Search Resort Hotels in Pleasantville from CA $102

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
Nov 13 - Nov 15
In two weeks
Nov 20 - Nov 22
In one month
Dec 4 - Dec 6
In two months
Jan 1 - Jan 3
No exact matches found, but these alternatives could be just right

Recommended hotels in Pleasantville

A modern reception area with a wooden reception desk, a blue accent wall, and a large glass door leading to an outdoor seating area.

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

Holiday Inn Express & Suites Hawthorne Elmsford North by IHG
2.5 star property
Hawthorne
9.0 out of 10, Wonderful, (1,001 reviews)
"Great stay"
United States
Sean P.
The price is CA $172
CA $197 total
includes taxes & fees
Dec 6 - Dec 7
Holiday Inn Express & Suites Hawthorne Elmsford North by IHG
A modern hotel lobby with a kitchen area, seating arrangements, and large windows offering a view of the outdoors.

2. Baymont by Wyndham White Plains - Elmsford

Baymont by Wyndham White Plains - Elmsford
2.5 star property
Elmsford
8.2 out of 10, Very good, (1,890 reviews)
"Went for Halloween weekend it was very nice pool was nice as well there a Dunkin’ 3 min walking distance and a 7 min drive to tarry town it was wonderful"
United States
Omari
The price is CA $185
CA $212 total
includes taxes & fees
Nov 29 - Nov 30
Baymont by Wyndham White Plains - Elmsford
A spacious lobby with a reception desk, sofas, and a coffee table. There are multiple seating areas and a large window providing natural light.

3. Sheraton Tarrytown Hotel

Sheraton Tarrytown Hotel
3.5 star property
Tarrytown
8.4 out of 10, Very good, (1,001 reviews)
"Nice stay"
United States
Kerry-Anna
The price is CA $189
CA $216 total
includes taxes & fees
Nov 22 - Nov 23
Sheraton Tarrytown Hotel
A modern kitchen with a large island, bar stools, a flat-screen TV, and a stone backsplash.

4. Hampton Inn White Plains/Tarrytown

Hampton Inn White Plains/Tarrytown
3.0 star property
Elmsford
7.8 out of 10, Good, (1,726 reviews)
"The room was pretty clean and comfortable, staff was friendly"
United States
Zack
The price is CA $158
CA $181 total
includes taxes & fees
Nov 22 - Nov 23
Hampton Inn White Plains/Tarrytown
A modern kitchen with a central island, bar stools, a fireplace, and a contemporary pendant light.

5. Courtyard by Marriott Tarrytown Westchester County

Courtyard by Marriott Tarrytown Westchester County
3.0 star property
Tarrytown
9.0 out of 10, Wonderful, (1,001 reviews)
"Very clean property with pleasant staff."
United States
Syble
The price is CA $212
CA $243 total
includes taxes & fees
Nov 19 - Nov 20
Courtyard by Marriott Tarrytown Westchester County
A spacious indoor area with large windows, modern furniture, and a view of a landscaped outdoor area.

6. Windrose On Hudson

Windrose On Hudson
3.0 star property
Ossining
8.6 out of 10, Excellent, (283 reviews)
"Would 100% stay again"
United States
Michael
The price is CA $211
CA $235 total
includes taxes & fees
Nov 15 - Nov 16
Windrose On Hudson
A hotel with a modern facade, a prominent signage for SpringHill Suites Marriott, and a covered entrance area with seating.

7. SpringHill Suites by Marriott Tarrytown Westchester County

SpringHill Suites by Marriott Tarrytown Westchester County
3.0 star property
Tarrytown
8.8 out of 10, Excellent, (1,006 reviews)
"Clean, friendly staff, would stay again"
United States
Gwen
The price is CA $218
CA $249 total
includes taxes & fees
Nov 15 - Nov 16
SpringHill Suites by Marriott Tarrytown Westchester County
An outdoor seating area with wicker chairs and tables, surrounded by greenery and a modern lamp structure.

