Title: Port Chester Vacation Packages & Trips 2026 from CA $855 | Expedia.ca [Hotels in Port Chester](https://expedia.ca/Port-Chester-Hotels.d3000449448.Travel-Guide-Hotels)[Vacation Rentals in Port Chester](https://expedia.ca/Port-Chester-Vacation-Rentals.d3000449448.Travel-Guide-VacationRentals)[Flights to Port Chester](https://expedia.ca/Cheap-Flights-To-Port-Chester.d3000449448.Travel-Guide-Flights)[Port Chester Car Rentals](https://expedia.ca/Car-Rentals-In-Port-Chester.d3000449448.Car-Rental-Guide) ![](https://images.trvl-media.com/place/3000449448/6c414c92-13ff-43ae-8138-7454abbf0e50.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Port Chester 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 Port Chester Vacation When a city getaway is calling, answer it with a vacation package to Port Chester. The neighborhood of Downtown Stamford, which is good for history, bars and pubs and dining, makes a great base for your adventures. A trip to Port Chester is a wonderful opportunity to take in the sights. Check out well-known attractions like [Capitol Theatre](https://www.expedia.ca/Capitol-Theatre-Rye-Brook.d553248621532664534.Vacation-Attraction), [Doral Arrowwood Golf Club](https://www.expedia.ca/Doral-Arrowwood-Golf-Club-Rye-Brook.d553248621532664535.Vacation-Attraction) and [Clay Art Center Gallery](https://www.expedia.ca/Clay-Art-Center-Gallery-Rye-Brook.d553248621532664533.Vacation-Attraction). Stop daydreaming and start traveling. Browse the wide range of options on Expedia today and put your Port Chester vacation plans into gear! ## Top Port Chester Vacation Deals Price found within the past 48 hours. Click for updated prices. ![Hotel St. James](https://images.trvl-media.com/lodging/2000000/1150000/1144500/1144474/ecd19bcc_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel St. James Manhattan CA $855 per person Apr 2 - Apr 5 found 1 day ago Roundtrip flight included Toronto (YTO) to New York (JFK) 8.8/10 Excellent! (6,546 reviews) Clean room safe location Reviewed on Feb 8, 2026 ![Loews Regency New York Hotel](https://images.trvl-media.com/lodging/1000000/30000/25600/25559/c6e0103a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Loews Regency New York Hotel Manhattan CA $1,845 per person Apr 2 - Apr 7 found 1 day ago Roundtrip flight included Toronto (YTO) to New York (JFK) 9/10 Wonderful! (1,002 reviews) Staff were very accomodating and looked after my family well during our stay. Nothing was too difficult for them. Reviewed on Jan 17, 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 ![Arthouse Hotel New York City](https://images.trvl-media.com/lodging/1000000/20000/12200/12117/922bba74_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Arthouse Hotel New York City Manhattan CA $1,410 per person Mar 14 - Mar 21 found 1 day ago Roundtrip flight included Toronto (YTO) to New York (JFK) 8.8/10 Excellent! (1,678 reviews) Hip boutique hotel with an industrial cozy vibe. Rooms are sumple but have everything you need. The libby bar and cafe are nice. Attached to Serafina restaurant. Great lication overall and parking across the street. Reviewed on Feb 6, 2026 ## Ready to book your vacation to Port Chester? Choose your dates ## Port Chester 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 $171 CA $195 total Feb 22 - Feb 23 includes taxes & fees 8.2/10 Very Good! (1,526 reviews) Room was very clean and comfortable. Reviewed on Feb 1, 2026 [](https://expedia.ca/Hotel-Search?startDate=22%2F02%2F2026&endDate=23%2F02%2F2026&selected=438&PinnedHotelID=438&HadPinnedHotel=true®ionId=3000449448) ![Ly New York Hotel](https://images.trvl-media.com/lodging/102000000/101290000/101289700/101289650/00e8fce3_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Ly New York Hotel 15-61 127th St College Point NY Fully refundable CA $120 CA $143 total Feb 9 - Feb 10 includes taxes & fees 8.6/10 Excellent! (1,991 reviews) Clean room and good location by bus with transfer to Subway. Good City view. Parking was very difficult with too few on site spaces. Room was not made up when requested. No dresser or place to put clothes in room. Reviewed on Feb 5, 2026 [](https://expedia.ca/Hotel-Search?startDate=09%2F02%2F2026&endDate=10%2F02%2F2026&selected=101289650&PinnedHotelID=101289650&HadPinnedHotel=true®ionId=3000449448) ![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 $214 CA $291 total Mar 9 - Mar 10 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=09%2F03%2F2026&endDate=10%2F03%2F2026&selected=9979&PinnedHotelID=9979&HadPinnedHotel=true®ionId=3000449448) [See all 1,783 properties in Port Chester](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=09%2F02%2F2026&endDate=10%2F02%2F2026®ionId=3000449448) 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) ### Discover the most popular places to visit in Port Chester #### Blum Center for Health Though Blum Center for Health might be what brings you to town, perhaps you'll have a chance to explore more of Rye Brook while you are here. [](https://expedia.ca/Blum-Center-For-Health-Rye-Brook.d6207677.Vacation-Attraction) ### What to do in Port Chester ![LEGOLAND® Discovery Center Westchester Tickets](https://mediaim.expedia.com/localexpert/295953/21dd8cf6-029b-4741-9681-8cef3d435d35.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### LEGOLAND® Discovery Center Westchester Tickets CA $42 per adult **88%** of travellers recommend [](https://expedia.ca/things-to-do/legoland-discovery-center-westchester-tickets.a295953.activity-details) ![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 $914 per traveller [](https://expedia.ca/things-to-do/introductory-helicopter-flight-lesson-from-westchester.a413462.activity-details) [See all activities in Port Chester](https://expedia.ca/things-to-do/search?rid=3000449448) ## 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