Old Greenwich Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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    Save up to CA $775 when you book a flight and hotel together*
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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

Prices and availability subject to change. Additional terms may apply.
Luxury NY Home 3BR with Easy Parking

Luxury NY Home 3BR with Easy Parking

3 out of 5
Southeast Yonkers
Save 100% on your flight
per person
Jun. 6 - Jun. 10
Roundtrip flight included
Ottawa (YOW) to White Plains (HPN)
No reviews
Modern Luxury Home w GameRoom & Parking

Modern Luxury Home w GameRoom & Parking

3 out of 5
Southeast Yonkers
Save 100% on your flight
per person
Jun. 3 - Jun. 8
Roundtrip non-stop flight included
Calgary (YYC) to White Plains (HPN)
10/10 Exceptional! (1 review)
This was an excellent House My birthday weekend was amazing I totally would book again

Reviewed on Mar. 17, 2024

Sleepy Hollow Hotel

Sleepy Hollow Hotel

3.5 out of 5
per person
Jul. 12 - Jul. 16
Roundtrip flight included
Toronto (YYZ) to White Plains (HPN)
6.8/10 (1,004 reviews)
I love this place. Always clean with a friendly staff.

Reviewed on Apr. 19, 2024

Hyatt Regency Greenwich

Hyatt Regency Greenwich

4 out of 5
per person
Jun. 8 - Jun. 11
Roundtrip flight included
Toronto (YTO) to White Plains (HPN)
7.8/10 Good! (1,003 reviews)
Hopefully once renovations are complete it improves.

Reviewed on Apr. 21, 2024

Sonesta White Plains Downtown

Sonesta White Plains Downtown

4 out of 5
per person
Jun. 27 - Jul. 1
Roundtrip flight included
Montreal (YUL) to White Plains (HPN)
8.4/10 Very Good! (1,091 reviews)
I found my room very clean and quiet. Most importantly it was close to everything I needed to actual walk because I did not have my own vehicle to get around 😊

Reviewed on Apr. 4, 2024

Old Greenwich Hotel Deals

Hyatt Regency Greenwich
Hyatt Regency Greenwich
4 out of 5
1800 E Putnam Avenue, Old Greenwich, CT
Fully refundable
The price is CA $258 per night from Apr. 28 to Apr. 29
CA $258
CA $296 total
includes taxes & fees
Apr 28 - Apr 29
7.8/10 Good! (1,007 reviews)
Wonderful hotel
"We have stayed at the Hyatt Regency for several year while visiting family. While we only sleep and shower at the hotel, we have never been disappointed by the condition of our rooms or the customer service."

Reviewed on Apr. 16, 2024

Hyatt Regency Greenwich
Royal Regency Hotel
Royal Regency Hotel
3.5 out of 5
165 Tuckahoe Rd, Yonkers, NY
Fully refundableReserve now, pay when you stay
The price is CA $191 per night from Apr. 30 to May 1
CA $191
CA $246 total
includes taxes & fees
Apr 30 - May 1
8/10 Very Good! (1,403 reviews)
"good"

Reviewed on Apr. 23, 2024

Royal Regency Hotel
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 $171 per night from May 12 to May 13
CA $171
CA $196 total
includes taxes & fees
May 12 - May 13
8/10 Very Good! (1,000 reviews)
"Great experience"

Reviewed on Apr. 22, 2024

Baymont by Wyndham White Plains - Elmsford
See all 1,114 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.

Explore other types of vacation packages

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does an Old Greenwich vacation package cost?
The most affordable Old Greenwich vacation package is CA $732, so your dream escape can become a reality — without it costing a fortune. Combine flights, hotels and car rentals to tailor make a package that suits your travel style.
How do I get a cheap travel package to Old Greenwich?
Booking a hotel and flight together with Expedia won’t just save you time — it’ll save you a few dollars too. An Old Greenwich vacation package makes it easy to create your ideal trip. With more than 550 airlines throughout the world to choose from, finding convenient flights that fit your busy schedule will be no sweat. Not only that, we have over 1,000,000 properties globally to choose from. Talk about choice! Whatever your budget, Expedia puts the world within your reach.
Where should I stay in Old Greenwich?
A vacation in Old Greenwich isn’t complete without visiting Stamford Town Center, Greenwich Point Park and Stamford Center for the Arts. Spend your nights near these tourist attractions and make sightseeing easy.
What are the top hotels in Old Greenwich?
Hyatt Regency Greenwich and Spacious Beach House That . Huge Yard are two of the most sought-after properties in Old Greenwich. Why not look up the rates and amenities at each and then make up your mind?
How far in advance should I book my Old Greenwich vacation?
Reward yourself with the widest variety at the lowest prices by booking your adventure to Old Greenwich early. Air carriers typically advertise flights around a year prior to departure, so secure your spot as soon as you can. Having said that, Expedia is dedicated to providing you with the best bargains around, so it’s always a good time to book your dream vacation!
What does an Expedia Old Greenwich travel package include?
From hotels and airfares to car rentals, Expedia can help you create an Old Greenwich package that’s right for you. Vacationing for a while? Look into a hotel, rental car and flight bundle. If you’re taking a quick break, a flight and hotel deal may suit you better. Activities can also be added once you’ve made your booking. Our travel packages make it a cinch to save and plan.
What should I know before booking an Old Greenwich travel package?
So many places to travel to, so many things to see and do. With a package, you’ll be able to tick more of them off your list. Bundle your hotels, flights and rental cars and land big savings.
Can I choose my airline with an Old Greenwich Expedia vacation package?
With a vacation package, you’re always in charge. Whether you’re looking to fly to Old Greenwich in first class or coach, simply choose from the available airline options. Expedia has access to over 550 airline partners worldwide.
If I'm not able to travel, can I cancel my Old Greenwich vacation package?
Whether it’s your hotel or flight, you can cancel or change it. Booked your Old Greenwich vacation package in the last 24 hours? You may be able to make changes for free. For bookings made more than 24 hours ago, you may incur a charge from your hotel, airline or car rental company. For more information, visit our Customer Service Portal. We’re here to help you each step of the way.

Discover the most popular places to visit in Old Greenwich

Image for Greenwich Point Park

Greenwich Point Park

Explore the great outdoors at Greenwich Point Park, a lovely green space in Old Greenwich. While in this family-friendly area, you can savor the top-notch restaurants.

Greenwich Point Park
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.