8. Westchester Marriott

Westchester Marriott
4.5 star property
Tarrytown
8.8 out of 10, Excellent, (689 reviews)
"Great stay, clean and close to Sleepy Hollow. Would return again!"
United States
Karrie
The price is CA $250
CA $286 total
includes taxes & fees
Nov 22 - Nov 23
Westchester Marriott
A spacious room with a stone fireplace, white sofas, and a large window offering a view of the outdoors.

9. Sleepy Hollow Hotel, a Dolce by Wyndham

Sleepy Hollow Hotel, a Dolce by Wyndham
3.5 star property
Tarrytown
7.0 out of 10, Good, (1,000 reviews)
"Great stay"
United States
Brittany J.
The price is CA $186
CA $213 total
includes taxes & fees
Dec 1 - Dec 2
Sleepy Hollow Hotel, a Dolce by Wyndham
A breakfast area with multiple tables and chairs, a kitchen area with appliances, and a sign for Daybreak Breakfast.

10. Days Inn by Wyndham Elmsford / White Plains

Days Inn by Wyndham Elmsford / White Plains
2.0 star property
Elmsford
7.4 out of 10, Good, (1,030 reviews)
"Great place to stay, extremely friendly and helpful staff"
United States
Frankie
The price is CA $149
CA $170 total
includes taxes & fees
Nov 29 - Nov 30
Days Inn by Wyndham Elmsford / White Plains
A modern bar area with a bar counter, multiple stools, and a seating area with a sofa and chairs.

11. Hotel Nyack, a JdV by Hyatt Hotel

Hotel Nyack, a JdV by Hyatt Hotel
4.0 star property
Nyack
8.6 out of 10, Excellent, (1,329 reviews)
"Great stay!"
United States
Kristen
The price is CA $161
CA $222 total
includes taxes & fees
Dec 2 - Dec 3
Hotel Nyack, a JdV by Hyatt Hotel
A spacious lobby with a red sofa, green armchairs, a fireplace, and a staircase leading to an upper level.

12. Hotel MTK Mount Kisco

Hotel MTK Mount Kisco
3.0 star property
Mount Kisco
8.6 out of 10, Excellent, (1,001 reviews)
"This hotel served our purposes very well."
United States
Joseph
The price is CA $205
CA $235 total
includes taxes & fees
Nov 15 - Nov 16
Hotel MTK Mount Kisco
A historic stone building with a turret, arched entrance, and a covered patio area.

13. Tarrytown House Estate

Tarrytown House Estate
3.5 star property
Tarrytown
8.2 out of 10, Very good, (1,419 reviews)
"It was a beautiful place to stay"
United States
Brooke
The price is CA $278
CA $353 total
includes taxes & fees
Nov 8 - Nov 9
Tarrytown House Estate
A checkered floor, a potted plant, and two metal ladders in a room with large windows.

14. West Gate Inn Nyack

West Gate Inn Nyack
3.0 star property
Nyack
7.4 out of 10, Good, (1,509 reviews)
"Awesome place will still again if in area"
United States
Joshua
The price is CA $151
CA $173 total
includes taxes & fees
Nov 18 - Nov 19
West Gate Inn Nyack
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
White Plains
9.0 out of 10, Wonderful, (1,353 reviews)
"Well, maintained property and great location!"
United States
Laura
The price is CA $233
CA $313 total
includes taxes & fees
Nov 22 - Nov 23
Sonesta White Plains Downtown
A modern lobby with seating areas, a fireplace, and a flat-screen TV mounted on the wall.

16. Cambria Hotel & Suites - White Plains Downtown

Cambria Hotel & Suites - White Plains Downtown
3.5 star property
White Plains
9.2 out of 10, Wonderful, (1,005 reviews)
"Very conveniently located hotel, and great service"
United States
Anthony
The price is CA $267
CA $306 total
includes taxes & fees
Nov 29 - Nov 30
Cambria Hotel & Suites - White Plains Downtown
A spacious lobby with a seating area, a coffee station, and a staircase leading to an upper floor.

17. Tappan Zee Hotel

Tappan Zee Hotel
2.0 star property
West Nyack
6.6 out of 10, (791 reviews)
"The room was very adequate and the staff were more than helpful. I would stay there again without hesitation."
United States
Robert
The price is CA $103
CA $119 total
includes taxes & fees
Nov 6 - Nov 7
Tappan Zee Hotel
A modern high-rise hotel with a curved facade, multiple floors, and a well-lit entrance.

