Find hotels near Pleasant Square, Ossining from $123

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Compare 8,759 hotels close to Pleasant Square with room rates, reviews, and availability. Most hotels are fully refundable.

Terrace/patio
Windrose On Hudson

Windrose On Hudson

3.0 star property
1.9 mi from Pleasant Square
8.0 out of 10, Very Good, (78)
"Nice place to stay, very quiet and comfortable."
United States
Mariano
$177 nightly
The price is $198
Dec 3 - Dec 4
Total with taxes and fees
Windrose On Hudson
House | 5 bedrooms
Foliage at Westchester Manor - Near Sleepy Hollow

Foliage at Westchester Manor - Near Sleepy Hollow

2.0 star property
0.4 mi from Pleasant Square
$782 nightly
The price is $870
Nov 16 - Nov 17
Total with taxes and fees
Foliage at Westchester Manor - Near Sleepy Hollow
Property amenity
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, (1004)
"Our stay was very cozy and comfortable. Our room was clean and had a great view. Conveniently located for our plans. Would recommend "
United States
Donald
$149 nightly
The price is $170
Nov 30 - Dec 1
Total with taxes and fees
Courtyard by Marriott Tarrytown Westchester County
Exterior
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, (934)
"Great hotel to enjoy all the SleepHollow excursions. "
United States
Michelle
$169 nightly
The price is $193
Dec 8 - Dec 9
Total with taxes and fees
Holiday Inn Express & Suites Hawthorne Elmsford North by IHG
Lobby
Cambria Hotel White Plains - Downtown

Cambria Hotel White Plains - Downtown

3.5 star property
10.2 mi from Pleasant Square
9.4 out of 10, Exceptional, (1004)
"Big rooms great amenities and location!"
United States
Evan
$187 nightly
The price is $214
Dec 7 - Dec 8
Total with taxes and fees
Cambria Hotel White Plains - Downtown
Exterior
The Abbey Inn & Spa

The Abbey Inn & Spa

4.0 star property
9.7 mi from Pleasant Square
9.2 out of 10, Wonderful, (215)
"Great quaint hotel "
United States
tsontcho
$304 nightly
The price is $348
Nov 16 - Nov 17
Total with taxes and fees
The Abbey Inn & Spa
Reception
Westchester Marriott

Westchester Marriott

4.5 star property
7.3 mi from Pleasant Square
8.8 out of 10, Excellent, (421)
"Everyone was helpful, pleasant. Excellent staff working at that location"
United States
LAURA DIANE
$186 nightly
The price is $213
Dec 4 - Dec 5
Total with taxes and fees
Westchester Marriott
Lobby
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, (1006)
"The bathroom/shower was very spacious and the bed very comfortable. Great place to stay!"
United States
Lawrence
$123 nightly
The price is $140
Nov 25 - Nov 26
Total with taxes and fees
Hotel Nyack, a JdV by Hyatt Hotel
Exterior
The Opus Westchester, Autograph Collection

The Opus Westchester, Autograph Collection

5.0 star property
10.2 mi from Pleasant Square
9.2 out of 10, Wonderful, (524)
"our room was very clean on beds very comfortable staff friendly, breakfast wonderful"
United States
Susan
$349 nightly
The price is $399
Nov 20 - Nov 21
Total with taxes and fees
The Opus Westchester, Autograph Collection
Lobby
DoubleTree by Hilton Hotel Nanuet

DoubleTree by Hilton Hotel Nanuet

4.0 star property
8.5 mi from Pleasant Square
8.8 out of 10, Excellent, (1004)
"Very clean very beautiful very good hospitality would stay again"
United States
Bobby
$106 nightly
The price is $123
Nov 30 - Dec 1
Total with taxes and fees
DoubleTree by Hilton Hotel Nanuet
Lobby
Element Spring Valley

Element Spring Valley

3.0 star property
9.2 mi from Pleasant Square
8.8 out of 10, Excellent, (426)
"Staff, cleanliness, nice breakfast"
United States
Jesus
$134 nightly
The price is $156
Nov 16 - Nov 17
Total with taxes and fees
Element Spring Valley
View from property
Residence Inn Orangeburg

Residence Inn Orangeburg

3.0 star property
9.5 mi from Pleasant Square
8.8 out of 10, Excellent, (1001)
"Great staff, great location "
United States
Luis
$152 nightly
The price is $169
Nov 23 - Nov 24
Total with taxes and fees
Residence Inn Orangeburg
Exterior
SpringHill Suites by Marriott Tarrytown Westchester County

