Hotels near Pleasant Square

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Top 10 Hotels Near Pleasant Square

Windrose On Hudson

2.0 star property
8.4 out of 10, Very good, (8)
"Staying the historic former GE Crottonville training center. The place is amazing. It wasn’t intended to be a hotel per se. It is way, way more than that. I think it is still looking for its footing as a hotel/corporate conference training center for public, so being able to stay here feels like I have a 6 Sigma training with Neutron Jack at 8:AM. The place is something to see for yourself hurry!!"
The price is RM1,055
RM1,175 total
includes taxes & fees
17 Aug - 18 Aug
Windrose On Hudson

Holiday Inn Express & Suites Hawthorne Elmsford North by IHG

2.5 star property
8.8 out of 10, Excellent, (844)
"the beds were very comfortable, "
The price is RM843
RM964 total
includes taxes & fees
11 Aug - 12 Aug
Holiday Inn Express & Suites Hawthorne Elmsford North by IHG

Courtyard by Marriott Tarrytown Westchester County

3.0 star property
9.0 out of 10, Wonderful, (1001)
"Nice hotel"
The price is RM682
RM780 total
includes taxes & fees
17 Aug - 18 Aug
Courtyard by Marriott Tarrytown Westchester County

Hotel Nyack, a JdV by Hyatt Hotel

4.0 star property
8.6 out of 10, Excellent, (1005)
"This is a fun property for a friends or couples getaway in the summer because the pool and bar service were on point…walkable to a cute little town with bars and restaurants. Rooms are comfortable and spacious. Staff is super friendly! "
The price is RM419
RM595 total
includes taxes & fees
19 Aug - 20 Aug
Hotel Nyack, a JdV by Hyatt Hotel

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

2.5 star property
9.2 out of 10, Wonderful, (1001)
"Would stay again"
The price is RM644
RM737 total
includes taxes & fees
19 Aug - 20 Aug
Holiday Inn Express Hotel & Suites Peekskill -Lower Hudson Valley by IHG

Westchester Marriott

4.5 star property
8.8 out of 10, Excellent, (330)
"Great stay - would def stay there again!"
The price is RM709
RM811 total
includes taxes & fees
17 Aug - 18 Aug
Westchester Marriott

The Abbey Inn & Spa

4.0 star property
9.2 out of 10, Wonderful, (192)
"This place is amazing. The site is heavenly, with views of the Hudson and a pool and trails. I wish the restaurant/ bar were open later. But really, the place was perfect. "
The price is RM1,197
RM1,563 total
includes taxes & fees
19 Aug - 20 Aug
The Abbey Inn & Spa

The Opus Westchester, Autograph Collection

5.0 star property
9.2 out of 10, Wonderful, (503)
"Although I stayed for 1 night, I wish my stay was a little longer. This hotel exceeds my expectations. I had a wonderful time and stay. The spa was so beautiful and amazing. I would definitely recommend this hotel. "
The price is RM1,352
RM1,546 total
includes taxes & fees
17 Aug - 18 Aug
The Opus Westchester, Autograph Collection

DoubleTree by Hilton Hotel Nanuet

4.0 star property
8.8 out of 10, Excellent, (1006)
"Comfortable bed, nice bathroom, great staff!"
The price is RM537
RM624 total
includes taxes & fees
1 Sept - 2 Sept
DoubleTree by Hilton Hotel Nanuet

SpringHill Suites by Marriott Tarrytown Westchester County

3.0 star property
8.4 out of 10, Very good, (1002)
"Thank you nice visit "
The price is RM717
RM820 total
includes taxes & fees
17 Aug - 18 Aug
SpringHill Suites by Marriott Tarrytown Westchester County

Element Spring Valley

3.0 star property
8.8 out of 10, Excellent, (385)
"Great stay. Very clean and spacious rooms, with a convenient breakfast offered every morning. "
The price is RM648
RM754 total
includes taxes & fees
31 Aug - 1 Sept
Element Spring Valley

Baymont by Wyndham White Plains - Elmsford

2.5 star property
8.2 out of 10, Very good, (1392)
"Good place to stay "
The price is RM609
RM696 total
includes taxes & fees
17 Aug - 18 Aug
Baymont by Wyndham White Plains - Elmsford

Residence Inn Orangeburg

3.0 star property
8.8 out of 10, Excellent, (1005)
"Good place "
The price is RM651
RM725 total
includes taxes & fees
10 Aug - 11 Aug
Residence Inn Orangeburg

Sheraton Tarrytown Hotel

3.5 star property
8.2 out of 10, Very good, (1007)
"Nice property for family staying "
The price is RM609
RM696 total
includes taxes & fees
17 Aug - 18 Aug
Sheraton Tarrytown Hotel

Hotel MTK Mount Kisco

3.0 star property
8.4 out of 10, Very good, (1002)
"Proximity to Mt. Kisco is great!"
The price is RM651
RM745 total
includes taxes & fees
10 Aug - 11 Aug
Hotel MTK Mount Kisco

Residence Inn by Marriott White Plains Westchester County

3.0 star property
8.6 out of 10, Excellent, (619)
"Excellent service and rooms"
The price is RM804
RM920 total
includes taxes & fees
24 Aug - 25 Aug
Residence Inn by Marriott White Plains Westchester County

Hampton Inn White Plains/Tarrytown

3.0 star property
8.0 out of 10, Very good, (1095)
"Easy check in and breakfast was amazing"
The price is RM580
RM663 total
includes taxes & fees
17 Aug - 18 Aug
Hampton Inn White Plains/Tarrytown

Sonesta Simply Suites Nanuet

2.5 star property
8.4 out of 10, Very good, (1006)
"It a clean, quiet, and convenient place. Great for families."
The price is RM454
RM528 total
includes taxes & fees
31 Aug - 1 Sept
Sonesta Simply Suites Nanuet

Tarrytown House Estate

3.5 star property
8.0 out of 10, Very good, (1002)
"This has been our go to for years! A beautiful property with great dining options nearby and activities! "
The price is RM675
RM858 total
includes taxes & fees
6 Aug - 7 Aug
Tarrytown House Estate

Sonesta White Plains Downtown

4.0 star property
8.6 out of 10, Excellent, (1095)
"Lovely and comfortable hotel. Highly recommend staying here. "
The price is RM679
RM899 total
includes taxes & fees
1 Sept - 2 Sept
Sonesta White Plains Downtown
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Top Pleasant Square Hotel Reviews

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 34 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 traveller data, and this hotel offers a restaurant and a 24-hour fitness centre. You'll find it 22 mi (35.4 km) from Pleasant Square. Other good options around the area include Night Hotel Broadway and La Quinta Inn & Suites by Wyndham Secaucus Meadowlands.

How many hotels should I expect to find near Pleasant Square?

Expedia has 34 hotels and other accommodation options 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, most hotel room reservations are refundable if you cancel prior to the hotel's cancellation deadline, which is often 24 or 48 hours before check in. If you have a non-refundable reservation, you might still have the option to cancel and receive a refund within 24 hours of booking. Plug in your dates, click on "Search", then filter by "fully refundable" to get the best deals near Pleasant Square.

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, Rockefeller State Park Preserve or Rockland Lake State Park.