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.
Uscale 2BR Escape in the Heart of NYC
Bryn Mawr
CA $1,210
per person
Oct 1 - Oct 6
found 9 hours ago
Roundtrip flight included
Toronto (YYZ) to White Plains (HPN)
8/10 Very good! (1 review)
The house was very clean and the areas was quiet too. We had a nice spot to park the car. The staff was calling and checking on me if I didn’t have any issues with the check in. They were available all the time. The only thing we will need next time if possible is the washer and dryer and extra towels because we were 5 and only got 3 towels. But overall we enjoyed the stays.
Reviewed on Feb 21, 2026
Luxury NYC Home Game Room Free Parking
CA $1,324
per person
Oct 15 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to White Plains (HPN)
4/10 (1 review)
After flying in with four of us from Los Angeles on a Red Eye, we had to drive around for 4-5 hours until we were able to check in at 4pm, however after hours of trying to get into the property with no answer on the contact number ,we finally were able to have the local property manager come out and say that the property overbooked and had no room for us. I spent over 2 hours on the phone getting the run around by Expedia with mixed stories of our accommodations. FINALLY with now the story is that there was a plumbing problem and they would get us to another property from the original property manager and Expedia NOT doing a thing to help 4 of us stranded with no place to stay, we got to the other property. The new property was fine, but the most upsatting thing was dealing with Expedia trying to get a place for us to stay. Expedia tried saying they would cancel the accommodations and get us a Hotel but we would have to pay for the hotel and then wait for any credits or refund on our original booking. HIGHLY unacceptable by Expedia customer service. I am a GOLD member and spend quite a few thousand dollars a year for both business and pleasure and they did NOTHING to make me feel they were taking care of us. We basically lost a day of full work which cost my business over $1500 in non productive work.
Reviewed on May 4, 2026
Ready to book your vacation to Old Greenwich?
Old Greenwich Hotel Deals
Hyatt Regency Greenwich
1800 E Putnam Avenue Old Greenwich CT
Fully refundableReserve now, pay when you stay
CA $248
CA $285 total
Sep 6 - Sep 7
includes taxes & fees
Tarrytown House Estate
49 E Sunnyside Lane Tarrytown NY
Fully refundableReserve now, pay when you stay
CA $221
CA $288 total
Aug 23 - Aug 24
includes taxes & fees
8.2/10 Very good! (1,244 reviews)
"The grounds are absolutely beautiful with lots to do. Unfortunately we were only in for a quick overnight so we couldn’t enjoy anything but I would go back again!"
Reviewed on Aug 14, 2026
Royal Regency Hotel
165 Tuckahoe Rd Yonkers NY
Fully refundableReserve now, pay when you stay
CA $152
CA $186 total
Aug 30 - Aug 31
includes taxes & fees
8.6/10 Excellent! (2,816 reviews)
"3rd Floor usually has a bad sewer smell ..."
Reviewed on Aug 13, 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 $940 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.
