Title: Old Greenwich Vacation Packages & Trips 2025/2026 from CA $873 | Expedia.ca

  

[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)

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# Old Greenwich Vacation Packages

## Book a Hotel + Flight or Car together to unlock savings

-   ## 
    
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Save up to CA $1,096 when you book a flight and hotel together\*

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With over 300,000 hotels worldwide, it's easy to create a perfect package

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#### 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.

![The Armon Stamford Hotel & Conference](https://images.trvl-media.com/lodging/90000000/89820000/89818900/89818854/99ae042b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Armon Stamford Hotel & Conference

Ridgeway-Bullshead

CA $873

per person

Nov 2 - Nov 7

found 4 hours ago

Roundtrip flight included

Calgary (YYC) to White Plains (HPN)

7.8/10 Good! (520 reviews)

Our room, Junior Room, 2 Double Beds, was very spacious and newly renovated. It was very clean and quiet. We had very friendly, responsive and helpful service. Our only disappointment was to find the whirlpool was closed.

Reviewed on Sep 18, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2025-11-02/2025-11-07/?FromAirport=YYC&Destination=HPN&NumRoom=1&NumAdult=2&NumChild=0&hotelId=89818854&paandie=true&dealMarker=23pNa6ItKdCZPQ581K2fho4JR4YFSo07rSB5lPXXHcosqb0xajc73qOBLYIX17rO)

![2 Cabins w/ Hot Tub, Pool, Firepit, & Outdoor Dining Minutes From Wineries](https://images.trvl-media.com/lodging/116000000/115920000/115916800/115916706/fad07f14_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### 2 Cabins w/ Hot Tub, Pool, Firepit, & Outdoor Dining Minutes From Wineries

CA $3,106

per person

Nov 6 - Nov 12

found 12 hours ago

Roundtrip flight included

Toronto (YYZ) to White Plains (HPN)

No reviews

[](https://expedia.ca/go/package/search/FlightHotel/2025-11-06/2025-11-12/?FromAirport=YYZ&Destination=HPN&NumRoom=1&NumAdult=2&NumChild=0&hotelId=115916706&paandie=true&dealMarker=jHT3N1Ek5bIKLpyRMc9UkcIxNMCISfwB7h_fvCzSnnZCsJroHcmsR014jGvVGesQ)

![Hampton Inn & Suites Poughkeepsie](https://images.trvl-media.com/lodging/2000000/1930000/1927100/1927088/47fa2e85_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hampton Inn & Suites Poughkeepsie

Crown Heights

CA $918

per person

Nov 6 - Nov 12

found 12 hours ago

Roundtrip flight included

Toronto (YYZ) to White Plains (HPN)

8.6/10 Excellent! (1,000 reviews)

This is an old Hampton Inn that has been renovated, but it’s very sterile and “Vanilla”! There isn’t one picture in the room so it has an institutional feel. The bed faces the window but the TV is on a side wall so I had to crank my head sideways to see it. These Hampton Inns can be a mixed bag. No apples or cookies here. The fitness room didn’t have water. The help is very nice. Breakfast fine, but the rooms are just boring. They do have a great laundry room with new machines. I would reconfigure the rooms. I used to be in the design business so maybe I’m a bit harsh.

Reviewed on Sep 17, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2025-11-06/2025-11-12/?FromAirport=YYZ&Destination=HPN&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1927088&paandie=true&dealMarker=jHT3N1Ek5bIKLpyRMc9UkcXp6nd8kpEuy9fsBoWEHU5e_X-wA-m1iMp0Wi4-gsxg)

![Luxury Apartments by Hyatus at The Asher](https://images.trvl-media.com/lodging/106000000/105900000/105898500/105898494/1e9f19ec_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Luxury Apartments by Hyatus at The Asher

Downtown Stamford

CA $1,320

per person

Nov 6 - Nov 11

found 5 hours ago

Roundtrip non-stop flight included

Vancouver (YVR) to White Plains (HPN)

10/10 Exceptional! (17 reviews)

cleanliness. quiet.

