Title: Old Greenwich Vacation Packages & Trips 2025/2026 from CA $521 | Expedia.ca [Old Greenwich Travel Guide](https://expedia.ca/Old-Greenwich.dx141226)[Hotels in Old Greenwich](https://expedia.ca/Old-Greenwich-Hotels.d141226.Travel-Guide-Hotels)[Vacation Rentals in Old Greenwich](https://expedia.ca/Old-Greenwich-Vacation-Rentals.d141226.Travel-Guide-VacationRentals)[Old Greenwich Car Rentals](https://expedia.ca/Car-Rentals-In-Old-Greenwich.d141226.Car-Rental-Guide) ![](https://images.trvl-media.com/place/8045/42990e16-67e7-4341-b4e9-29426d3b590a.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Old Greenwich Vacation Packages ## Book a Hotel + Flight or Car together to unlock savings Photo by Kate Persad - ## 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 Old Greenwich Vacation The stress-free way to experience this lively city is with a custom-made Old Greenwich vacation package. Stay in the neighborhood of Downtown Stamford, which is great for history, bars and pubs and dining or choose someplace else — our packages are all about you. If your trip to Old Greenwich includes a little sightseeing, hit up much-loved attractions like [Chelsea Piers](https://www.expedia.ca/Chelsea-Piers-Cove-East-Side-Shippan.d6247586.Vacation-Attraction), [Greenwich Avenue](https://www.expedia.ca/Greenwich-Avenue-Greenwich.d6207662.Vacation-Attraction) and [Stamford Town Center](https://www.expedia.ca/Stamford-Town-Center-Downtown-Stamford.d6125753.Vacation-Attraction). A few clicks is all it takes to put together the perfect Old Greenwich vacation on Expedia. ## Top Old Greenwich Vacation Deals Price found within the past 48 hours. Click for updated prices. ![Red Carpet Inn](https://images.trvl-media.com/lodging/3000000/2930000/2928100/2928037/49d204da_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Red Carpet Inn Cove - East Side - Shippan CA $521 per person Dec 24 - Dec 29 found 1 day ago Roundtrip flight included Detroit (DTW) to White Plains (HPN) 6.4/10 (1,018 reviews) Clean room. A/C heating unit worked to substitute for a missing blanket. Toilet paper, but no box of tissues. Reviewed on Oct 29, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-24/2025-12-29/?FromAirport=DTW&Destination=HPN&NumRoom=1&NumAdult=2&NumChild=0&hotelId=2928037&paandie=true&dealMarker=5SCtZfXSGJnbEuuNfbozKT9T1enzpdqS25aj19L0kIL6KAmqcNc8Bwy7foWa3_OH) ![Hampton Inn & Suites Yonkers](https://images.trvl-media.com/lodging/3000000/2650000/2647900/2647825/e36e4673_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hampton Inn & Suites Yonkers Northwest Yonkers CA $647 per person Dec 24 - Dec 29 found 1 day ago Roundtrip flight included Detroit (DTW) to White Plains (HPN) 8.2/10 Very Good! (1,583 reviews) Nice room, staff was very nice, would definitely recommend and great location- Reviewed on Nov 1, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-24/2025-12-29/?FromAirport=DTW&Destination=HPN&NumRoom=1&NumAdult=2&NumChild=0&hotelId=2647825&paandie=true&dealMarker=tDH_kYReY4XW45zcAWd32S5opoKPN30B6fHOEskSZ2EReiO23t63PZK4XqO5DI5h) ![Hotel NoMa, Trademark Collection by Wyndham](https://images.trvl-media.com/lodging/2000000/1090000/1088100/1088006/0bfe077b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel NoMa, Trademark Collection by Wyndham CA $833 per person Dec 20 - Dec 25 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to White Plains (HPN) 8/10 Very Good! (1,002 reviews) great night's sleep before surgery in Rye Reviewed on Nov 6, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-20/2025-12-25/?FromAirport=YTO&Destination=HPN&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1088006&paandie=true&dealMarker=bqrFqiSwaw3EXwqGqticxPsv9jZS9-vIk8PM7hS9qwD2LXXrdX2jvIheQ0Qaf8TJ) ![Luxury NY Home 3BR with Easy Parking ](https://images.trvl-media.com/lodging/104000000/103550000/103549600/103549522/772ee43d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Luxury NY Home 3BR with Easy Parking Southeast Yonkers CA $2,367 per person Dec 12 - Dec 15 found 16 hours ago Roundtrip flight included Toronto (YYZ) to White Plains (HPN) 3/10 (4 reviews) [](https://expedia.ca/go/package/search/FlightHotel/2025-12-12/2025-12-15/?FromAirport=YYZ&Destination=HPN&NumRoom=1&NumAdult=2&NumChild=0&hotelId=103549522&paandie=true&dealMarker=V0g0QMdJBZkQRfZcj4bxcdUPukAnmsSyofs37SH7tOSgmbA6RPcc1yeUUWXU3pqc) ![Global Luxury Suites White Plains](https://images.trvl-media.com/lodging/75000000/74130000/74125800/74125740/343ab6e5_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Global Luxury Suites White Plains CA $1,919 per person Dec 11 - Dec 18 found 1 day ago Roundtrip flight included Toronto (YTO) to White Plains (HPN) 6.8/10 (32 reviews) Being in an apartment building for an actual stay instead of a house was a first for myself and the family but overall a good stay. Reviewed on Sep 1, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-11/2025-12-18/?FromAirport=YTO&Destination=HPN&NumRoom=1&NumAdult=2&NumChild=0&hotelId=74125740&paandie=true&dealMarker=saTaPViTBPQvzLZUhCerYSFzrzAsTOdc4X3WKjm0AlYPsPJw7reNlekd6YdkIxxT) ## Ready to book your vacation to Old Greenwich? Choose your dates ## Old Greenwich Hotel Deals ![Hyatt Regency Greenwich](https://images.trvl-media.com/lodging/1000000/20000/18200/18180/19d28016_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hyatt Regency Greenwich 1800 E Putnam Avenue, Old Greenwich, CT Fully refundableReserve now, pay when you stay CA $251 CA $289 total Nov 23 - Nov 24 includes taxes & fees 8.2/10 Very Good! (1,014 reviews) Hotel is very pretty Reviewed on Nov 2, 2025 [](https://expedia.ca/Hotel-Search?startDate=23%2F11%2F2025&endDate=24%2F11%2F2025&selected=18180&PinnedHotelID=18180&HadPinnedHotel=true®ionId=141226) ![DoubleTree by Hilton Stamford](https://images.trvl-media.com/lodging/1000000/10000/5300/5292/f2f8be91_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### DoubleTree by Hilton Stamford 1 First Stamford Pl, Stamford, CT Fully refundableReserve now, pay when you stay CA $195 CA $225 total Nov 25 - Nov 26 includes taxes & fees 7.4/10 Good! (1,022 reviews) Nice people Reviewed on Nov 2, 2025 [](https://expedia.ca/Hotel-Search?startDate=25%2F11%2F2025&endDate=26%2F11%2F2025&selected=5292&PinnedHotelID=5292&HadPinnedHotel=true®ionId=141226) ![Royal Regency Hotel](https://images.trvl-media.com/lodging/1000000/50000/40900/40814/c5903df6_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Royal Regency Hotel 165 Tuckahoe Rd, Yonkers, NY Fully refundableReserve now, pay when you stay CA $146 CA $180 total Nov 23 - Nov 24 includes taxes & fees 8.2/10 Very Good! (2,353 reviews) Very nice and clean and staff is great Reviewed on Nov 2, 2025 [](https://expedia.ca/Hotel-Search?startDate=23%2F11%2F2025&endDate=24%2F11%2F2025&selected=40814&PinnedHotelID=40814&HadPinnedHotel=true®ionId=141226) [See all 1,385 properties in Old Greenwich](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=08%2F11%2F2025&endDate=09%2F11%2F2025®ionId=141226) 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) ## 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 ![QR code to download the app](data:image/png;base64,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)