Old Greenwich Holidays from £968

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    Packages with flights are ATOL protected

Your Old Greenwich Holiday

The stress-free way to experience this lively city is with a custom-made Old Greenwich holiday package. Stay in the neighbourhood 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 Centre. A few clicks is all it takes to put together the perfect Old Greenwich holiday on Expedia.

Top Old Greenwich Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Tarrytown House Estate

Tarrytown House Estate

3.5 out of 5
Price was £1,283, price is now £968 per person
£968
per person
23 Sept - 28 Sept
found 7 hours ago
Return flight included
Manchester (MAN) to White Plains (HPN)
8.2/10 Very good! (1,131 reviews)
Unique property a bit older!

Reviewed on 7 Jul 2026

Luxury NY Home with Free Parking

Luxury NY Home with Free Parking

4 out of 5
Save 100% on your flight
Price was £3,341, price is now £2,191 per person
£2,191
per person
23 Sept - 28 Sept
found 7 hours ago
Return flight included
Manchester (MAN) to White Plains (HPN)
8/10 Very good! (1 review)
Rooms were very clean, well decorated however bathrooms were not. Parking was accessible and perfect. Some appliances did not work like iron stained my clothes and coffee machine did not work. Everything else was fine.

Reviewed on 8 Nov 2025

3BR Prime Luxury NY - Free Parking

3BR Prime Luxury NY - Free Parking

2 out of 5
Save 100% on your flight
Price was £2,736, price is now £1,846 per person
£1,846
per person
23 Sept - 28 Sept
found 7 hours ago
Return flight included
Manchester (MAN) to White Plains (HPN)
6/10 (1 review)
Check-in was confusing and poorly organized, which made the start of the stay frustrating. The room itself was fine and comfortable, but the photos on the website were misleading and didn’t match what we saw in person. Overall, an okay room but not the experience we expected.

Reviewed on 30 Mar 2026

Luxury NYC Home Game Room Free Parking

Luxury NYC Home Game Room Free Parking

4 out of 5
Price was £1,832, price is now £1,328 per person
£1,328
per person
23 Sept - 28 Sept
found 7 hours ago
Return flight included
Manchester (MAN) 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 4 May 2026

Luxury NYC Home with Free Parking for 12

Luxury NYC Home with Free Parking for 12

4 out of 5
Price was £1,429, price is now £1,071 per person
£1,071
per person
12 Sept - 17 Sept
found 11 hours ago
Return direct flight included
London (LGW) to White Plains (HPN)
2/10 (1 review)
Place didn't exist. Host did not respond to requests to clarify check-in. Upon arriving, the location was not as described and an individual who answered the door informed our party this was not a rental property. Had to last minute book elsewhere.

Reviewed on 11 Feb 2026

Old Greenwich Essential Information

Language
English
Currency
U.S dollars
Closest Airport
John F. Kennedy Intl. Airport (JFK)
Population
6,600
Max Temp Winter
2ºC
Max Temp Summer
27ºC
Top Sights
Norwalk Maritime Aquarium, Compo Beach and The Maritime Aquarium

Top hotels in Old Greenwich

Hyatt Regency Greenwich

Hyatt Regency Greenwich

4 out of 5
1800 E Putnam Avenue Old Greenwich CT
Fully refundableReserve now, pay when you stay
The price is £164 per night from 26 Jul to 27 Jul
£164
26 Jul - 27 Jul
includes taxes & fees
8.6/10 Excellent! (1,065 reviews)
"Loved the resort feel."

Reviewed on 6 Jul 2026

Hyatt Regency Greenwich
Hampton Inn White Plains/Tarrytown

Hampton Inn White Plains/Tarrytown

3 out of 5
200 West Main Street Elmsford NY
Fully refundableReserve now, pay when you stay
The price is £108 per night from 12 Jul to 13 Jul
£108
12 Jul - 13 Jul
includes taxes & fees
8/10 Very good! (1,541 reviews)
"The hotel loss power it was so hot and unbearable with out power the room was dirty when we arrived spoke with front desk who said it would be handled when we returned that evening the bathroom had not been clean and with the power out no one could come clean it so we were una le to shower"

Reviewed on 5 Jul 2026

Hampton Inn White Plains/Tarrytown
Sonesta White Plains Downtown

Sonesta White Plains Downtown

4 out of 5
66 Hale Ave White Plains NY
Fully refundableReserve now, pay when you stay
The price is £167 per night from 2 Aug to 3 Aug
£167
2 Aug - 3 Aug
includes taxes & fees
8.8/10 Excellent! (1,321 reviews)
"Nicely renovated property."

