Old Greenwich Vacations from $310

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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.
Amsterdam Hotel

Amsterdam Hotel

2 out of 5
Downtown Stamford
per person
Sep 15 - Sep 20
found 1 day ago
Roundtrip flight included
Miami (MIA) to White Plains (HPN)
8.4/10 Very Good! (1,624 reviews)
The Amsterdam is an average hotel. Try to avoid rooms on the south side as they face I-95 and you can hear the noise from the road. The continental breakfast goes quickly, so get there early if you want it.

Reviewed on Aug 5, 2025

Tarrytown House Estate

Tarrytown House Estate

3.5 out of 5
per person
Sep 20 - Sep 24
found 10 hours ago
Roundtrip flight included
Los Angeles (LAX) to White Plains (HPN)
8/10 Very Good! (1,000 reviews)
The staff was very welcoming and let me check in early. I also needed a few other things and the front desk helped out. The grounds were nice with flowers and lush grass. The room was very noisy. You could hear people above stomping/ walking around all hours. Didn’t get much sleep. You could hear people talking in the hallways. The room was older all the facilities had an old, musty smell. This place needs a makeover. Would be a beautiful place again if updated.

Reviewed on Aug 3, 2025

Global Luxury Suites White Plains

Global Luxury Suites White Plains

3.5 out of 5
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to White Plains (HPN)
6.8/10 (31 reviews)
Nice view from the apartment and great for business trip.

Reviewed on Dec 16, 2024

Luxury NY Home 3BR with Easy Parking

Luxury NY Home 3BR with Easy Parking

3 out of 5
Southeast Yonkers
Save 100% on your flight
per person
Sep 15 - Sep 19
found 1 hour ago
Roundtrip flight included
Miami (MIA) to White Plains (HPN)
3/10 (4 reviews)
Hampton Inn White Plains/Tarrytown

Hampton Inn White Plains/Tarrytown

3 out of 5
per person
Sep 11 - Sep 14
found 16 hours ago
Roundtrip flight included
Dallas (DFW) to White Plains (HPN)
8/10 Very Good! (1,085 reviews)
Great place to stay. Breakfast was good. Easy access to Highways.

Reviewed on Aug 5, 2025

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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
$175 nightly
The price is $201 total per night from Aug 31 to Sep 1
$201 total
Aug 31 - Sep 1
Total includes taxes and fees
8/10 Very Good! (1,015 reviews)
7 year anniversary trip
"Room was spotless, bed was comfortable, front desk was super friendly. The cleaners were super nice every morning. The pool/hot tub was a nice touch. Highly recommend to anyone looking to stay in the area."

Reviewed on Aug 3, 2025

Hyatt Regency Greenwich
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
$148 nightly
The price is $169 total per night from Aug 24 to Aug 25
$169 total
Aug 24 - Aug 25
Total includes taxes and fees
8.2/10 Very Good! (1,392 reviews)
"The rooms were large & bright. Bathroom too- Had elevator. Nice breakfast area. Great value for the money no matter part of country that we choose a Baymont Hotel."

Reviewed on Aug 4, 2025

Baymont by Wyndham White Plains - Elmsford
Royal Regency Hotel

Royal Regency Hotel

3.5 out of 5
165 Tuckahoe Rd, Yonkers, NY
Fully refundableReserve now, pay when you stay
$108 nightly
The price is $127 total per night from Aug 21 to Aug 22
$127 total
Aug 21 - Aug 22
Total includes taxes and fees
8.2/10 Very Good! (2,200 reviews)
"I love this place and the staff ! Excellent place to stay !! It’s very clean and the area is quiet and nice ! The staff are awesome ."

Reviewed on Aug 6, 2025

Royal Regency Hotel
See all 1,294 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 $310 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.