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.
Stamford Suites

Stamford Suites

4 out of 5
Downtown Stamford
Price was CA $1,457, price is now CA $1,174 per person
CA $1,174
per person
Sep 9 - Sep 14
found 1 day ago
Roundtrip flight included
Toronto (YTO) to White Plains (HPN)
6.4/10 (134 reviews)
This one is like stepping back into the 80s. Old worn out carpet, room smells, the elevator is worse than a service elevator. The room insulation is poor. I was on the 6th floor and heard everything on the road below and from the adjacent room. The breakfast was so bad, I cant even begin. Never staying there again.

Reviewed on Jul 15, 2026

Delamar Southport

Delamar Southport

4 out of 5
Price was CA $2,090, price is now CA $1,610 per person
CA $1,610
per person
Sep 9 - Sep 14
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to White Plains (HPN)
9.6/10 Exceptional! (487 reviews)
Wow, hidden gem. Place is amazing, rooms are well appointed and stylish. Restaurant is phenomenal and the staff from your car pulling up to checkout is superior.

Reviewed on Jul 13, 2026

Luxury NY Home 3BR with Easy Parking

Luxury NY Home 3BR with Easy Parking

3 out of 5
Southeast Yonkers
Price was CA $3,995, price is now CA $3,293 per person
CA $3,293
per person
Sep 3 - Sep 7
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to White Plains (HPN)
3/10 (4 reviews)

Delamar Greenwich Harbor

Delamar Greenwich Harbor

4 out of 5
Price was CA $2,701, price is now CA $2,284 per person
CA $2,284
per person
Sep 3 - Sep 7
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to White Plains (HPN)
9.4/10 Exceptional! (992 reviews)
Beautiful hotel, friendly and attentive staff, great restaurant, but one of the most uncomfortable mattresses I’ve ever slept on. The uncomfortable bed was the only negative.

Reviewed on Jul 15, 2026

Luxury NY Home with Free Parking

Luxury NY Home with Free Parking

4 out of 5
Price was CA $4,814, price is now CA $4,139 per person
CA $4,139
per person
Sep 3 - Sep 7
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) 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 $298 per night from Aug 16 to Aug 17
CA $298
CA $343 total
Aug 16 - Aug 17
includes taxes & fees
Hyatt Regency Greenwich
Sonesta White Plains Downtown

Sonesta White Plains Downtown

4 out of 5
66 Hale Ave White Plains NY
Fully refundableReserve now, pay when you stay
The price is CA $234 per night from Aug 16 to Aug 17
CA $234
CA $314 total
Aug 16 - Aug 17
includes taxes & fees
8.8/10 Excellent! (1,333 reviews)
"Overall great stay. Food, bar, staff, room all nice"

Reviewed on Jul 13, 2026

Sonesta White Plains Downtown
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 $217 per night from Aug 2 to Aug 3
CA $217
CA $300 total
Aug 2 - Aug 3
includes taxes & fees
8.2/10 Very good! (1,173 reviews)
"Room was very clean. Refrigerator was noisy. Price was great."

Reviewed on Jul 13, 2026

Tarrytown House Estate
See all 1,417 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 $1,174 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.

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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.