviews)
2 Bedrooms 6 Guests
Hudson River Views Briarcliff Manor Home with Deck
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10.0 (2 Reviews)
1 Bedroom 12 Guests
NYC-Area Escape Near River, Trails and MTA!
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8.7 (3 Reviews)
5 Bedrooms 11 Guests
NEW 45 Wolden Rd Ossining NY 10562
New
1 Bedroom 2 Guests
Cozy house on the Hudson
FromUS $255 per night
9.6 (70 Reviews)
1 Bedroom 2 Guests
Windrose on Hudson
FromUS $214 per night
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7.5 (45 Reviews)
244 Bedrooms 10 Guests
Windrose On Hudson
FromUS $230 per night
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8.2 (112 Reviews)
1 Bedroom 2 Guests
Polished 1BR w/Accessible Room Features + Sauna
6.0 (1 Review)
1 Bedroom 2 Guests
Near NYC! | Stylish Guestroom
FromUS $388 per night
New
1 Bedroom 4 Guests
Hudson River Views: Briarcliff Manor Home w/Deck
9.8 (13 Reviews)
4 Bedrooms 12 Guests
Castle Retreat w/Pool, BBQ, Game Room & Pets OK!
9.2 (7 Reviews)
5 Bedrooms 13 Guests
Ossining Vacation Rental Near River, Trails & MTA!
8.0 (14 Reviews)
5 Bedrooms 11 Guests

About Pleasant Square Vacation Rentals

There are over 45 amazing vacation rentals available in Pleasant Square. Choose from a variety of options including villas, hotels, and other rental properties. Explore a vast selection of luxury amenities at unbeatable prices, providing you with the ideal spot for your next getaway. Life is Better at the Cottage with Vacation Cottage, where you can discover fantastic stays in Pleasant Square.

Vacation Cottage offers numerous last-minute deals on villas, hotels, and rentals, both near you and across the globe. Whether you need accommodations for a group or event, such as a hotel or vacation rental (including cabins and private luxury villas), let us assist you. With Vacation Cottage in Pleasant Square, you can easily compare options from multiple suppliers with just a click to find the perfect price point, amenities, and style of stay for you. Whether you're seeking group discounts, private pools, hot tubs, pet-friendly options, or spacious master suite bedrooms with open-air showers, you can find it all with Vacation Cottage vacation rentals, resorts, and Airbnb-style properties in Pleasant Square. The average size of places to stay near Pleasant Square is approximately 749.93 ft², with prices averaging US $629 per night.

Vacation Cottage helps you discover the perfect holiday rental to create lasting travel memories in Pleasant Square. Prices listed often feature discounts compared to rack rates. Simply search for your destination and secure your ideal place to stay today.

Frequently Asked Questions About Pleasant Square?

What are the top cottages, summer homes, and lake houses in Pleasant Square?

How many rentals, hotels, or resorts are available in Pleasant Square?

Vacation Cottage consistently updates its selection, offering a blend of new options alongside well-established accommodations in prime locations. Currently, there are over 45 properties listed by Vacation Cottage in the Pleasant Square area for the year 2026, with this number increasing daily. By aggregating listings from various websites and travel providers, Vacation Cottage ensures a diverse array of choices for the best luxury stays in Pleasant Square.

Nearby Neighborhood (3)

NeighborhoodProperty Count
Northeast Yonkers Rental Cottages and Private Getaways in White Plains, New York 153
North Stamford Rental Cottages and Private Getaways in White Plains, New York 243
Highlands Rental Cottages and Private Getaways in White Plains, New York 167