Old Greenwich Vacation Packages
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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.
Top Old Greenwich Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Tarrytown House Estate
Price was CA $1,043, price is now CA $773 per person
CA $773
per person
Aug 24 - Aug 28
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to White Plains (HPN)
8.2/10 Very Good! (1,109 reviews)
Property was beautiful everywhere we looked. Pool was clean and staff was attentive. Nice and well behaved crowd, except in the end a few loud kids that were playing rough (I believe it was an exception). Nice views, clean and comfy room, easy check in/out. Minor complaints: giant chess game needs maintenance, one of the umbrellas in the pool was broken and it took a while until someone took it away (it felt and it could hurt someone). Id love more food options in the front desk (ran out of ice cream and other stuff). Gym and sauna also great, we played a lot of pickeball. Fun!!
Reviewed on Jun 15, 2026
Stamford Suites
Downtown Stamford
Price was CA $1,674, price is now CA $1,293 per person
CA $1,293
per person
Jul 23 - Jul 30
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to White Plains (HPN)
6.4/10 (123 reviews)
Great location, friendly and helpful staff. Good value for money.
Reviewed on Jun 14, 2026
Luxury 3BR Family Home Game Room Parking
Bryn Mawr
Price was CA $7,721, price is now CA $6,073 per person
CA $6,073
per person
Jul 24 - Jul 29
found 21 hours ago
Roundtrip flight included
Toronto (YYZ) to White Plains (HPN)
6.8/10 (3 reviews)
Beautiful layout. Property had everything that was needed for an awesome stay.
Reviewed on Feb 27, 2026
Modern Luxury Home w GameRoom & Parking
Southeast Yonkers
Price was CA $6,619, price is now CA $5,211 per person
CA $5,211
per person
Jul 24 - Jul 29
found 21 hours ago
Roundtrip flight included
Toronto (YYZ) 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
Old Greenwich Hotel Deals
Hyatt Regency Greenwich
1800 E Putnam Avenue Old Greenwich CT
Fully refundableReserve now, pay when you stay
The price is CA $348 per night from Jun 28 to Jun 29
CA $348
CA $401 total
Jun 28 - Jun 29
includes taxes & fees
8.6/10 Excellent! (1,033 reviews)
"The staff was fantastic! A-Z everything was terrific about the hotel. Thanks!"
Reviewed on Jun 15, 2026
Baymont by Wyndham White Plains - Elmsford
540 Saw Mill River Rd Elmsford NY
Fully refundableReserve now, pay when you stay
The price is CA $213 per night from Jun 21 to Jun 22
CA $213
CA $243 total
Jun 21 - Jun 22
includes taxes & fees
8.4/10 Very Good! (1,729 reviews)
"The room smelled musty. The walls were thin so I heard a lot hallway noise and noise from neighboring rooms."
Reviewed on Jun 14, 2026
Tarrytown House Estate
49 E Sunnyside Lane Tarrytown NY
Fully refundableReserve now, pay when you stay
The price is CA $183 per night from Jun 30 to Jul 1
CA $183
CA $260 total
Jun 30 - Jul 1
includes taxes & fees
8.2/10 Very Good! (1,126 reviews)
"I found a mysterious yellow pill on the floor of our hotel room, where my two babies were staying with me and my husband. The hotel knew that I was traveling with babies, as I called 5x to make sure we were all set with their crib beds and early check in. I am extremely disappointed that our safety ..."
Reviewed on Jun 15, 2026
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.
Stay near popular Old Greenwich attractions
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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.
