Title: Port Chester Vacation Packages 2026 from $396 | Expedia.com [Port Chester Travel Guide](https://expedia.com/Port-Chester.dx3000449448)[Hotels in Port Chester](https://expedia.com/Port-Chester-Hotels.d3000449448.Travel-Guide-Hotels)[Vacation Rentals in Port Chester](https://expedia.com/Port-Chester-Vacation-Rentals.d3000449448.Travel-Guide-VacationRentals)[Flights to Port Chester](https://expedia.com/Cheap-Flights-To-Port-Chester.d3000449448.Travel-Guide-Flights)[Car Rentals in Port Chester](https://expedia.com/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 Vacations from $396 ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to $1,045 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.com/Capitol-Theatre-Rye-Brook.d553248621532664534.Vacation-Attraction), [Doral Arrowwood Golf Club](https://www.expedia.com/Doral-Arrowwood-Golf-Club-Rye-Brook.d553248621532664535.Vacation-Attraction) and [Clay Art Center Gallery](https://www.expedia.com/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! ## The Latest Port Chester vacation packages Price found within the past 48 hours. Click for updated prices. ![Sheraton New York Times Square Hotel](https://images.trvl-media.com/lodging/1000000/10000/100/87/576ccb20_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Sheraton New York Times Square Hotel Manhattan Save 100% on your flight $396 per person May 7 - May 11 found 1 day ago Roundtrip flight included Atlanta (ATL) to Newark Liberty Intl. Airport (EWR) 7.4/10 Good! (5,413 reviews) Rooms ok bed small / crazy up charges for everything Reviewed on Feb 28, 2026 ![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 $595 per person May 7 - May 11 found 1 day ago Roundtrip flight included Atlanta (ATL) to Newark Liberty Intl. Airport (EWR) 8.8/10 Excellent! (6,546 reviews) The room was okay , in a great place in terms of walking distance to time square, broadway, Reviewed on Feb 28, 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 $1,550 per person May 12 - May 17 found 1 day ago Roundtrip flight included Atlanta (ATL) to Newark Liberty Intl. Airport (EWR) 9/10 Wonderful! (1,002 reviews) Excellent stay, very clean spacious rooms. Location is great - close to everything. Only downfall was the bathroom, very tiny with a pedestal sink right next to the toilet, not great for women who need to get ready. Reviewed on Feb 24, 2026 ![JW Marriott Essex House New York](https://images.trvl-media.com/lodging/1000000/540000/534200/534143/04695212_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### JW Marriott Essex House New York Manhattan Save 100% on your flight $1,103 per person Apr 7 - Apr 11 found 1 day ago Roundtrip flight included Atlanta (ATL) to Newark Liberty Intl. Airport (EWR) 8.8/10 Excellent! (1,001 reviews) Great location - expensive for your return. Reviewed on Feb 16, 2026 Don't see what you're looking for? See all available trips from Columbus to Port Chester [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-03-28/2026-04-04/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=LGA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.com/deals?rfrr=PKG_SPRING_PROMO_3000449448) ### Discover the most popular places to visit in Port Chester ![Duran Duran plays the Capitol Theatre in Port Chester, NY in support of their Paper Gods album. Here they perform "Rio" to close out the night. #duranlive](https://images.trvl-media.com/place/3000449448/2d599a75-d90c-4c10-9598-382ebb82f3c5.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Capitol Theatre Enjoy a show at Capitol Theatre, a theater with a story to tell in Port Chester. Discover the entertainment choices and shops in this family-friendly area. [](https://expedia.com/Capitol-Theatre-Rye-Brook.d553248621532664534.Vacation-Attraction) #### Doral Arrowwood Golf Club Enjoy a round of golf in Rye Brook at Doral Arrowwood Golf Club. Check out the shops and top-notch restaurants in this family-friendly area. [](https://expedia.com/Doral-Arrowwood-Golf-Club-Rye-Brook.d553248621532664535.Vacation-Attraction) #### 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.com/Blum-Center-For-Health-Rye-Brook.d6207677.Vacation-Attraction) ### What to do in Port Chester ![Self Guided Audio Ghost Tour of Sleepy Hollow](https://mediaim.expedia.com/localexpert/50948961/ff504dad-c9c4-4ba4-b5dd-5dc27084bb16.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Self Guided Audio Ghost Tour of Sleepy Hollow $10 per adult [](https://expedia.com/things-to-do/self-guided-audio-ghost-tour-of-sleepy-hollow.a50948961.activity-details) ![Guided Kayak Fishing Tour](https://mediaim.expedia.com/localexpert/2102424/43814a51-0bb4-48f1-8df8-7d91cb93eda2.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Guided Kayak Fishing Tour $564 per adult [](https://expedia.com/things-to-do/guided-kayak-fishing-tour.a2102424.activity-details) [See all activities in Port Chester](https://expedia.com/things-to-do/search?rid=3000449448) ## Port Chester Hotel Deals ![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 $78 nightly $93 total Mar 1 - Mar 2 Total with taxes and fees 8.8/10 Excellent! (2,039 reviews) Was good Reviewed on Feb 28, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F1%2F2026&endDate=3%2F2%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 $128 nightly $146 total Mar 1 - Mar 2 Total with taxes and fees 8.2/10 Very Good! (1,577 reviews) Very noisy this time. I normally enjoy it there. Teens and young kids all down the hallway running and making noise all night until early morning. This made my stay very