Title: Pleasantville Vacation Packages & Trips 2026 from CA $1,051 | Expedia.ca [Pleasantville Travel Guide](https://expedia.ca/Pleasantville.dx9121)[Hotels in Pleasantville](https://expedia.ca/Pleasantville-Hotels.d9121.Travel-Guide-Hotels)[Vacation Rentals in Pleasantville](https://expedia.ca/Pleasantville-Vacation-Rentals.d9121.Travel-Guide-VacationRentals)[Pleasantville Car Rentals](https://expedia.ca/Car-Rentals-In-Pleasantville.d9121.Car-Rental-Guide) ![](https://images.trvl-media.com/place/9121/26cce5d1-ffdd-4ebc-9808-e49a83d15294.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Pleasantville Vacation Packages ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to CA $1,096 when you book a flight and hotel together\* - ### Find the right fit With over 300,000 hotels worldwide, it's easy to create a perfect package - ### Rest easy Plan, book, and manage your trip all in one place #### Your Pleasantville Vacation When you book a vacation package to Pleasantville, you can relax and enjoy your getaway knowing that all your travel plans are under control. Discover the many charms of this city while staying in a neighborhood like Montrose, which is great for walking. A trip to Pleasantville is a terrific opportunity to go sightseeing. Be sure to look around renowned attractions like [Tarrytown Music Hall](https://www.expedia.ca/Tarrytown-Music-Hall-Tarrytown.d6211022.Vacation-Attraction), [Van Cortlandt Manor](https://www.expedia.ca/Van-Cortlandt-Manor-Croton-on-Hudson.d6207691.Vacation-Attraction) and [Sing Sing Correctional Facility](https://www.expedia.ca/Sing-Sing-Correctional-Facility-Ossining.d553248621558038857.Vacation-Attraction). Whoever you're traveling with and whatever your budget, your dream Pleasantville vacation is only clicks away with Expedia. ## Top Pleasantville Vacation Deals Price found within the past 48 hours. Click for updated prices. ![Modern Comfort in the Heart of NYC](https://images.trvl-media.com/lodging/122000000/121820000/121816100/121816065/w1198h799x1y1-954a35fe_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Modern Comfort in the Heart of NYC Southeast Yonkers CA $1,051 per person Apr 29 - May 3 found 1 day ago Roundtrip flight included Toronto (YTO) to White Plains (HPN) 2/10 (1 review) ![Luxury 3BR Family Home Game Room Parking](https://images.trvl-media.com/lodging/125000000/124090000/124084400/124084363/2ea3fd3b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Luxury 3BR Family Home Game Room Parking Bryn Mawr CA $3,976 per person Jun 11 - Jun 15 found 24 hours ago Roundtrip flight included Toronto (YTO) to White Plains (HPN) 10/10 Exceptional! (1 review) Beautiful layout. Property had everything that was needed for an awesome stay. Reviewed on Feb 27, 2026 ![1 Hotel Brooklyn Bridge](https://images.trvl-media.com/lodging/16000000/15400000/15399700/15399642/b1e6b86c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### 1 Hotel Brooklyn Bridge CA $1,821 per person May 15 - May 17 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to Newark Liberty Intl. Airport (EWR) 8.8/10 Excellent! (1,000 reviews) Excellent staff, clean room, fantastic onsite restaurants. Reviewed on Mar 10, 2026 ![Arthouse Hotel New York City](https://images.trvl-media.com/lodging/1000000/20000/12200/12117/0e6cbb94_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Arthouse Hotel New York City Manhattan CA $1,662 per person Jun 8 - Jun 14 found 1 day ago Roundtrip non-stop flight included Hamilton (YHM) to Newark Liberty Intl. Airport (EWR) 8.8/10 Excellent! (1,843 reviews) Everything that I needed for my stay was met from the cleanliness and the staff that gave us a chauffeur ride to the airport. Not to mention the incredible coffee and bakery they have right in the hotel lobby! A true New York experience. Reviewed on Mar 24, 2026 ![The Ridge Hotel](https://images.trvl-media.com/lodging/2000000/1790000/1785000/1784927/28d93ae4_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Ridge Hotel Manhattan CA $1,367 per person Jun 8 - Jun 14 found 1 day ago Roundtrip non-stop flight included Hamilton (YHM) to Newark Liberty Intl. Airport (EWR) 8.2/10 Very Good! (1,032 reviews) Room small but clean. Staff were great, friendly and helpful. Reviewed on Mar 21, 2026 ## Ready to book your vacation to Pleasantville? Choose your dates ## Pleasantville Hotel Deals ![Baymont by Wyndham White Plains - Elmsford](https://images.trvl-media.com/lodging/1000000/10000/500/438/w8985h6000x10y0-9d556f34_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Baymont by Wyndham White Plains - Elmsford 540 Saw Mill River Rd Elmsford NY Fully refundableReserve now, pay when you stay CA $154 CA $176 total Apr 19 - Apr 20 includes taxes & fees 8.2/10 Very Good! (1,614 reviews) Everything amazing only the poolside hours is to 10pm the was closed before time and open again at 2pm we already have to leave at 12pm is not to much time for the pool next morning disappointing!! Reviewed on Mar 23, 2026 [](https://expedia.ca/Hotel-Search?startDate=19%2F04%2F2026&endDate=20%2F04%2F2026&selected=438&PinnedHotelID=438&HadPinnedHotel=true®ionId=9121) ![Homewood Suites by Hilton Teaneck Glenpointe](https://images.trvl-media.com/lodging/23000000/22520000/22514800/22514729/b257410e_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Homewood Suites by Hilton Teaneck Glenpointe 1 Glenwood Ave Ste A Teaneck NJ Fully refundableReserve now, pay when you stay CA $216 CA $247 total Mar 31 - Apr 1 includes taxes & fees 9.2/10 Wonderful! (1,739 reviews) Homewood Suites in Teaneck gave my relatives a very pleasant and comfortable stay during a special family occasion. I am a resident of Teaneck. I booked a 2-queen suite for my aunt, uncle, and cousin for 3 nights as part of a surprise 80th birthday celebration for my mother, and they truly enjoyed ... Reviewed on Mar 23, 2026 [](https://expedia.ca/Hotel-Search?startDate=31%2F03%2F2026&endDate=01%2F04%2F2026&selected=22514729&PinnedHotelID=22514729&HadPinnedHotel=true®ionId=9121) ![LIV Hotel Bronx - Newly Built](https://images.trvl-media.com/lodging/118000000/117970000/117967600/117967593/ef0e434d_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### LIV Hotel Bronx - Newly Built 3530 Webster Ave Bronx NY Fully refundableReserve now, pay when you stay CA $159 CA $188 total Mar 25 - Mar 26 includes taxes & fees 8.2/10 Very Good! (413 reviews) First of, the parking is very limited so do not expect that you'll be able to park inside. The person at the reception was not very friendly and it was hard to understand what he was saying. The room was barely clean, we found other people's hair all the time. There was no soap dispenser in the shower, ... Reviewed on Mar 23, 2026 [](https://expedia.ca/Hotel-Search?startDate=25%2F03%2F2026&endDate=26%2F03%2F2026&selected=117967593&PinnedHotelID=117967593&HadPinnedHotel=true®ionId=9121) [See all 1,456 properties in Pleasantville](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=25%2F03%2F2026&endDate=26%2F03%2F2026®ionId=9121) 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. ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations [](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations [](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Family Vacations [](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Vacations [](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Vacations [](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Vacations [](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Vacations [](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ### What to do in Pleasantville ![Helicopter landing in a field in New York](https://mediaim.expedia.com/localexpert/413462/e4624c52-b3f1-408c-bb02-0f208706f85a.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Introductory Helicopter Flight Lesson from Westchester CA $1,706 per traveller [](https://expedia.ca/things-to-do/introductory-helicopter-flight-lesson-from-westchester.a413462.activity-details) [See all activities in Pleasantville](https://expedia.ca/things-to-do/search?rid=9121) ## Explore a world of travel with Expedia \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app