New Canaan Trips (flight + hotel)

Photo by Marina Timo

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Top hotels in New Canaan

Hampton Inn White Plains/Tarrytown

Hampton Inn White Plains/Tarrytown

3 out of 5
200 West Main Street, Elmsford, NY
Fully refundableReserve now, pay when you stay
The price is P7,231 per night from Sep 1 to Sep 2
P7,231
P8,271 total
Sep 1 - Sep 2
includes taxes & fees
7.8/10 Good! (1,095 reviews)
"Great place to stay. Breakfast was good. Easy access to Highways."

Reviewed on Aug 5, 2025

Hampton Inn White Plains/Tarrytown
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 P8,202 per night from Aug 17 to Aug 18
P8,202
P9,381 total
Aug 17 - Aug 18
includes taxes & fees
8.2/10 Very Good! (1,390 reviews)
"Super comfy bed breakfast was great"

Reviewed on Aug 7, 2025

Baymont by Wyndham White Plains - Elmsford
La Quinta Inn & Suites by Wyndham Stamford / New York City

La Quinta Inn & Suites by Wyndham Stamford / New York City

3 out of 5
135 Harvard Avenue, Stamford, CT
Fully refundableReserve now, pay when you stay
The price is P5,139 per night from Aug 31 to Sep 1
P5,139
P5,909 total
Aug 31 - Sep 1
includes taxes & fees
6.4/10 (691 reviews)
"Great value with breakfast, staff is very nice and friendly but the room is noisy."

Reviewed on Aug 7, 2025

La Quinta Inn & Suites by Wyndham Stamford / New York City
See all 1,122 properties in New Canaan
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.

Frequently asked questions

How much does a New Canaan vacation package cost?
You can snap up a vacation package to this destination on Expedia. But how much your vacation to New Canaan costs will depend on the length of stay, season and hotel choice.
What are the cheapest months to go to New Canaan?
If you're hoping to book a cheap New Canaan vacation package, consider planning a trip in January, February and March. You'll generally find lower rates on accommodations and flights during these quieter months — ideal for travelers wishing to save money.
How many days is enough for New Canaan?
To get the most out of your New Canaan vacation, we recommend staying for 2 days. Split your time between discovering The Glass House, Silvermine Arts Center and other major sights, in addition to experiencing neighborhoods like North Stamford and Cranbury. If you've got some time to spare, add a tour or day trip to your New Canaan vacation itinerary.
Is it worth booking a vacation package to New Canaan?
Known for its golfing and home to popular attractions like The Glass House, a New Canaan vacation is sure to impress. Another top sight to check out? Don't miss Silvermine Arts Center.
How to find the best New Canaan package deals?
Finding a cheap New Canaan package deal is easy with Expedia. After you've entered your destination and travel dates under our "Packages" tab, set your maximum budget, apply a couple of filters and see what's available. You can tweak your search by "Amenities," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to view the most economical New Canaan package deals. Want a simple trick to get even more savings? Be flexible with your departure dates and consider traveling on a weekday, when prices are generally lower.
Is it cheaper to book a New Canaan vacation as a package?
You can enjoy significant savings on your next New Canaan getaway by booking a personalized vacation package. Click on the "Package" heading, then select your travel dates and destination to view some great flight and hotel prices. Bundling can save travelers hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to New Canaan?
Secure incredible bargains by booking your flights in advance with Expedia. If being spontaneous is more your style, grab one of our last-minute deals for a spur-of-the-moment New Canaan trip.
How to plan a trip to New Canaan?

  1. Pick your dates: What you'd like to do in New Canaan and your favorite season will help you decide when to travel.
  2. Set your budget: Factor in expenses such as flights, food and transportation when calculating how much to put aside for your trip to New Canaan. Then, select a hotel that suits your budget, whether that's a low-cost stay or a deluxe retreat.
  3. Decide how long to go for: Now that you're more familiar with New Canaan, you can figure out the right length of your vacation. Pull together a draft plan and give yourself enough time to cover everything you want to do.
  4. Combine your airfare and accommodations: After you've settled on your dates and duration, book the perfect New Canaan 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.