Reviewed on 4 Jul 2026

Sonesta White Plains Downtown
See all 1,418 properties in Old Greenwich
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.
All Inclusive Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Stay near popular Old Greenwich attractions

Greenwich Point Park

9.2/10 (23 reviews)
This serene coastal park offers panoramic views of Long Island Sound and walking trails through diverse habitats. Explore the historic Innis Arden estate or watch for migratory birds in this Audubon-recognized area.
See properties

Frequently asked questions

Why should I book my Old Greenwich holiday with Expedia?
With top-value airfares, accommodation and car hire choices all in one place, Expedia makes booking your Old Greenwich break hassle-free. What's more, we can help you bundle your bookings into a package holiday so you can get even more savings. Pick from amazing escapes, add flights and/or a hire car (and maybe even some fun tours!) and get unbeatable prices. Need to change plans? Expedia has a flexible cancellation policy for many reservations. To learn more, head over to our Customer Service Portal link.
When is the best time of year to holiday in Old Greenwich?
Old Greenwich is at its busiest in April, May and October. If you want a more laid-back escape, visit in January, March and December. With daytime average temperatures of 0ºC, January is the coolest month in Old Greenwich. The warmest time of year is July, when you can expect average temperatures of 24ºC during the day. Whatever the weather conditions, you'll find loads to keep you entertained here.
What is the top hotel for my holiday in Old Greenwich?
The Inn at Mystic is the perfect base for an epic escape in Old Greenwich, offering all the conveniences you need and more.
How do I get a cheap holiday to Old Greenwich?
Creating your own Old Greenwich holiday with Expedia is a great way to save. We have access to more than 400 air carriers and 321,000 hotel options worldwide. With such a fantastic range to select from, you'll have no trouble putting together your next dream getaway. Learn more about how you can save money on your holiday when you combine your flight and hotel bookings with Expedia.
What should I do on my Old Greenwich holiday?
Ensure your holiday in Old Greenwich is an unforgettable one by checking out its best attractions. Greenwich Avenue, Chelsea Piers, The Glass House and Stamford Town Centre are just some of the things worth discovering while you're in the city.
What is the best area to stay in when on holiday in Old Greenwich?
There's so much to explore in Old Greenwich, so spend your nights near its best sights and maximise your time sightseeing. Greenwich Point Park is one place that should be on your itinerary.
Do I need a visa for my Old Greenwich holiday?
Official government websites have all the information you need on visa requirements, application procedures and any supporting documentation. Your nationality and reason for visiting, whether it be for holidays or work, will determine if you'll need a visa for Old Greenwich. Also check that your passport is up to date and has a minimum of six months validity remaining after your planned date of return. Do all your travel planning well in advance to avoid any last-minute surprises.
What should I wear on my Old Greenwich holiday?
First, think about the types of activities you'll be doing during your Old Greenwich holiday and choose versatile pieces that you can easily mix and match. For fashion inspiration or even information on dress codes, browse a few style blogs or social media accounts. Pack with confidence by monitoring the local weather conditions in Old Greenwich. July brings the warmest temperatures, with daily averages of 24ºC, while January days average 0ºC, making it the coolest time of the year.
What does an Expedia Old Greenwich holiday include?
Much of that depends on you. Simply pick from a variety of Old Greenwich packages, such as a hire car, hotel and flight. You can also book a hotel with a flight, or a car hire and a flight. Once you've made your booking, add on the fun stuff like experiences and activities. Whatever your Old Greenwich holiday looks like, you're sure to save! Private holiday homes and condos are two highly sought-after property types in Old Greenwich. Whatever your preference or size of your group, you can rely on Expedia for the freedom and flexibility to personalise your escape.
Does Expedia offer Book Now, Pay Later Old Greenwich holidays?
Your bank balance shouldn't prevent you from escaping on holiday, so Expedia has devised a solution to help. Thanks to our partnership with online lender Klarna, it's easier than ever to book an incredible getaway without draining your savings. Klarna offers flexible payment options during the checkout process that take the worry out of budgeting for your break. Consider one of these flexible payment options:

  • Pay monthly holidays: Klarna offers convenient monthly payment plans that suit all types of budgets, so you can jet away on that well-deserved holiday sooner.
  • No-deposit holidays: When you come across an incredible deal but your budget doesn't quite go that far, Klarna's no-deposit holiday plan will allow you to Book Now, Pay Later to get what you want.

Can I choose my airline with an Old Greenwich Expedia holiday?
Yes — that's one of the best things about an Expedia holiday package. You're in control. We have access to more than 400 partner airlines all over the world, so you have lots of choice when creating your Old Greenwich trip.

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. Flight-inclusive packages are ATOL protected.