Old Greenwich Vacations from $418

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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.
Hotel NoMa, Trademark Collection by Wyndham

Hotel NoMa, Trademark Collection by Wyndham

3 out of 5
Save 100% on your flight
Price was $560, price is now $418 per person
$418
per person
Nov 14 - Nov 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to White Plains (HPN)
8/10 Very Good! (1,003 reviews)
What a Gem. The room spacious and clean ( tub definitely needs elbow grease but that’s why shower shoes are a thing). Overall, The entire team was amazing. It’s a resort like feeling North of Manhattan. THE FOOD OMG where to begin nothing let me down over the four nights!!!! Dominique, Nicole, and Teddy-and the locals who frequent are the reasons we will come back - NOMA SOCIAL just continue to play a variety of music becasue although I love my latin music it was overkill and DJ’s must represent rhe NYC culture to entirely with a good mix and not a centered focus on one genre- BUT STILL A FAVORITE PLACE!!

Reviewed on Aug 20, 2025

Tarrytown House Estate

Tarrytown House Estate

3.5 out of 5
Price was $1,017, price is now $746 per person
$746
per person
Oct 30 - Nov 3
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to White Plains (HPN)
8/10 Very Good! (1,003 reviews)
Incredible place, from the outdoor seating areas, to the restaurant and bar, the pool, this place is absolutely incredible.

Reviewed on Aug 19, 2025

Hilton Garden Inn Fishkill

Hilton Garden Inn Fishkill

3 out of 5
Save 100% on your flight
Price was $573, price is now $442 per person
$442
per person
Oct 29 - Nov 3
found 3 hours ago
Roundtrip flight included
Tampa (TPA) to White Plains (HPN)
8.6/10 Excellent! (1,001 reviews)
Good location. Comfortable stay.

Reviewed on Aug 9, 2025

Stamford Marriott Hotel & Spa

Stamford Marriott Hotel & Spa

3.5 out of 5
Downtown Stamford
Save 100% on your flight
Price was $609, price is now $470 per person
$470
per person
Nov 14 - Nov 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to White Plains (HPN)
8/10 Very Good! (1,000 reviews)
Great service, very accommodating

Reviewed on Aug 19, 2025

Americas Best Value Inn New Paltz

Americas Best Value Inn New Paltz

2 out of 5
Save 100% on your flight
Price was $638, price is now $496 per person
$496
per person
Oct 29 - Nov 3
found 3 hours ago
Roundtrip flight included
Tampa (TPA) to White Plains (HPN)
8.8/10 Excellent! (1,005 reviews)
Very strict about their check in time. We were 10 minutes early and they made us wait. Otherwise a good experience .

Reviewed on Aug 21, 2025

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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
$206 nightly
The price is $237 total per night from Sep 11 to Sep 12
$237 total
Sep 11 - Sep 12
Total with taxes and fees
8.2/10 Very Good! (1,008 reviews)
"Nice"

Reviewed on Aug 22, 2025

Hyatt Regency Greenwich
Royal Regency Hotel

Royal Regency Hotel

3.5 out of 5
165 Tuckahoe Rd, Yonkers, NY
Fully refundableReserve now, pay when you stay
$113 nightly
The price is $133 total per night from Sep 1 to Sep 2
$133 total
Sep 1 - Sep 2
Total with taxes and fees
8.2/10 Very Good! (2,213 reviews)
"Room was nice and clean. It’s in residential area right front of private homes. Was bet noisy. Overall I was satisfied. Staff was friendly."

Reviewed on Aug 22, 2025

Royal Regency Hotel
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
$127 nightly
The price is $145 total per night from Sep 1 to Sep 2
$145 total
Sep 1 - Sep 2
Total with taxes and fees
7.8/10 Good! (1,128 reviews)
Good hotel but rude guests
"The staff were very nice and helpful. The room could do with a refresh but was clean and comfortable. The noise from the roads outside was loud making sleep harder. The dog barking on one side and the constant arguing on the other side didn't help. More soundproofing would be nice. Breakfast and ..."

Reviewed on Aug 22, 2025

Hampton Inn White Plains/Tarrytown
See all 1,302 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.

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Frequently asked questions

How much does an Old Greenwich vacation package cost?
Offering great value package deals from $418 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.