Title: Port Chester Vacation Packages & Trips 2026 from CA $836 | 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 $836 per person Mar 12 - Mar 16 found 1 day ago Roundtrip non-stop flight included Hamilton (YHM) to New York (JFK) 8.8/10 Excellent! (6,546 reviews) The best place to stay on a budget if you’re planning to see Broadway shows. I’ve already reserved The St. James for my trip in April. Reviewed on Feb 6, 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 17 hours 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 17 hours 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 ![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 ![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 17 hours 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 ## 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 $166 CA $189 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 $119 CA $142 total Feb 10 - Feb 11 includes taxes & fees 8.6/10 Excellent! (1,968 reviews) They didn’t clean my room on time, I does have to call the front desk and ask for my room to be clean regardless putting on the sign for cleaning by the door Reviewed on Jan 29, 2026 [](https://expedia.ca/Hotel-Search?startDate=10%2F02%2F2026&endDate=11%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 $206 CA $281 total Feb 26 - Feb 27 includes taxes & fees 8.6/10 Excellent! (1,260 reviews) Very nice room, comfortable bed, spacious and clean. The staff was very friendly and helpful. The food was excellent. I would stay here again. Reviewed on Jan 30, 2026 [](https://expedia.ca/Hotel-Search?startDate=26%2F02%2F2026&endDate=27%2F02%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=08%2F02%2F2026&endDate=09%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 $1,729 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