Title: Pleasantville Vacation Packages & Trips 2026 from CA $1,469 | 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. ![1 Hotel Brooklyn Bridge](https://images.trvl-media.com/lodging/16000000/15400000/15399700/15399642/7801a5d8_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### 1 Hotel Brooklyn Bridge CA $1,469 per person Apr 25 - Apr 27 found 1 day ago Roundtrip flight included Toronto (YTO) to New York (JFK) 8.8/10 Excellent! (1,000 reviews) The entire stay was exceptional! From the point of entry to departure 10/10 Reviewed on Jan 29, 2026 ![1 Hotel Central Park](https://images.trvl-media.com/lodging/10000000/9220000/9215600/9215515/524d3c3f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### 1 Hotel Central Park Manhattan CA $2,010 per person Apr 25 - Apr 29 found 1 day ago Roundtrip flight included Toronto (YTO) to New York (JFK) 9/10 Wonderful! (1,001 reviews) Excellent stay! Friendly staff, comfortable, beautiful rooms & lobby. Reviewed on Feb 2, 2026 ![The Fifth Avenue Hotel](https://images.trvl-media.com/lodging/97000000/96480000/96472700/96472655/d0a5c1e1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Fifth Avenue Hotel Manhattan CA $2,194 per person Apr 25 - Apr 29 found 1 day ago Roundtrip flight included Toronto (YTO) to Newark Liberty Intl. Airport (EWR) 9.6/10 Exceptional! (159 reviews) Staff were lovely, helpful and pleasant. Turndown service way too late, though—9:45 might catch some guests sleeping. Reviewed on Jan 3, 2026 ![The Pierre, A Taj Hotel, New York](https://images.trvl-media.com/lodging/1000000/30000/20300/20213/8b7fc5c6_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Pierre, A Taj Hotel, New York Manhattan CA $1,883 per person Apr 25 - Apr 29 found 1 day ago Roundtrip flight included Toronto (YTO) to Newark Liberty Intl. Airport (EWR) 9.2/10 Wonderful! (1,007 reviews) Staff warm, & welcoming, bar, great breakfast, & restaurant lovely, don’t miss coffee at the bar in the morning & Friday with the Martinis piano singers. Reviewed on Feb 5, 2026 ![The Towers at Lotte New York Palace](https://images.trvl-media.com/lodging/5000000/4200000/4195300/4195208/02d4f5a0_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Towers at Lotte New York Palace Manhattan CA $2,093 per person Apr 25 - Apr 29 found 21 hours ago Roundtrip flight included Toronto (YTO) to New York (JFK) 9.2/10 Wonderful! (638 reviews) Close to major shopping and multiple dining options Reviewed on Jan 21, 2026 ## Ready to book your vacation to Pleasantville? Choose your dates ## Pleasantville Hotel Deals ![Sonesta White Plains Downtown](https://images.trvl-media.com/lodging/1000000/10000/10000/9979/2c718cc1_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Sonesta White Plains Downtown 66 Hale Ave White Plains NY Fully refundableReserve now, pay when you stay CA $216 CA $292 total Mar 1 - Mar 2 includes taxes & fees 8.6/10 Excellent! (1,273 reviews) Staff were courteous and helpful. Great location! Reviewed on Feb 3, 2026 [](https://expedia.ca/Hotel-Search?startDate=01%2F03%2F2026&endDate=02%2F03%2F2026&selected=9979&PinnedHotelID=9979&HadPinnedHotel=true®ionId=9121) ![Homewood Suites by Hilton Teaneck Glenpointe](https://images.trvl-media.com/lodging/23000000/22520000/22514800/22514729/de45f1a7_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 $201 CA $230 total Feb 19 - Feb 20 includes taxes & fees 9/10 Wonderful! (1,714 reviews) Staff and parking Reviewed on Feb 5, 2026 [](https://expedia.ca/Hotel-Search?startDate=19%2F02%2F2026&endDate=20%2F02%2F2026&selected=22514729&PinnedHotelID=22514729&HadPinnedHotel=true®ionId=9121) ![EVEN Hotel Norwalk by IHG](https://images.trvl-media.com/lodging/1000000/10000/2600/2584/4cb7d7eb_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### EVEN Hotel Norwalk by IHG 426 Main Ave, Route 7 Norwalk CT Fully refundable CA $178 CA $204 total Feb 12 - Feb 13 includes taxes & fees 8.2/10 Very Good! (1,072 reviews) Staff was very kind and accommodating. Premises are clean and welcoming. Very nice stay. Reviewed on Jan 27, 2026 [](https://expedia.ca/Hotel-Search?startDate=12%2F02%2F2026&endDate=13%2F02%2F2026&selected=2584&PinnedHotelID=2584&HadPinnedHotel=true®ionId=9121) [See all 1,438 properties in Pleasantville](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=08%2F02%2F2026&endDate=09%2F02%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 $1,729 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