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.
EVEN Hotel Norwalk by IHG

EVEN Hotel Norwalk by IHG

3.5 out of 5
per person
Oct 13 - Oct 16
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to White Plains (HPN)
8.4/10 Very Good! (1,009 reviews)
The theme of this hotel is wellness and it's awesome. You walk in and they have ginger lime water, lemon water, and regular water to drink. The rooms are equipped with exercise bands, yoga mat and block, and a foam roller. The gym was large and well equipped and kept at a cool temperature. The lighting in the room is soft. There is an outdoor courtyard and a spacious area inside for eating and getting work done. Overall one of the best hotels I've stayed at and would highly recommend.

Reviewed on Jul. 25, 2025

Hilton Stamford Hotel & Executive Meeting Center

Hilton Stamford Hotel & Executive Meeting Center

3.5 out of 5
Waterside
per person
Oct 17 - Oct 21
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to White Plains (HPN)
7.4/10 Good! (1,001 reviews)
Clean, comfortable and super quiet! Staff was very friendly and helpful

Reviewed on Jul. 15, 2025

Hyatt Place Poughkeepsie / Hudson Valley

Hyatt Place Poughkeepsie / Hudson Valley

3 out of 5
Crown Heights
per person
Aug 30 - Sep 2
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to White Plains (HPN)
8.8/10 Excellent! (1,001 reviews)
My Room smelled a little sweaty. Other than that my stay was amazing.

Reviewed on Jul. 17, 2025

Hyatt Regency Greenwich

Hyatt Regency Greenwich

4 out of 5
per person
Aug 29 - Sep 1
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to White Plains (HPN)
8.2/10 Very Good! (964 reviews)
I enjoyed my quick staycation at this property. It is very close to Stamford which has endless amenities. The property looks like a resort, I was very pleased to stay here. I would definitely revisit.

Reviewed on Jul. 23, 2025

Hampton Inn & Suites Yonkers - Westchester

Hampton Inn & Suites Yonkers - Westchester

2.5 out of 5
Northeast Yonkers
per person
Oct 9 - Oct 13
found 1 day ago
Roundtrip flight included
Toronto (YTO) to White Plains (HPN)
8.8/10 Excellent! (1,000 reviews)
My stay here has been easy. The staff has been friendly, and helpful.

Reviewed on Jul. 20, 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 $254 per night from Aug 10 to Aug 11
CA $254
CA $292 total
Aug 10 - Aug 11
includes taxes & fees
8/10 Very Good! (997 reviews)
"I enjoyed my quick staycation at this property. It is very close to Stamford which has endless amenities. The property looks like a resort, I was very pleased to stay here. I would definitely revisit."

Reviewed on Jul. 23, 2025

Hyatt Regency Greenwich
Red Roof Inn PLUS+ Long Island - Garden City

Red Roof Inn PLUS+ Long Island - Garden City

2.5 out of 5
699 Dibblee Drive, Westbury, NY
Fully refundableReserve now, pay when you stay
The price is CA $184 per night from Jul 27 to Jul 28
CA $184
CA $205 total
Jul 27 - Jul 28
includes taxes & fees
7/10 Good! (1,323 reviews)
"The location was perfect for my needs. The room was pristine. The double bed provided ample comfort."

Reviewed on Jul. 20, 2025

Red Roof Inn PLUS+ Long Island - Garden City
EVEN Hotel Norwalk by IHG

EVEN Hotel Norwalk by IHG

3.5 out of 5
426 Main Ave, Route 7, Norwalk, CT
Fully refundable
The price is CA $165 per night from Aug 3 to Aug 4
CA $165
CA $190 total
Aug 3 - Aug 4
includes taxes & fees
8.2/10 Very Good! (1,019 reviews)
Clean and comfortable
"I love to even Hotel I typically stay in them wherever they're available that I'm traveling to."

Reviewed on Jul. 24, 2025

EVEN Hotel Norwalk by IHG
See all 1,292 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?
You'll find cheap prices from CA $556 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.