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.
The Stamford Hotel

The Stamford Hotel

3.5 out of 5
Downtown Stamford
Price was CA $1,030, price is now CA $837 per person
CA $837
per person
Oct 15 - Oct 18
found 2 hours ago
Roundtrip flight included
Toronto (YYZ) to White Plains (HPN)
7.8/10 Good! (1,200 reviews)

Modern Comfort in the Heart of NYC

Modern Comfort in the Heart of NYC

4 out of 5
Southeast Yonkers
Price was CA $2,239, price is now CA $1,596 per person
CA $1,596
per person
Oct 22 - Oct 28
found 18 hours ago
Roundtrip flight included
Toronto (YYZ) to White Plains (HPN)
3.6/10 (4 reviews)
It took calling the booking website customer service to get in contact with the host. I end up getting a different property that the one I reserved but the new on was more bedrooms, at the end I work out but it took some long coy with the host.

Reviewed on Jun 29, 2026

Sonesta White Plains Downtown

Sonesta White Plains Downtown

4 out of 5
Price was CA $1,557, price is now CA $1,195 per person
CA $1,195
per person
Sep 7 - Sep 14
found 19 hours ago
Roundtrip flight included
Ottawa (YOW) to White Plains (HPN)
8.8/10 Excellent! (1,326 reviews)

Elegant Hideaway with Free Parking

Elegant Hideaway with Free Parking

2 out of 5
Price was CA $1,161, price is now CA $914 per person
CA $914
per person
Sep 14 - Sep 19
found 15 hours ago
Roundtrip flight included
Toronto (YYZ) to White Plains (HPN)
No reviews

The Opus Westchester, Autograph Collection

The Opus Westchester, Autograph Collection

5 out of 5
Price was CA $2,805, price is now CA $2,270 per person
CA $2,270
per person
Sep 16 - Sep 21
found 13 hours ago
Roundtrip non-stop flight included
Ottawa (YOW) to White Plains (HPN)
9.2/10 Wonderful! (569 reviews)

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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 $292 per night from Aug 10 to Aug 11
CA $292
CA $335 total
Aug 10 - Aug 11
includes taxes & fees
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
The price is CA $221 per night from Aug 16 to Aug 17
CA $221
CA $288 total
Aug 16 - Aug 17
includes taxes & fees
8.2/10 Very good! (1,197 reviews)
"Had a midweek break from the city for two days and wish I could say wife and I would return. Bathroom absolutely disgusting with hairs in shower. Just 2 towels , 1 hand towel and 1 washcloth for 2 people. NO BATHMAT. Asked housekeeping for extra towels and told they were low on supply. SMH....... ..."

Reviewed on Aug 2, 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
The price is CA $184 per night from Aug 16 to Aug 17
CA $184
CA $210 total
Aug 16 - Aug 17
includes taxes & fees
Baymont by Wyndham White Plains - Elmsford
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 $837 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.