Greenwich Vacation Packages

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    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
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    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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Your Greenwich Vacation

The stress-free way to experience this interesting city is with a customized Greenwich vacation package. Stay in the neighborhood of Downtown Stamford, which is great for history, bars and pubs and dining or go someplace else — our packages are all about you. If sightseeing is on the agenda during your trip to Greenwich, stop by major attractions like Chelsea Piers, Greenwich Avenue and Stamford Town Center. A couple of clicks is all it takes to build a tailor-made Greenwich vacation on Expedia.

Top Greenwich Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Super 8 by Wyndham Stamford/New York City Area

Super 8 by Wyndham Stamford/New York City Area

2.5 out of 5
West Side
per person
Aug 14 - Aug 18
found 15 hours ago
Roundtrip flight included
Toronto (YYZ) to White Plains (HPN)
6.2/10 (1,006 reviews)
The Super8 was an awesome stay. Staff was polite and helpful with answering our questions...

Reviewed on Jul. 6, 2025

Hilton Stamford Hotel & Executive Meeting Center

Hilton Stamford Hotel & Executive Meeting Center

3.5 out of 5
Waterside
per person
Sep 10 - Sep 14
found 1 day ago
Roundtrip flight included
Toronto (YTO) to White Plains (HPN)
7.4/10 Good! (1,001 reviews)
Shabby desk chair in room, wall paper in room separating at the seams, no remote control for the TV

Reviewed on Jul. 9, 2025

EVEN Hotel Norwalk by IHG

EVEN Hotel Norwalk by IHG

3.5 out of 5
per person
Aug 29 - Sep 1
found 8 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to White Plains (HPN)
8.4/10 Very Good! (1,009 reviews)
there was no coffee in am to get machine down 4 days straight

Reviewed on Jul. 8, 2025

Baymont by Wyndham White Plains - Elmsford

Baymont by Wyndham White Plains - Elmsford

2.5 out of 5
per person
Aug 20 - Aug 24
found 1 day ago
Roundtrip flight included
Toronto (YTO) to White Plains (HPN)
8.2/10 Very Good! (1,373 reviews)
Hotel is clean, modern and well maintained. Staff is friendly and responsive to any issues.

Reviewed on Jul. 9, 2025

Hyatt Regency Greenwich

Hyatt Regency Greenwich

4 out of 5
per person
Sep 1 - Sep 4
found 1 day ago
Roundtrip flight included
Toronto (YTO) to White Plains (HPN)
8.2/10 Very Good! (964 reviews)
Pool was disappointing small too much chlorine

Reviewed on Jul. 8, 2025

Ready to book your vacation to Greenwich?

 

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Greenwich Hotel Deals

Delamar Greenwich Harbor
Delamar Greenwich Harbor
4 out of 5
500 Steamboat Rd, Greenwich, CT
Fully refundableReserve now, pay when you stay
The price is CA $486 per night from Jul 20 to Jul 21
CA $486
CA $579 total
Jul 20 - Jul 21
includes taxes & fees
9.2/10 Wonderful! (919 reviews)
"Great experience. Luxurious room. Great staff."

Reviewed on Jun. 23, 2025

Delamar Greenwich Harbor
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.
Greenwich
The price is CA $245 per night from Jul 14 to Jul 15
CA $245
CA $458 total
Jul 14 - Jul 15
includes taxes & fees
8.6/10 Excellent! (3 reviews)
An idyllic Greenwich retreat, perfect for our family of 4
"George and Subhas home was perfect for our family to spend a weekend in southern Connecticut while in town for the weekend to visit friends. We have two young daughters (age 1 and age 6) and always try to find places to stay where they can have their own room. The rooms were very spacious and clean, ..."

Reviewed on Jun. 29, 2025

2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.
Stanton House Inn
Stanton House Inn
3.5 out of 5
76 Maple Ave, Greenwich, CT
9.6/10 Exceptional! (144 reviews)
"We had the best 2 night stay here after 4 nights in New York. I'd we'd known better we would have stayed here the whole time and used the train to visit New York! It's just the wonderful, especially Katie's avocado toast 😋 thank you all"

Reviewed on Jun. 24, 2025

Get rates
Stanton House Inn
See all 475 properties in 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.

All Inclusive Vacations

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Discover the most popular places to visit in Greenwich

Stanwich Club

Enjoy a round of golf in Greenwich at Stanwich Club. While in this family-friendly area, you can savor the top-notch restaurants.

Stanwich Club

Frequently asked questions

How much does a Greenwich vacation package cost?
You can pick up a vacation package to this popular destination from CA $521 on Expedia. However, how much your vacation to Greenwich costs will depend on your hotel choice, length of stay and season.
What are the cheapest months to go to Greenwich?
If you'd like to book a cheap Greenwich vacation package, consider planning a trip in March, May and October. You're likely to find better prices on hotels and airfares during these months --- ideal for travellers wishing to save money.
How many days is enough for Greenwich?
Greenwich vacations come in many shapes and sizes, but to get a true feel for this destination, we'd say 2 days is about right. In this timeframe, you can visit top sights like Greenwich Point Park and Bruce Museum of Arts and Science along with lesser-known spots. Don't forget to explore neighbourhoods such as Downtown Stamford and Greenwich Municipal Centre Historic District either. If you plan wisely, you can even schedule a day trip outside of Greenwich too.
Is it worth booking a vacation package to Greenwich?
Greenwich has everything you need for an awesome getaway --- coastal beaches, views and golfing are just the start. Whether you'd like to check out sights such as Greenwich Avenue and Bruce Museum of Arts and Science, or take the road less travelled, you'll have plenty to do on your Greenwich vacation.
How to find the best Greenwich package deals?
Start your search for a Greenwich package deal by entering your destination and travel dates under our "Packages" tab. Then add some filters, like "Property type" and "Amenities," to fine-tune the results to your exact needs. You can also sort by "Package discount" and discover offers that come with unbeatable savings. If you don't find the ideal Greenwich package deal right away, simply tweak your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Greenwich escape underway.
Is it cheaper to book a Greenwich vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your hotel, car rental and flight into one great-value price and you could save hundreds of dollars. You'll generally snag a better deal than booking each component individually. And you'll still have the freedom to create a personalized Greenwich vacation by choosing your preferred airline, accommodation type and car class.
When to book a vacation package to Greenwich?
If you're planning a spur-of-the-moment Greenwich trip, check out our last-minute deals that can be booked up to a week before you go. Prefer not to wait until the last minute? You can score sensational deals on your hotels and flights by booking ahead.
How to plan a trip to Greenwich?

  1. Pick the ideal time to travel: Your schedule, favourite season and the type of weather you enjoy can all influence your decision on when to visit Greenwich.
  2. Plan your budget wisely: Besides the price of your accommodations, you'll need to factor in other expenses too. These include transportation, food and flights. Also, put aside a little extra for unexpected costs that may crop up during your trip to Greenwich.
  3. Decide your trip length: Think about how much time you'd like to spend discovering Greenwich. Plan your days so you can get to all the experiences and attractions you're interested in at a comfortable pace.
  4. Combine your accommodations and airfare: Once you've nailed down your trip dates and duration, lock in the right 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.