18. Residence Inn by Marriott White Plains Westchester County

Residence Inn by Marriott White Plains Westchester County
3.0 star property
White Plains
8.6 out of 10, Excellent, (760 reviews)
"Large rooms and daily breakfast with great variety. Within walking distance of downtown for shopping and restaurants."
United States
Cheryl Eileen Anderson
The price is CA $281
CA $321 total
includes taxes & fees
Nov 22 - Nov 23
Residence Inn by Marriott White Plains Westchester County
Indoor pool

19. DoubleTree by Hilton Hotel Nanuet

DoubleTree by Hilton Hotel Nanuet
4.0 star property
Nanuet
9.0 out of 10, Wonderful, (1,188 reviews)
"Great place"
United States
Joel
The price is CA $177
CA $206 total
includes taxes & fees
Nov 22 - Nov 23
DoubleTree by Hilton Hotel Nanuet
A spacious hotel dining area with a long table, multiple chairs, and modern pendant lighting.

20. Hampton Inn & Suites Yonkers - Westchester

Hampton Inn & Suites Yonkers - Westchester
2.5 star property
Northeast Yonkers
9.0 out of 10, Wonderful, (1,249 reviews)
"Nice property & friendly staff"
United States
Jeffrey
The price is CA $174
CA $205 total
includes taxes & fees
Nov 29 - Nov 30
Hampton Inn & Suites Yonkers - 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.
View all properties

Learn more about Pleasantville

This charming Westchester village offers a peaceful escape with its walkable downtown filled with independent shops and the Jacob Burns Film Centre. Grab a coffee at The Black Cow before exploring nearby Rockefeller State Park Preserve's scenic trails and stone bridges.

See all hotels in Pleasantville
A calm lake surrounded by autumn-colored trees reflecting in the water.

Top reviews in Pleasantville

A modern reception area with a wooden reception desk, a blue accent wall, and a large glass door leading to an outdoor seating area.
Holiday Inn Express & Suites Hawthorne Elmsford North by IHG

Holiday Inn Express & Suites Hawthorne Elmsford North by IHG

Holiday Inn Express & Suites Hawthorne Elmsford North by IHG
Hawthorne

10/10 Excellent

Room and all around the hotel was cleaned and kept clean throughout my stay. Staff were VERY welcoming and helpful and the free breakfast was a bonus & I can’t forget about their 24hr coffee machine, it is definitely worth the entire stay.
Canada
Kiarra
Reviewed August 6, 2026
Holiday Inn Express & Suites Hawthorne Elmsford North by IHG

Frequently Asked Questions

What can I expect from a resort vacation in Pleasantville?

Expedia can help you find resorts and other lodging options that have similar amenities and comforts. If you have trouble finding a resort in Pleasantville that works for you, you can use the search filters to look for hotels, or search for properties with amenities like pools or all-inclusive rates. We make it easy to book great accommodations so you can focus on planning your trip itinerary.

What's a favorite resort for my stay in Pleasantville?

Here's our top-rated resort near Pleasantville: CAM BLISS RETREAT, Only room for one🌹❤️. - 18.5 mi (29.7 km) from Pleasantville. Features a sauna.

What can I do in Pleasantville?

Experience the local theater scene at Jacob Burns Film Center Theater, or bring the kids to Jacob Burns Film Center Media Arts Lab for some family fun. In the area, other attractions include Rockefeller State Park Preserve and New York Medical College.

What's the weather like in Pleasantville?

The hottest months are usually July and August with an average temp of 71°F, while the coldest months are January and February with an average of 34°F. Average annual precipitation for Pleasantville is 51 inches.

What's the best way to get to and around Pleasantville?

Fly into Westchester County Airport (HPN), which is located 6.4 mi (10.3 km) away from the city center. You can also search for flights into Danbury, CT (DXR-Danbury Municipal), which is 22.9 mi (36.9 km) away. If you'd like to venture out around the area, consider renting a car to take in more sights.

Explore a world of travel with Expedia