Greenwich Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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.
Luxury NYC Home with Free Parking for 12
CA $1,266
per person
Oct 29 - Nov 2
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to White Plains (HPN)
2/10 (1 review)
Place didn't exist. Host did not respond to requests to clarify check-in. Upon arriving, the location was not as described and an individual who answered the door informed our party this was not a rental property. Had to last minute book elsewhere.
Reviewed on Feb 11, 2026
Delamar Southport
CA $1,318
per person
Dec 1 - Dec 5
found 19 hours ago
Roundtrip flight included
Toronto (YYZ) to White Plains (HPN)
9.6/10 Exceptional! (510 reviews)
Loved it! Staff very friendly and helpful, epic breakfast and fun bar scene downstairs.
I feel it’s overpriced or I would have gone with 5 stars.
Reviewed on Sep 15, 2026
Ready to book your vacation to Greenwich?
Greenwich Hotel Deals
Delamar Greenwich Harbor
500 Steamboat Rd Greenwich CT
Fully refundableReserve now, pay when you stay
CA $488
CA $590 total
Sep 27 - Sep 28
includes taxes & fees
9.4/10 Exceptional! (1,000 reviews)
"This hotel, and its staff, was amazing! The restaurant was exceptional! Will definitely stay here again!"
Reviewed on Sep 22, 2026
Private Gazebo on Byram River, Naturally Preserved your own stone deck Greenwich
Greenwich CT
CA $238
CA $316 total
Sep 27 - Sep 28
includes taxes & fees
8/10 Very good! (5 reviews)
"Amazing host I appreciate everything she did for me"
Reviewed on Aug 13, 2026
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.
Stay near popular Greenwich attractions
Greenwich Avenue
9.4/10 (78 reviews)
During your visit to Greenwich, you can search for that perfect souvenir at Greenwich Avenue. Take in the art scene while you're in the area.
Bruce Museum of Arts and Science
8.6/10 (14 reviews)
You can study the exhibits at Bruce Museum of Arts and Science, a museum with a storied past, during your travels to Greenwich. Stroll along the waterfront or experience the art scene in this family-friendly area.
Hawthorne Beach
10.0/10 (1 review)
Why not spend a lazy afternoon at Hawthorne Beach during your trip to Greenwich? Stroll along this romantic area's waterfront, or simply enjoy its restaurants.
Putnam Cottage
7.8/10 (6 reviews)
You can learn about the history of Greenwich when you stop by Putnam Cottage. While in this family-friendly area, you can savor the top-notch restaurants.
Griffith E. Harris Golf Course
8.6/10 (4 reviews)
Enjoy a round of golf in Greenwich at Griffith E. Harris Golf Course. While in this family-friendly area, you can savor the top-notch restaurants.
Wild Flower Sanctuary
You can take time to visit Wild Flower Sanctuary during your travels to Greenwich. Stroll along this romantic area's waterfront, or simply enjoy its restaurants.
Baldwin Farms
You can take time to visit Baldwin Farms during your travels to Greenwich. Stroll along this romantic area's waterfront, or simply enjoy its restaurants.
Stanwich Club
8.6/10 (7 reviews)
Enjoy a round of golf in Greenwich at Stanwich Club. While in this family-friendly area, you can savor the top-notch restaurants.
Frequently asked questions
How much does a Greenwich vacation package cost?
You can pick up a vacation package to this popular destination from CA $876 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?
- 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.
- 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.
- 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.
- 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.
