Old Greenwich Vacations from $166

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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.

The Latest Old Greenwich vacation packages

Price found within the past 48 hours. Click for updated prices.
Courtyard by Marriott Poughkeepsie

Courtyard by Marriott Poughkeepsie

3 out of 5
Save 100% on your flight
Price was $241, price is now $166 per person
$166
per person
Mar 16 - Mar 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to White Plains (HPN)
8.8/10 Excellent! (1,002 reviews)
Clean. Parking. Service of front desk!

Reviewed on Jan 8, 2026

Hampton Inn & Suites Yonkers

Hampton Inn & Suites Yonkers

2.5 out of 5
Northwest Yonkers
Save 100% on your flight
Price was $359, price is now $229 per person
$229
per person
Mar 28 - Mar 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to White Plains (HPN)
8.2/10 Very Good! (1,621 reviews)
Yeah, the breakfast was it was good

Reviewed on Jan 7, 2026

Residence Inn by Marriott Yonkers Westchester County

Residence Inn by Marriott Yonkers Westchester County

3 out of 5
Northwest Yonkers
Save 100% on your flight
Price was $541, price is now $368 per person
$368
per person
Feb 20 - Feb 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to White Plains (HPN)
8.6/10 Excellent! (952 reviews)
Nice, quite, clean, and spacious. Much better than the tiny rooms in Manhattan. Close to freeway with easy access to NYC, Westchester, and Jersey. Free breakfast was also pretty decent and the staff was helpful.

Reviewed on Jan 8, 2026

Spacious 3BR Luxe Escape near NYC

Spacious 3BR Luxe Escape near NYC

2 out of 5
Southeast Yonkers
Save 100% on your flight
Price was $589, price is now $405 per person
$405
per person
Feb 13 - Feb 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to White Plains (HPN)
No reviews
Tarrytown House Estate

Tarrytown House Estate

3.5 out of 5
Price was $837, price is now $603 per person
$603
per person
Mar 28 - Apr 4
found 11 hours ago
Roundtrip flight included
Los Angeles (LAX) to White Plains (HPN)
8/10 Very Good! (1,001 reviews)
Lovely grounds. It was nice that there is a good restaurant on the grounds as well.

Reviewed on Jan 2, 2026

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Discover the most popular places to visit in Old Greenwich

Greenwich Point Park

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.

Greenwich Point Park

Old Greenwich Hotel Deals

Hyatt Regency Greenwich

Hyatt Regency Greenwich

4 out of 5
1800 E Putnam Avenue Old Greenwich CT
Fully refundableReserve now, pay when you stay
$186 nightly
The price is $214 total per night from Jan 23 to Jan 24
$214 total
Jan 23 - Jan 24
Total with taxes and fees
8.4/10 Very Good! (1,000 reviews)
I had an amazing experience! The room was clean, the staff were very kind and the food was great.

Reviewed on Jan 6, 2026

Hyatt Regency Greenwich
EVEN Hotel Norwalk by IHG

EVEN Hotel Norwalk by IHG

3.5 out of 5
426 Main Ave, Route 7 Norwalk CT
Fully refundableReserve now, pay when you stay
$111 nightly
The price is $128 total per night from Feb 9 to Feb 10
$128 total
Feb 9 - Feb 10
Total with taxes and fees
8.2/10 Very Good! (1,046 reviews)
I stay here every month I come to CT--safe, great bed, great staff, reliable and not expensive--what more can you want?

Reviewed on Jan 5, 2026

EVEN Hotel Norwalk by IHG
Hampton Inn Garden City Long Island

Hampton Inn Garden City Long Island

2.5 out of 5
1 North Ave Garden City NY
Fully refundableReserve now, pay when you stay
$118 nightly
The price is $132 total per night from Feb 8 to Feb 9
$132 total
Feb 8 - Feb 9
Total with taxes and fees
8.4/10 Very Good! (1,044 reviews)
Clean areas and staff are friendly

Reviewed on Jan 5, 2026

Hampton Inn Garden City Long Island
See all 1,447 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.

Find the Best Old Greenwich Vacation Packages

Old Greenwich Essential Information

Language
English
Currency
U.S dollars
Closest Airport
John F. Kennedy Intl. Airport (JFK)
Population
6,600
Max Temp Winter
35ºF
Max Temp Summer
80ºF
Top Sights
Norwalk Maritime Aquarium, Compo Beach and The Maritime Aquarium

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Frequently asked questions

How much does an Old Greenwich vacation package cost?
Offering great value package deals from $166 on Expedia, you'll be pleasantly surprised at how much a vacation to Old Greenwich costs! Our packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Old Greenwich?
You can usually find lower rates and greater availability in January, March and December. Browse our cheap Old Greenwich vacation packages and you could land some great off-season deals.
How many days is enough for Old Greenwich?
With a well-planned itinerary, you can easily tick off the main Old Greenwich sights in a handful of days. But if you want to discover hidden spots or take day trips, think about booking your Old Greenwich vacation for longer.
How to find the best Old Greenwich package deals?
Finding a cheap Old Greenwich package deal is a cinch with Expedia. After you've entered your trip dates and destination under our "Packages" tab, set your maximum budget, apply a couple of filters and browse what's available. You can tweak your search by "Area," "Amenities," "Property type" and more. Sort the results by "Price: low to high" to discover the most pocket-friendly Old Greenwich package deals. Want a simple trick to score even more savings? Be flexible with your departure dates and consider going away on a weekday, when prices are often lower.
Is it cheaper to book an Old Greenwich vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your flight, car rental and hotel into one great-value price and you could save hundreds of dollars. You'll generally get a better deal than booking each component individually. And you'll still get the freedom to create a personalized Old Greenwich vacation by choosing your favorite accommodation type, airline and car class.
When to book a vacation package to Old Greenwich?
If you've got your Old Greenwich travel dates finalized, book as soon as you can to snap up some incredible deals. With Expedia, you can often reserve some flights up to one year in advance. Prefer spur-of-the-moment trips? Our last-minute deals are perfect for quick escapes.
Does Expedia offer Book Now, Pay Later Old Greenwich vacation packages?
Jet off on your perfect trip to Old Greenwich with help from our Book Now, Pay Later vacations. No need to scrimp and save or wait until the next payday — we've teamed up with online lender Affirm to give you flexibility with your finances. Our vacation packages with payment plans mean you can spread the cost over 3, 6 or 12 months. With no hidden or late payment fees, it's a breeze to budget for your trip and snap up cheap deals before they disappear.

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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.