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Find hotels near Pleasant Square, Ossining from $112

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Oct 30 - Nov 1
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Our top choices for Pleasant Square hotels

A spacious indoor area with large windows, modern furniture, and a view of a landscaped outdoor area.

1. Windrose On Hudson

Windrose On Hudson
3.0 star property
1.9 mi from Pleasant Square
8.6 out of 10, Excellent, (273 reviews)
"We had a wonderful stay at the Windrose on Hudson!! What a beautiful place! The facilities are very nice and the grounds are amazing!"
United States
Margaret
$164 nightly
The price is $183
Nov 8 - Nov 9
Total with taxes and fees
Windrose On Hudson
Indoor pool

2. DoubleTree by Hilton Hotel Nanuet

DoubleTree by Hilton Hotel Nanuet
4.0 star property
8.5 mi from Pleasant Square
9.0 out of 10, Wonderful, (1,186 reviews)
"Friendly helpful staff. Clean room with very comfortable bed. Wonderful restaurant food."
United States
Barbara
$129 nightly
The price is $150
Nov 22 - Nov 23
Total with taxes and fees
DoubleTree by Hilton Hotel Nanuet
A spacious hotel lobby with a modern design, featuring a large seating area, a dining table, and large windows providing views of the outdoors.

3. Element by Marriott Spring Valley

Element by Marriott Spring Valley
3.0 star property
9.2 mi from Pleasant Square
9.0 out of 10, Wonderful, (551 reviews)
"The room was clean (except for our kitchen sink which they came back and cleaned), spacious and beds were comfortable. We enjoyed the 24hr tea and coffee, the gym and breakfast also! Would definitely stay again."
United States
Danielle
$134 nightly
The price is $156
Nov 22 - Nov 23
Total with taxes and fees
Element by Marriott Spring Valley
An outdoor seating area with wicker chairs and tables, surrounded by greenery and a modern lamp structure.

4. Westchester Marriott

Westchester Marriott
4.5 star property
7.3 mi from Pleasant Square
8.8 out of 10, Excellent, (681 reviews)
"Great stay, clean and close to Sleepy Hollow. Would return again!"
United States
Karrie
$179 nightly
The price is $205
Nov 22 - Nov 23
Total with taxes and fees
Westchester Marriott
A modern hotel lobby with a kitchen area, seating arrangements, and large windows offering a view of the outdoors.

5. Baymont by Wyndham White Plains - Elmsford

Baymont by Wyndham White Plains - Elmsford
2.5 star property
6.7 mi from Pleasant Square
8.2 out of 10, Very good, (1,897 reviews)
"Really close to everything to do in Sleepy Hollow for a great price and very nice!"
United States
Amanda
$131 nightly
The price is $150
Nov 8 - Nov 9
Total with taxes and fees
Baymont by Wyndham White Plains - Elmsford
A buffet with various food items, including omelets and baked goods, served in metal containers.

6. Holiday Inn Express & Suites Peekskill-Lower Hudson Valley by IHG

Holiday Inn Express & Suites Peekskill-Lower Hudson Valley by IHG
2.5 star property
8.9 mi from Pleasant Square
9.2 out of 10, Wonderful, (1,004 reviews)
"Very clean, great staff, great breakfast."
United States
John
$127 nightly
The price is $145
Nov 22 - Nov 23
Total with taxes and fees
Holiday Inn Express & Suites Peekskill-Lower Hudson Valley by IHG
A modern bar area with a bar counter, multiple stools, and a seating area with a sofa and chairs.

7. Hotel Nyack, a JdV by Hyatt Hotel

Hotel Nyack, a JdV by Hyatt Hotel
4.0 star property
5.9 mi from Pleasant Square
8.6 out of 10, Excellent, (1,321 reviews)
"Nice hotel easy access from highway."
United States
Liana
$130 nightly
The price is $148
Nov 22 - Nov 23
Total with taxes and fees
Hotel Nyack, a JdV by Hyatt Hotel
A modern kitchen with a central island, bar stools, a fireplace, and a contemporary pendant light.

8. Courtyard by Marriott Tarrytown Westchester County

Courtyard by Marriott Tarrytown Westchester County
3.0 star property
6.8 mi from Pleasant Square
9.0 out of 10, Wonderful, (1,000 reviews)
"Very clean property with pleasant staff."
United States
Syble
$152 nightly
The price is $174
Nov 15 - Nov 16
Total with taxes and fees
Courtyard by Marriott Tarrytown Westchester County
A modern lobby with seating areas, a fireplace, and a flat-screen TV mounted on the wall.

