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.
Days Inn by Wyndham Elmsford / White Plains

Days Inn by Wyndham Elmsford / White Plains

2 out of 5
Price was CA $648, price is now CA $551 per person
CA $551
per person
Dec 11 - Dec 13
found 1 day ago
Roundtrip flight included
Toronto (YTO) to White Plains (HPN)
7.4/10 Good! (1,013 reviews)

Stamford Marriott

Stamford Marriott

3.5 out of 5
Downtown Stamford
Price was CA $966, price is now CA $727 per person
CA $727
per person
Dec 17 - Dec 20
found 1 day ago
Roundtrip flight included
Toronto (YTO) to White Plains (HPN)
8/10 Very good! (1,000 reviews)
This is an older property, but it was incredibly convenient for Hertz return and the staff were very helpful in getting us a room on a higher floor. The room was clean.

Reviewed on Oct 29, 2026

Home & Away Hotel-Style

Home & Away Hotel-Style

2 out of 5
West Norwalk
Price was CA $884, price is now CA $727 per person
CA $727
per person
Dec 10 - Dec 13
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to White Plains (HPN)
10/10 Exceptional! (2 reviews)
Newly renovated, nice place

Reviewed on Oct 4, 2026

Stamford Suites

Stamford Suites

4 out of 5
Downtown Stamford
Price was CA $1,319, price is now CA $1,116 per person
CA $1,116
per person
Dec 11 - Dec 15
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to White Plains (HPN)
6.2/10 (197 reviews)
All good

Reviewed on Oct 30, 2026

Luxury NY Home with Free Parking

Luxury NY Home with Free Parking

4 out of 5
Save 100% on your flight
Price was CA $4,678, price is now CA $4,010 per person
CA $4,010
per person
Dec 9 - Dec 13
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to White Plains (HPN)
8/10 Very good! (1 review)
Rooms were very clean, well decorated however bathrooms were not. Parking was accessible and perfect. Some appliances did not work like iron stained my clothes and coffee machine did not work. Everything else was fine.

Reviewed on Nov 8, 2025

Ready to book your vacation to Old Greenwich?

 

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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
The price is CA $322 per night from Nov 19 to Nov 20
CA $322
CA $370 total
Nov 19 - Nov 20
includes taxes & fees
Hyatt Regency Greenwich
LIV Hotel Bronx - Newly Built

LIV Hotel Bronx - Newly Built

3 out of 5
3530 Webster Ave Bronx NY
Fully refundableReserve now, pay when you stay
The price is CA $180 per night from Nov 30 to Dec 1
CA $180
CA $212 total
Nov 30 - Dec 1
includes taxes & fees
LIV Hotel Bronx - Newly Built
Royal Regency Hotel

Royal Regency Hotel

3.5 out of 5
165 Tuckahoe Rd Yonkers NY
Fully refundableReserve now, pay when you stay
The price is CA $158 per night from Nov 8 to Nov 9
CA $158
CA $194 total
Nov 8 - Nov 9
includes taxes & fees
Royal Regency Hotel
See all 1,429 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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Stay near popular Old Greenwich attractions

Greenwich Point Park

9.2/10 (23 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.
See properties

Frequently asked questions

How much does an Old Greenwich vacation package cost?
You'll find cheap prices from CA $551 on Expedia for your Old Greenwich getaway. However, factors like the length of stay, the season and your choice of hotel will determine how much your vacation to Old Greenwich costs.
What are the cheapest months to go to Old Greenwich?
January, February and August are great times to search for cheap Old Greenwich vacation packages. Opting to travel in less busy months means you can generally find reduced prices on flights and hotels.
How many days is enough for Old Greenwich?
Old Greenwich vacations can be short or long, but to get a real feel for this place, we'd say 2 days is a good ballpark. In this timeframe, you can fit in headline attractions like Greenwich Point Park and Bruce Museum of Arts and Science as well as hidden gems. Don't skip cool areas such as Downtown Stamford and Cove - East Side - Shippan either. If you plan wisely, you may even be able to take a day trip from Old Greenwich too.
How to find the best Old Greenwich package deals?
Use Expedia's handy filters to help you find some fabulous Old Greenwich package deals. When you start your search, just set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your adventure for midweek, or browse for Old Greenwich package deals in the off-season. Play around with your travel dates and you may land even better discounts. As a rule of thumb, it's usually best to book your vacation package well in advance.
Is it cheaper to book an Old Greenwich vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your car rental, hotel and flight into one great-value price and you could save hundreds of dollars. You'll typically get a better deal than booking each component individually. And you'll still enjoy the freedom to create a customized Old Greenwich vacation by choosing your preferred accommodation type, airline and car class.
When to book a vacation package to Old Greenwich?
If you have your Old Greenwich travel dates finalized, book early to bag some fantastic deals. With Expedia, you can generally reserve some flights up to one year ahead of time. Prefer spur-of-the-moment adventures? Our last-minute deals are great for jetting off on a whim.
How to plan a trip to Old Greenwich?

  1. Choose the right time to travel: Your schedule, preferred season and the type of weather you like can all influence your decision on when to travel to Old Greenwich.
  2. Set a budget: Factor in expenses such as transportation, flights and meals when calculating how much to put aside for your trip to Old Greenwich. Then, pick a property that suits your budget, whether that's a wallet-friendly option or a more upscale retreat.
  3. Work out your trip length: Consider how much time you'd like to spend discovering Old Greenwich. Plan your days so you can get to all the attractions and activities you're interested in without rushing.
  4. Bundle your accommodations and airfare: After you've nailed down your dates and duration, book the right Old Greenwich vacation package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.