Title: Port Chester Vacation Packages & Trips 2026 from CA $2,654 | 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. ![Beechmont - Perfect for Family Retreat!](https://images.trvl-media.com/lodging/120000000/119250000/119248500/119248411/6e17e1d7_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Beechmont - Perfect for Family Retreat! North End CA $2,654 per person Jun 8 - Jun 13 found 4 hours ago Roundtrip flight included Toronto (YTO) to New Haven (HVN) No reviews ![Modern Luxury Home w GameRoom & Parking](https://images.trvl-media.com/lodging/102000000/101330000/101326200/101326114/5bea3ddd_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Modern Luxury Home w GameRoom & Parking Southeast Yonkers CA $3,339 per person May 26 - May 31 found 1 day ago Roundtrip flight included Toronto (YTO) to White Plains (HPN) 7.2/10 Good! (5 reviews) This was an excellent House My birthday weekend was amazing I totally would book again Reviewed on Mar 17, 2024 ![The Fifth Avenue Hotel](https://images.trvl-media.com/lodging/97000000/96480000/96472700/96472655/183802ec_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Fifth Avenue Hotel Manhattan CA $3,802 per person Jun 7 - Jun 13 found 23 hours ago Roundtrip flight included Toronto (YTO) to Newark Liberty Intl. Airport (EWR) 9.6/10 Exceptional! (201 reviews) Absolutely everything. Amazingly appointed room, very friendly stafff. Reviewed on Mar 1, 2026 ![Casa Francesca 6BR Villa & Heated Pool](https://images.trvl-media.com/lodging/122000000/121730000/121727000/121726965/bbfe9075_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Casa Francesca 6BR Villa & Heated Pool CA $7,069 per person Jun 7 - Jun 14 found 4 hours ago Roundtrip flight included Toronto (YTZ) to Newark Liberty Intl. Airport (EWR) No reviews ![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 $5,111 per person Jun 7 - Jun 12 found 4 hours ago Roundtrip flight included Toronto (YTO) to Newark Liberty Intl. Airport (EWR) 8.8/10 Excellent! (1,000 reviews) Fantastic staycation! The spa was awesome and experience overall was solid. Would definitely stay here again! Reviewed on Mar 31, 2026 ## Ready to book your vacation to Port Chester? Choose your dates ## Port Chester Hotel Deals ![Four Points by Sheraton Flushing](https://images.trvl-media.com/lodging/69000000/68340000/68333500/68333401/5f479ffb_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Four Points by Sheraton Flushing 33-68 Farrington St Flushing NY Fully refundableReserve now, pay when you stay CA $198 CA $232 total Apr 12 - Apr 13 includes taxes & fees 9/10 Wonderful! (3,008 reviews) Very nice clean loved it Reviewed on Mar 31, 2026 [](https://expedia.ca/Hotel-Search?startDate=12%2F04%2F2026&endDate=13%2F04%2F2026&selected=68333401&PinnedHotelID=68333401&HadPinnedHotel=true®ionId=3000449448) ![Ly New York Hotel](https://images.trvl-media.com/lodging/102000000/101290000/101289700/101289650/9ebfee1f_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Ly New York Hotel 15-61 127th St College Point NY Fully refundableReserve now, pay when you stay CA $164 CA $193 total Apr 6 - Apr 7 includes taxes & fees 8.8/10 Excellent! (2,132 reviews) I’d say the Reviewed on Mar 30, 2026 [](https://expedia.ca/Hotel-Search?startDate=06%2F04%2F2026&endDate=07%2F04%2F2026&selected=101289650&PinnedHotelID=101289650&HadPinnedHotel=true®ionId=3000449448) ![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 $182 CA $208 total Apr 5 - Apr 6 includes taxes & fees 8.2/10 Very Good! (1,626 reviews) It wasn't that bad. I gave 4 stars because I found fake eyelashes in my bathroom. Plus the pool was warm but the pool area was super cold. Everyone was sitting with either a sweater or towel wrapped around them. Breakfast was great. Staff was pleasant. I would go back. Reviewed on Mar 29, 2026 [](https://expedia.ca/Hotel-Search?startDate=05%2F04%2F2026&endDate=06%2F04%2F2026&selected=438&PinnedHotelID=438&HadPinnedHotel=true®ionId=3000449448) [See all 1,811 properties in Port Chester](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=01%2F04%2F2026&endDate=02%2F04%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 ![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 $1,705 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