9. Cambria Hotel & Suites - White Plains Downtown

Cambria Hotel & Suites - White Plains Downtown
3.5 star property
10.2 mi from Pleasant Square
9.4 out of 10, Exceptional, (1,007 reviews)
"Very conveniently located hotel, and great service"
United States
Anthony
$191 nightly
The price is $219
Nov 22 - Nov 23
Total with taxes and fees
Cambria Hotel & Suites - White Plains Downtown
A hotel patio with outdoor seating, a fire pit, and a covered area with glass doors.

10. Residence Inn Orangeburg

Residence Inn Orangeburg
3.0 star property
9.5 mi from Pleasant Square
8.8 out of 10, Excellent, (1,003 reviews)
"Great property!! Great staff!! Clean and lots of room!!"
United States
KAREN
$148 nightly
The price is $164
Nov 8 - Nov 9
Total with taxes and fees
Residence Inn Orangeburg
A hotel room with a wooden headboard, a bedside table with a lamp, and a bed with white bedding and pillows.

11. Ardsley Acres Hotel Westchester

Ardsley Acres Hotel Westchester
2.0 star property
10.6 mi from Pleasant Square
8.8 out of 10, Excellent, (1,250 reviews)
"Great Stay"
United States
Wendell
$132 nightly
The price is $151
Nov 12 - Nov 13
Total with taxes and fees
Ardsley Acres Hotel Westchester
A spacious lobby with a reception desk, sofas, and a coffee table. There are multiple seating areas and a large window providing natural light.

12. Sheraton Tarrytown Hotel

Sheraton Tarrytown Hotel
3.5 star property
7.1 mi from Pleasant Square
8.4 out of 10, Very good, (1,000 reviews)
"Nice stay"
United States
Kerry-Anna
$135 nightly
The price is $155
Nov 22 - Nov 23
Total with taxes and fees
Sheraton Tarrytown Hotel
A hotel room with a wooden desk, a green chair, a gray sofa, a kitchenette, and a door with a sign.

13. Hampton Inn Nanuet

Hampton Inn Nanuet
2.5 star property
9.4 mi from Pleasant Square
8.2 out of 10, Very good, (1,000 reviews)
"A blessed stay overall."
United States
Leonard
$106 nightly
The price is $123
Nov 4 - Nov 5
Total with taxes and fees
Hampton Inn Nanuet
A spacious lobby with a red sofa, green armchairs, a fireplace, and a staircase leading to an upper level.

14. Hotel MTK Mount Kisco

Hotel MTK Mount Kisco
3.0 star property
8.2 mi from Pleasant Square
8.6 out of 10, Excellent, (1,000 reviews)
"This hotel served our purposes very well."
United States
Joseph
$144 nightly
The price is $165
Nov 4 - Nov 5
Total with taxes and fees
Hotel MTK Mount Kisco
An outdoor seating area with modern furniture, a fire pit, and ambient lighting.

15. Sonesta White Plains Downtown

Sonesta White Plains Downtown
4.0 star property
10.5 mi from Pleasant Square
9.0 out of 10, Wonderful, (1,359 reviews)
"Well, maintained property and great location!"
United States
Laura
$175 nightly
The price is $200
Nov 22 - Nov 23
Total with taxes and fees
Sonesta White Plains Downtown
A modern reception area with a wooden reception desk, a blue accent wall, and a large glass door leading to an outdoor seating area.

16. Holiday Inn Express & Suites Hawthorne Elmsford North by IHG

Holiday Inn Express & Suites Hawthorne Elmsford North by IHG
2.5 star property
5.3 mi from Pleasant Square
8.8 out of 10, Excellent, (1,000 reviews)
"Great stay"
United States
Sean P.
$144 nightly
The price is $165
Nov 15 - Nov 16
Total with taxes and fees
Holiday Inn Express & Suites Hawthorne Elmsford North by IHG
A modern hotel lobby with a dining area, seating, and a large window offering a view of greenery.

17. Hilton Garden Inn Westchester Dobbs Ferry, NY

Hilton Garden Inn Westchester Dobbs Ferry, NY
3.0 star property
11 mi from Pleasant Square
8.4 out of 10, Very good, (1,000 reviews)
"Room was clean and staff were super friendly. Amenities were what you would expect from a great hotel, no complaints on this end !"
United States
Mustafa
$135 nightly
The price is $155
Nov 22 - Nov 23
Total with taxes and fees
Hilton Garden Inn Westchester Dobbs Ferry, NY
A checkered floor, a potted plant, and two metal ladders in a room with large windows.

