Old Greenwich Vacation Packages
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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, Greenwich Avenue and Stamford Town Center. 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.
Tarrytown House Estate
CA $899
per person
Oct 16 - Oct 19
found 3 hours ago
Roundtrip flight included
Toronto (YTO) to White Plains (HPN)
8.2/10 Very good! (1,272 reviews)
This place could be spectacular, but our experience was anything but that. The grounds and property are gorgeous but our room was depressing and in desperate need of renovation. The bathroom was in such bad shape that we didn’t even want to use it - a badly chipped and stained toilet and mold and dirt covering the tile and caulking in the bath/shower. The room was bare bones with a phone that didn’t work and not enough towels. The beds were ok. There was no elevator to our lower level room, which meant having to lug our heavy bags up and down. The outside of this place does not match the inside. We were very disappointed and would not stay again unless the rooms undergo a major renovation.
Reviewed on Sep 16, 2026
Modern Luxury Home w GameRoom & Parking
Southeast Yonkers
CA $3,066
per person
Oct 22 - Oct 25
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to White Plains (HPN)
4.6/10 (11 reviews)
Though the privous occupants refused to vacate the property in time but the landlord was suupportive went out of their way and provided a refund option and an alternative...we took the alternative which happen to be better than the originally booked property ...
Will use this management and property owner in our upcoming short terms rentals.....
Reviewed on Sep 13, 2026
Modern Comfort in the Heart of NYC
Southeast Yonkers
CA $1,006
per person
Oct 22 - Oct 25
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to White Plains (HPN)
3.6/10 (4 reviews)
It took calling the booking website customer service to get in contact with the host. I end up getting a different property that the one I reserved but the new on was more bedrooms, at the end I work out but it took some long coy with the host.
Reviewed on Jun 29, 2026
Delamar Greenwich Harbor
CA $1,663
per person
Nov 30 - Dec 4
found 1 day ago
Roundtrip flight included
Toronto (YTO) to White Plains (HPN)
9.4/10 Exceptional! (1,002 reviews)
The property was strikingly beautiful, well maintained, very efficient and pleasant staff and the restaurant L’scala was well run and excellent presentation and food quality
Reviewed on Sep 14, 2026
Ready to book your vacation to Old Greenwich?
Old Greenwich Hotel Deals
Hyatt Regency Greenwich
1800 E Putnam Avenue Old Greenwich CT
CA $306
CA $352 total
Oct 4 - Oct 5
includes taxes & fees
Tarrytown House Estate
49 E Sunnyside Lane Tarrytown NY
CA $208
CA $288 total
Oct 1 - Oct 2
includes taxes & fees
8.2/10 Very good! (1,305 reviews)
"This place could be spectacular, but our experience was anything but that. The grounds and property are gorgeous but our room was depressing and in desperate need of renovation. The bathroom was in such bad shape that we didn’t even want to use it - a badly chipped and stained toilet and mold and ..."
Reviewed on Sep 16, 2026
Royal Regency Hotel
165 Tuckahoe Rd Yonkers NY
CA $167
CA $204 total
Sep 27 - Sep 28
includes taxes & fees
8.6/10 Excellent! (2,854 reviews)
"The sound roofing of the hotel windows was extremely poor, almost nonexistent. Since the hotel is located next to a highway, the noise from the traffic went on all night, and it felt as if I were sleeping directly beside the road. The noise was not isolated at all. The breakfast was comparable to ..."
Reviewed on Sep 16, 2026
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.
Stay near popular Old Greenwich attractions
Greenwich Point Park
9.2/10 (23 reviews)
After visiting Greenwich Point Park, make a plan to see the other sights and activities in Old Greenwich. While in this family-friendly area, you can savor the top-notch restaurants.
Frequently asked questions
How much does an Old Greenwich vacation package cost?
You'll find cheap prices from CA $899 on Expedia for your Old Greenwich getaway. However, factors like the length of stay, the season and your choice of hotel will determine how much your vacation to Old Greenwich costs.
What are the cheapest months to go to Old Greenwich?
January, February and August are great times to search for cheap Old Greenwich vacation packages. Opting to travel in less busy months means you can generally find reduced prices on flights and hotels.
How many days is enough for Old Greenwich?
Old Greenwich vacations can be short or long, but to get a real feel for this place, we'd say 2 days is a good ballpark. In this timeframe, you can fit in headline attractions like Greenwich Point Park and Bruce Museum of Arts and Science as well as hidden gems. Don't skip cool areas such as Downtown Stamford and Cove - East Side - Shippan either. If you plan wisely, you may even be able to take a day trip from Old Greenwich too.
How to find the best Old Greenwich package deals?
Use Expedia's handy filters to help you find some fabulous Old Greenwich package deals. When you start your search, just set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your adventure for midweek, or browse for Old Greenwich package deals in the off-season. Play around with your travel dates and you may land even better discounts. As a rule of thumb, it's usually best to book your vacation package well in advance.
Is it cheaper to book an Old Greenwich vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your car rental, hotel and flight into one great-value price and you could save hundreds of dollars. You'll typically get a better deal than booking each component individually. And you'll still enjoy the freedom to create a customized Old Greenwich vacation by choosing your preferred accommodation type, airline and car class.
When to book a vacation package to Old Greenwich?
If you have your Old Greenwich travel dates finalized, book early to bag some fantastic deals. With Expedia, you can generally reserve some flights up to one year ahead of time. Prefer spur-of-the-moment adventures? Our last-minute deals are great for jetting off on a whim.
How to plan a trip to Old Greenwich?
- Choose the right time to travel: Your schedule, preferred season and the type of weather you like can all influence your decision on when to travel to Old Greenwich.
- Set a budget: Factor in expenses such as transportation, flights and meals when calculating how much to put aside for your trip to Old Greenwich. Then, pick a property that suits your budget, whether that's a wallet-friendly option or a more upscale retreat.
- Work out your trip length: Consider how much time you'd like to spend discovering Old Greenwich. Plan your days so you can get to all the attractions and activities you're interested in without rushing.
- Bundle your accommodations and airfare: After you've nailed down your dates and duration, book the right Old Greenwich vacation package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