uncomfortable. Reviewed on Feb 24, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F1%2F2026&endDate=3%2F2%2F2026&selected=438&PinnedHotelID=438&HadPinnedHotel=true®ionId=3000449448) ![Highbridge Hotel](https://images.trvl-media.com/lodging/93000000/92430000/92420700/92420628/d6a409cb_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Highbridge Hotel 1263 Edward L Grant Highway Bronx NY Fully refundableReserve now, pay when you stay $70 nightly $84 total Mar 16 - Mar 17 Total with taxes and fees 9.2/10 Wonderful! (4,027 reviews) Poor management. The front desk is not professional. Reviewed on Feb 28, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F16%2F2026&endDate=3%2F17%2F2026&selected=92420628&PinnedHotelID=92420628&HadPinnedHotel=true®ionId=3000449448) [See all 1,800 properties in Port Chester](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=3%2F1%2F2026&endDate=3%2F2%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. ## Find the Best Port Chester Vacation Packages ## Port Chester Essential Information | Language | English | | --------------- | ------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------- | | Currency | U.S dollars | | Closest Airport | John F. Kennedy Intl. Airport (JFK) | | Population | 29,600 | | Top Sights | [Capitol Theatre](https://www.expedia.com/Capitol-Theatre-Rye-Brook.d553248621532664534.Vacation-Attraction), [Doral Arrowwood Golf Club](https://www.expedia.com/Doral-Arrowwood-Golf-Club-Rye-Brook.d553248621532664535.Vacation-Attraction) and [Clay Art Center Gallery](https://www.expedia.com/Clay-Art-Center-Gallery-Rye-Brook.d553248621532664533.Vacation-Attraction) | ## More vacations you might like ![](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.com/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.com/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) 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Month](https://forever.travel-assets.com/flex/flexmanager/images/2023/05/10/mesog-34434-card-venice.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Where to go when [](https://expedia.com/lp/b/where-to-go-when?rfrr=editorial.Where_to%20go%20when.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/21/honeymoon_hawaii.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Honeymoon Vacations [](https://expedia.com/lp/theme-vacations/honeymoon-vacations?rfrr=editorial.Honeymoon_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/Mountain-vacations.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Mountain Vacations [](https://expedia.com/lp/theme-vacations/mountain-vacations?rfrr=editorial.Mountain_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/fishing-vacations-2.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Fishing Vacations [](https://expedia.com/lp/theme-vacations/fishing-vacations?rfrr=editorial.Fishing_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2019/05/16/Hyatt%20Zilara%20Cancun%20-%20All%20Inclusive%20-%20Adults%20Only.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Adults Only Vacations [](https://expedia.com/lp/theme-vacations/adults-only-vacations?rfrr=editorial.Adults_Only%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/waterpark-vacations.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Waterpark Vacations [](https://expedia.com/lp/theme-vacations/waterpark-vacations?rfrr=editorial.Waterpark_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/08/Caribean_scuba_diving.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Scuba Diving Vacations [](https://expedia.com/lp/theme-vacations/scuba-diving-vacations?rfrr=editorial.Scuba_Diving%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/08/aruba_yoga.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Yoga Vacations [](https://expedia.com/lp/theme-vacations/yoga-vacations?rfrr=editorial.Yoga_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2023/04/04/EPS-RBC-SummerBeachVacations-AdobeStock_206356322.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Cheap Vacations [](https://expedia.com/lp/theme-vacations/cheap-vacations?rfrr=editorial.Cheap_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/06/26/1175883311.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Solo Vacations [](https://expedia.com/lp/b/vacations/solo-vacations?rfrr=editorial.Solo_Vacations.click) ## Frequently asked questions ### How much does a Port Chester vacation package cost? ### What are the cheapest months to go to Port Chester? ### How many days is enough for Port Chester? ### Is it worth booking a vacation package to Port Chester? ### How to find the best Port Chester package deals? ### Is it cheaper to book a Port Chester vacation as a package? ### When to book a vacation package to Port Chester? ### Does Expedia offer Book Now, Pay Later Port Chester vacation packages? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - More ways to book - [New York Hotels ](https://www.expedia.com/New-York-Hotels.d178293.Travel-Guide-Hotels) - [Hotels near Capitol Theatre ](https://www.expedia.com/Capitol-Theatre-Hotels.0-l553248621532664534-0.Travel-Guide-Filter-Hotels) - [Hotels near Blum Center for Health ](https://www.expedia.com/Blum-Center-For-Health-Hotels.0-l6207677-0.Travel-Guide-Filter-Hotels) - [Rye Brook Hotels ](https://www.expedia.com/Rye-Brook-Hotels.d10820.Travel-Guide-Hotels) - [Resorts & Hotels with Spas in Rye Brook ](https://www.expedia.com/Rye-Brook-Hotels-Spa-Hotel.0-0-d10820-tSpaHotel.Travel-Guide-Filter-Hotels) - [Apartments in Rye Brook 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