18. West Gate Inn Nyack

West Gate Inn Nyack
3.0 star property
5.9 mi from Pleasant Square
7.4 out of 10, Good, (1,503 reviews)
"It was a great stay. Hotel was well equipped and came with lovely breakfast."
United States
Stuart
$98 nightly
The price is $112
Nov 8 - Nov 9
Total with taxes and fees
West Gate Inn Nyack
A hotel entrance with a sign reading "SONESTA Simply Suites".

19. Sonesta Simply Suites Nanuet

Sonesta Simply Suites Nanuet
2.5 star property
9.4 mi from Pleasant Square
8.4 out of 10, Very good, (1,227 reviews)
"Good location & acceptable for a convenient overnight while traveling."
United States
Susan
$117 nightly
The price is $136
Nov 12 - Nov 13
Total with taxes and fees
Sonesta Simply Suites Nanuet
A historic stone building with a turret, arched entrance, and a covered patio area.

20. Tarrytown House Estate

Tarrytown House Estate
3.5 star property
7.8 mi from Pleasant Square
8.2 out of 10, Very good, (1,397 reviews)
"Beautiful property, great breakfast and restaurant on site, and friendly and helpful staff."
United States
Michael
$180 nightly
The price is $206
Nov 24 - Nov 25
Total with taxes and fees
Tarrytown House Estate
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties

Compare popular hotels close to Pleasant Square

Property
Star rating
Guest rating
Breakfast included
Pool
Spa
Pet friendly
WiFi included
A spacious indoor area with large windows, modern furniture, and a view of a landscaped outdoor area.
Windrose On Hudson
3.0 star property
8.6
Excellent
273 reviews
View
Indoor pool
DoubleTree by Hilton Hotel Nanuet
4.0 star property
9.0
Wonderful
1,186 reviews
View
A spacious hotel lobby with a modern design, featuring a large seating area, a dining table, and large windows providing views of the outdoors.
Element by Marriott Spring Valley
3.0 star property
9.0
Wonderful
551 reviews
View
An outdoor seating area with wicker chairs and tables, surrounded by greenery and a modern lamp structure.
Westchester Marriott
4.5 star property
8.8
Excellent
681 reviews
View
A modern hotel lobby with a kitchen area, seating arrangements, and large windows offering a view of the outdoors.
Baymont by Wyndham White Plains - Elmsford
2.5 star property
8.2
Very good
1,897 reviews
View

Top Pleasant Square Hotel Reviews

Pod Times Square

Pod Times Square

10/10 Excellent
"Clean rooms and friendly staff"
Juliana 1-night trip
Posted 1 hour ago
Pod Times Square

Other attractions near Pleasant Square

Merchants Square

9.0/10 (2 reviews)
Explore the great outdoors at Merchants Square, a lovely green space in Ossining. Stroll along the riverfront or attend a sporting event in this quaint area.
See properties

Frequently asked questions

What's the area like around Pleasant Square?
Pleasant Square is located in a family-friendly area of Ossining known for its array of dining options and hiking. You'll find 36 hotels and other accommodations within a few miles for a convenient home base.
Where is the best place to stay close to Pleasant Square?
Radio Hotel is one of the top choices for your stay based on our traveler data, and this hotel offers a restaurant and a 24-hour fitness center. You'll find it 22 mi (35.5 km) from Pleasant Square. Other good options around the area include Night Hotel Broadway and Hotel Belleclaire Central Park, a Small Luxury Hotel.
How many hotels can I expect to find near Pleasant Square?
Expedia has 36 hotels and other accommodations a few miles from Pleasant Square.
If I need to cancel the hotel reservation for my stay near Pleasant Square, will I receive a refund?
Yes, you'll find most room reservations are fully refundable if you cancel prior to the hotel's cancellation deadline, which is usually within 24-48 hours of your arrival date. If your reservation is non-refundable, you might be able to cancel it and receive a refund within a 24-hour period of booking. Add your dates and click on "Search", then you can filter by "fully refundable" to review top deals close to Pleasant Square.
Where can I learn more about changing or cancelling my trip in the area near Pleasant Square?
For additional details about updating your stay near Pleasant Square or cancelling it, go to https://www.expedia.com/service/.
What can I see and do near Pleasant Square?
You'll want to browse the exhibits at Sing Sing Prison Museum and Ossining Historical Society. Van Cortlandt Manor, Sleepy Hollow Cemetery, and Old Dutch Church of Sleepy Hollow are some of the local landmarks to explore. Consider spending a leisurely afternoon outside at Croton Point Park, Rockland Lake State Park, or Louis Engel Waterfront Park.

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