Reviewed on Aug 20, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2025-11-06/2025-11-11/?FromAirport=YVR&Destination=HPN&NumRoom=1&NumAdult=2&NumChild=0&hotelId=105898494&paandie=true&dealMarker=_TFYsbjc4pUjnKFqrp1Y4i5b-9oC6f0QNo_DBGYLK-yIiJGeRZuPRn9vplV_5r-a)

![Charcoal Chalet by Avantstay A+ Design w/ Firepit](https://images.trvl-media.com/lodging/105000000/104830000/104822600/104822555/cb1656ee_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Charcoal Chalet by Avantstay A+ Design w/ Firepit

CA $1,400

per person

Nov 6 - Nov 12

found 12 hours ago

Roundtrip flight included

Toronto (YYZ) to White Plains (HPN)

No reviews

[](https://expedia.ca/go/package/search/FlightHotel/2025-11-06/2025-11-12/?FromAirport=YYZ&Destination=HPN&NumRoom=1&NumAdult=2&NumChild=0&hotelId=104822555&paandie=true&dealMarker=jHT3N1Ek5bIKLpyRMc9UkWwFmZuhaKnZMrJRPilW9P16dqYhzfILRUHUw8rHgf3k)

## 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)

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Hyatt Regency Greenwich

1800 E Putnam Avenue, Old Greenwich, CT

Fully refundableReserve now, pay when you stay

CA $280

CA $322 total

Oct 2 - Oct 3

includes taxes & fees

8.2/10 Very Good! (1,006 reviews)

"The staff are beautiful and top notch!! They made me and my daughters feel like we had a home away from home.They were consistently kind and accommodating. We want to send a special thank you to the night manager Sean (I know that's not your whole name). Even when he was busy he took the time to ..."

Reviewed on Sep 15, 2025

[](https://expedia.ca/Hotel-Search?startDate=02%2F10%2F2025&endDate=03%2F10%2F2025&selected=18180&PinnedHotelID=18180&HadPinnedHotel=true&regionId=141226)

![Hampton Inn White Plains/Tarrytown](https://images.trvl-media.com/lodging/1000000/30000/23300/23291/d5b0e16e_y.jpg?impolicy=resizecrop&rw=340&ch=150)

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Hampton Inn White Plains/Tarrytown

200 West Main Street, Elmsford, NY

Fully refundableReserve now, pay when you stay

CA $182

CA $208 total

Sep 28 - Sep 29

includes taxes & fees

7.8/10 Good! (1,177 reviews)

Kathleen from Coventry

"We were early but they made accommodations for us until our room was ready. We enjoyed our breakfast and the clean towels we picked up every morning as we were there for business so would not be needing the housekeeping. Very agreeable staff."

Reviewed on Sep 15, 2025

[](https://expedia.ca/Hotel-Search?startDate=28%2F09%2F2025&endDate=29%2F09%2F2025&selected=23291&PinnedHotelID=23291&HadPinnedHotel=true&regionId=141226)

![Royal Regency Hotel](https://images.trvl-media.com/lodging/1000000/50000/40900/40814/c5903df6_y.jpg?impolicy=resizecrop&rw=340&ch=150)

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Royal Regency Hotel

165 Tuckahoe Rd, Yonkers, NY

Fully refundableReserve now, pay when you stay

CA $152

CA $186 total

Sep 21 - Sep 22

includes taxes & fees

8.2/10 Very Good! (2,267 reviews)

Lovely stay

"Beautiful lobby, nice room with a neat sliding bathroom wall feature, and I appreciated that there was a fridge in the room and microwave available."

Reviewed on Sep 15, 2025

[](https://expedia.ca/Hotel-Search?startDate=21%2F09%2F2025&endDate=22%2F09%2F2025&selected=40814&PinnedHotelID=40814&HadPinnedHotel=true&regionId=141226)

[See all 1,322 properties in Old Greenwich](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=20%2F09%2F2025&endDate=21%2F09%2F2025&regionId=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)

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\* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.

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![QR code to download the app](data:image/png;base64,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)