SpringHill Suites by Marriott Tarrytown Westchester County

3.0 star property
6.9 mi from Pleasant Square
8.4 out of 10, Very Good, (1004)
"Staff were awesome"
United States
Terry
$152 nightly
The price is $174
Nov 23 - Nov 24
Total with taxes and fees
SpringHill Suites by Marriott Tarrytown Westchester County
Free daily self-serve breakfast
Holiday Inn Express Hotel & Suites Peekskill -Lower Hudson Valley by IHG

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

2.5 star property
8.9 mi from Pleasant Square
9.2 out of 10, Wonderful, (1003)
"Quick check in, and efficient and friendly staff. "
United States
Julissa
$127 nightly
The price is $145
Nov 30 - Dec 1
Total with taxes and fees
Holiday Inn Express Hotel & Suites Peekskill -Lower Hudson Valley by IHG
Indoor pool, sun loungers
Sonesta White Plains Downtown

Sonesta White Plains Downtown

4.0 star property
10.5 mi from Pleasant Square
8.8 out of 10, Excellent, (1112)
"Clean next to the mall great gor food and restaurants "
United States
michelle
$197 nightly
The price is $225
Nov 23 - Nov 24
Total with taxes and fees
Sonesta White Plains Downtown
Free daily self-serve breakfast
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, (1446)
"The rooms and the hospitality was amazing."
United States
Debra
$130 nightly
The price is $149
Nov 17 - Nov 18
Total with taxes and fees
Baymont by Wyndham White Plains - Elmsford
Interior entrance
Hotel MTK Mount Kisco

Hotel MTK Mount Kisco

3.0 star property
8.2 mi from Pleasant Square
8.4 out of 10, Very Good, (1001)
"Excellent hotel. "
United States
Samuel
$155 nightly
The price is $177
Nov 17 - Nov 18
Total with taxes and fees
Hotel MTK Mount Kisco
Exterior
Sheraton Tarrytown Hotel

Sheraton Tarrytown Hotel

3.5 star property
7.1 mi from Pleasant Square
8.2 out of 10, Very Good, (1006)
"Great place "
United States
Michael
$144 nightly
The price is $164
Nov 23 - Nov 24
Total with taxes and fees
Sheraton Tarrytown Hotel
Exterior
Residence Inn by Marriott White Plains Westchester County

Residence Inn by Marriott White Plains Westchester County

3.0 star property
10 mi from Pleasant Square
8.6 out of 10, Excellent, (646)
"Staff very helpful "
United States
Bianca
$202 nightly
The price is $231
Nov 30 - Dec 1
Total with taxes and fees
Residence Inn by Marriott White Plains Westchester County
Premium bedding, desk, iron/ironing board, free WiFi
Ardsley Acres Hotel Westchester

Ardsley Acres Hotel Westchester

2.0 star property
10.6 mi from Pleasant Square
8.6 out of 10, Excellent, (1014)
"Omg the rooms of this hotel are amazing and cute"
United States
Abdele
$130 nightly
The price is $149
Nov 11 - Nov 12
Total with taxes and fees
Ardsley Acres Hotel Westchester
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.
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Hotels close to Pleasant Square with a pool

House | 5 bedrooms
Foliage at Westchester Manor - Near Sleepy Hollow
Foliage at Westchester Manor - Near Sleepy Hollow
2.0 star property
  • Pool
$782 nightly
The price is $870
Nov 16 - Nov 17
Total with taxes and fees
Foliage at Westchester Manor - Near Sleepy Hollow
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Top guest rated hotels close to Pleasant Square

Terrace/patio
Windrose On Hudson
Windrose On Hudson
3.0 star property
    8.0 out of 10, Very Good, (78)
    $177 nightly
    The price is $198
    Dec 3 - Dec 4
    Total with taxes and fees
    Windrose On Hudson
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    Top Pleasant Square Hotel Reviews

    Lotte New York Palace

    Lotte New York Palace

    10/10 Excellent
    "Good"
    hector 1-night trip
    Posted 15 hours ago
    Lotte New York Palace

    Hotels near other Pleasant Square attractions

    Merchants Square

    Explore the great outdoors at Merchants Square, a lovely green space in Ossining. Stroll along the riverfront or attend a sporting event in this family-friendly area.
    See properties

    Sing Sing Prison Museum

    You can spend time browsing the exhibits at Sing Sing Prison Museum during your travels in Ossining. Amble around this quaint area's riverfront and enjoy its top-notch restaurants.
    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 41 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 (35.4 km) from Pleasant Square. Other good options around the area include Night Hotel Broadway and Empire Hotel.
    How many hotels can I expect to find near Pleasant Square?
    Expedia has 41 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. Sing Sing Correctional Facility, Van Cortlandt Manor, and Sleepy Hollow Cemetery are some of the local landmarks to explore. Consider spending a leisurely afternoon outside at Croton Point Park, Rockland Lake State Park, or Depot Square.

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