Hotels in Pleasant Square, NY: Compare 10+ Sites & Save

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29 Best Hotels in Pleasant Square (Starting from $120)

Windrose on Hudson
Windrose on Hudson
Hotel
Ossining, NY, USA
2.5k from Pleasant Square center

Luxury, Cheap, Accommodations, Parking, 4-star, Lodgings, Places to stay, Family, Accessible hotels

7.0

Good

3 reviews

$214
Average price / night
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Hotel Nyack, a JdV by Hyatt Hotel
Hotel Nyack, a JdV by Hyatt Hotel
Hotel
Nyack, NY, USA
9.5k from Pleasant Square center

Accommodations, Pools, Parking, Romantic, Pet-friendly, 4-star, Lodgings, Hot tubs, Places to stay

8.1

Very Good

756 reviews

$336
Average price / night
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Double Guestroom Stay | Steps to Hudson Riverwalk, Dining & Scenic Trails
Double Guestroom Stay | Steps to Hudson Riverwalk, Dining & Scenic Trails
Hotel
Ossining, NY, 10562, United States
3.1k from Pleasant Square center

AC, Arcade, Breakfast Available, Elevator, Fitness Equipment, Free Parking, Heater, Internet, No Smoking

New to Booking
$285
Average price / night
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West Gate Inn Nyack
West Gate Inn Nyack
Hotel
Nyack, NY, USA
9.6k from Pleasant Square center

Accommodations, Parking, Lodgings, Places to stay, Accessible hotels

6.6

Good

845 reviews

$123
Average price / night
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Serene Queen Guestroom Near Tivoli & Farm Markets
Serene Queen Guestroom Near Tivoli & Farm Markets
Hotel
Ossining, NY, 10562, United States
3.1k from Pleasant Square center

AC, Arcade, Breakfast Available, Elevator, Fitness Equipment, Free Parking, Heater, Internet, No Smoking

New to Booking
$269
Average price / night
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FairBridge Inn Express Nyack
FairBridge Inn Express Nyack
Hotel
Nyack, NY, USA
9.8k from Pleasant Square center

Accommodations, Parking, Lodgings, Places to stay, Accessible hotels

7.2

Good

232 reviews

$120
Average price / night
Check Availability
Minutes to Kayak Rentals, Trails & Picnic Spots | Double Guest room
Minutes to Kayak Rentals, Trails & Picnic Spots | Double Guest room
Hotel
Ossining, NY, 10562, United States
3.1k from Pleasant Square center

AC, Arcade, Breakfast Available, Elevator, Fitness Equipment, Free Parking, Heater, Internet, No Smoking

New to Booking
$285
Average price / night
Check Availability
2 Bright Double Rooms | Near Local Dining and Shopping at Palisades Center
2 Bright Double Rooms | Near Local Dining and Shopping at Palisades Center
Hotel
Ossining, NY, 10562, United States
3.1k from Pleasant Square center

AC, Arcade, Breakfast Available, Elevator, Fitness Equipment, Free Parking, Heater, Internet, No Smoking

New to Booking
$570
Average price / night
Check Availability
2 Comfortable Double Rooms | Near Historic Sites, Markets & Local Wineries
2 Comfortable Double Rooms | Near Historic Sites, Markets & Local Wineries
Hotel
Ossining, NY, 10562, United States
3.1k from Pleasant Square center

AC, Arcade, Breakfast Available, Elevator, Fitness Equipment, Free Parking, Heater, Internet, No Smoking

New to Booking
$570
Average price / night
Check Availability
Close to Historic Sites, Markets & Local Wineries | 3 Comfortable Double Rooms
Close to Historic Sites, Markets & Local Wineries | 3 Comfortable Double Rooms
Hotel
Ossining, NY, 10562, United States
3.1k from Pleasant Square center

AC, Arcade, Breakfast Available, Elevator, Fitness Equipment, Free Parking, Heater, Internet, No Smoking

New to Booking
$862
Average price / night
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Close to Art Studios & Hudson Nightlife | 3 Inviting Double Guestrooms
Close to Art Studios & Hudson Nightlife | 3 Inviting Double Guestrooms
Hotel
Ossining, NY, 10562, United States
3.1k from Pleasant Square center

AC, Arcade, Breakfast Available, Elevator, Fitness Equipment, Free Parking, Heater, Internet, No Smoking

New to Booking
$862
Average price / night
Check Availability
Relax in 4 Double Guestrooms Near Warren Street Shops & Waterfront Parks
Relax in 4 Double Guestrooms Near Warren Street Shops & Waterfront Parks
Hotel
Ossining, NY, 10562, United States
3.1k from Pleasant Square center

AC, Arcade, Breakfast Available, Elevator, Fitness Equipment, Free Parking, Heater, Internet, No Smoking

New to Booking
$1150
Average price / night
Check Availability
4 Comfortable Double Rooms | Close to Waterfront Music, Events & Breweries
4 Comfortable Double Rooms | Close to Waterfront Music, Events & Breweries
Hotel
Ossining, NY, 10562, United States
3.1k from Pleasant Square center

AC, Arcade, Breakfast Available, Elevator, Fitness Equipment, Free Parking, Heater, Internet, No Smoking

New to Booking
$1150
Average price / night
Check Availability
Queen Room | Minutes to Warren Street Boutiques & Local Dining
Queen Room | Minutes to Warren Street Boutiques & Local Dining
Hotel
Ossining, NY, 10562, United States
3.1k from Pleasant Square center

AC, Arcade, Breakfast Available, Elevator, Fitness Equipment, Free Parking, Heater, Internet, No Smoking

New to Booking
$269
Average price / night
Check Availability
Holiday Inn Express & Suites Hawthorne Elmsford North by IHG
Holiday Inn Express & Suites Hawthorne Elmsford North by IHG
Hotel
20 Saw Mill River Rd., Hawthorne, NY, 10532, United States
8.5k from Pleasant Square center

AC, Breakfast Included, Business Services, Elevator, Fitness Equipment, Free Parking, Frontdesk 24 Hour, Housekeeping, Internet

9.0

Fabulous

1005 reviews

$158
Average price / night
Check Availability

Pro Tip:
VacationByOwnerRentals 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 Hotels in Pleasant Square.

Pleasant Square Hotels on the Map

Frequently Asked Questions

You can explore 29 verified hotels in Pleasant Square. These include a range of options from luxury resorts and boutique hotels to budget-friendly accommodations suitable for different travel styles.

Hotel prices in Pleasant Square vary depending on the season, location, and property type. Rates typically start from around $120 per night, with higher prices for premium hotels, central locations, or peak travel dates.

Most hotels in Pleasant Square include amenities such as Wheelchair Accessible, Accessibility, and Guest Services. Additional features like breakfast, parking, or resort facilities may vary by property, so it’s helpful to review the details before booking.

You can identify top-rated hotels in Pleasant Square by sorting listings based on guest ratings and reviews. Looking at recent feedback, overall scores, and review volume can help you find properties that consistently deliver a high-quality experience.

For popular travel periods or busy locations, booking 30 to 60 days in advance is generally recommended to secure preferred options. During quieter periods, you may find more flexibility and availability closer to your travel dates.

Yes, some hotels in Pleasant Square welcome pets. Currently, 1 listings allow pets, although policies may vary. It’s a good idea to review any pet-related rules before booking.

Many hotels in Pleasant Square offer flexible or refundable booking options. Checking the cancellation policy before confirming your reservation can help you choose a rate that suits your travel plans.