Old Greenwich Vacations from $384

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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.
Hampton Inn & Suites Yonkers

Hampton Inn & Suites Yonkers

2.5 out of 5
Northwest Yonkers
Save 100% on your flight
Price was $541, price is now $384 per person
$384
per person
Sep 10 - Sep 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to White Plains (HPN)
8.4/10 Very Good! (1,905 reviews)
Clean room, amazing staff ,

Reviewed on Jun 20, 2026

Modern Luxury Home w GameRoom & Parking

Modern Luxury Home w GameRoom & Parking

3.5 out of 5
Southeast Yonkers
Save 100% on your flight
Price was $4,220, price is now $2,988 per person
$2,988
per person
Aug 4 - Aug 9
found 15 hours ago
Roundtrip flight included
Dallas (DFW) to White Plains (HPN)
5.6/10 (8 reviews)
This was an excellent House My birthday weekend was amazing I totally would book again

Reviewed on Mar 17, 2024

Hyatt Place New York/Yonkers

Hyatt Place New York/Yonkers

3 out of 5
Southeast Yonkers
Save 100% on your flight
Price was $1,000, price is now $760 per person
$760
per person
Sep 8 - Sep 15
found 5 hours ago
Roundtrip flight included
Atlanta (ATL) to White Plains (HPN)
9.2/10 Wonderful! (1,477 reviews)
My daughters and granddaughter were disappointed there wasn't a pool that was listed online.

Reviewed on Jun 17, 2026

Delamar Southport

Delamar Southport

4 out of 5
Save 100% on your flight
Price was $990, price is now $753 per person
$753
per person
Aug 9 - Aug 14
found 1 day ago
Roundtrip flight included
Dallas (DFW) to White Plains (HPN)
9.6/10 Exceptional! (482 reviews)
Very clean, friendly staff. Nice breakfast buffet. Close to local universities!

Reviewed on Jun 18, 2026

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Discover the most popular places to visit in Old Greenwich

Greenwich Point Park

5/5(2 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.

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
$229 nightly
The price is $263 total per night from Jul 12 to Jul 13
$263 total
Jul 12 - Jul 13
Total with taxes and fees
8.6/10 Excellent! (1,032 reviews)
"I rarely leave negative reviews, but this stay was disappointing from start to finish. Upon arrival with seven pieces of luggage, not a single staff member offered assistance. I had to find a luggage cart, load everything myself, and transport it through the hotel alone. The most concerning incident ..."

Reviewed on Jun 20, 2026

Hyatt Regency Greenwich
Tarrytown House Estate

Tarrytown House Estate

3.5 out of 5
49 E Sunnyside Lane Tarrytown NY
Fully refundableReserve now, pay when you stay
$163 nightly
The price is $186 total per night from Jun 30 to Jul 1
$186 total
Jun 30 - Jul 1
Total with taxes and fees
8.2/10 Very Good! (1,124 reviews)
"Really beautiful grounds and historic looking get away. Close to town parks and hiking. Nice pool area also"

Reviewed on Jun 21, 2026

Tarrytown House Estate
Baymont by Wyndham White Plains - Elmsford

Baymont by Wyndham White Plains - Elmsford

2.5 out of 5
540 Saw Mill River Rd Elmsford NY
Fully refundableReserve now, pay when you stay
$135 nightly
The price is $155 total per night from Jun 28 to Jun 29
$155 total
Jun 28 - Jun 29
Total with taxes and fees
8.4/10 Very Good! (1,719 reviews)
"Everybody was so friendly. The breakfast was hot and playful. Room was comfortable beds with freezing cold air. Everything we could’ve asked for."

Reviewed on Jun 21, 2026

Baymont by Wyndham White Plains - Elmsford
See all 1,422 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 $384 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.