New Canaan Vacations

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $2,000 when you book a flight and hotel together*

  • Find the right fit

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

  • Rest easy

    Plan, book, and manage your trip all in one place

Your New Canaan Vacation

The stress-free way to experience this city is with a customized New Canaan 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 New Canaan includes a little sightseeing, hit up much-loved attractions like The Glass House, Norwalk Maritime Aquarium and The Maritime Aquarium. Expedia is here to help you escape the everyday. Tailor your vacation to New Canaan to match your travel style, whatever that may be.

Stay near popular New Canaan attractions

The Glass House

9.0/10 (8 reviews)
Philip Johnson's modernist masterpiece features walls of glass that dissolve boundaries between inside and nature. Guided tours reveal his visionary design alongside impressive art collections from Stella and Warhol.
See properties

New Canaan Hotel Deals

Tarrytown House Estate

Tarrytown House Estate

3.5 out of 5
49 E Sunnyside Lane Tarrytown NY
Fully refundableReserve now, pay when you stay
$171 nightly
The price is $196 total per night from Aug 2 to Aug 3
$196 total
Aug 2 - Aug 3
Total with taxes and fees
8.2/10 Very Good! (1,183 reviews)
"I couldn’t use the shower gel in shower. So disappointed with that. Breakfast is priced at $30 per person. There is a need to be able to keep up with distance walking and doing stairs. Bring your walking shoes!! The place is huge, multiple wings/buildings you need to use to get around. Outdoor pool ..."

Reviewed on Jul 24, 2026

Tarrytown House Estate
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
$116 nightly
The price is $132 total per night from Aug 2 to Aug 3
$132 total
Aug 2 - Aug 3
Total with taxes and fees
8.4/10 Very Good! (1,766 reviews)
"Good"

Reviewed on Jul 24, 2026

Baymont by Wyndham White Plains - Elmsford
Trumbull Marriott Shelton

Trumbull Marriott Shelton

3.5 out of 5
180 Hawley Ln Trumbull CT
Fully refundableReserve now, pay when you stay
$152 nightly
The price is $175 total per night from Aug 2 to Aug 3
$175 total
Aug 2 - Aug 3
Total with taxes and fees
7.8/10 Good! (1,005 reviews)
"All good! 3 night stay! Comfortable bed and room."

Reviewed on Jul 25, 2026

Trumbull Marriott Shelton
See all 1,191 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.

Find the Best New Canaan Vacation Packages

New Canaan Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Westchester County Airport (HPN)
Population
19,700
Max Temp Winter
35ºF
Max Temp Summer
80ºF
Top Sights
Norwalk Maritime Aquarium, Compo Beach and Ridgefield Playhouse

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

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?
December, January and February are the best times to look for cheap New Canaan vacation packages. Opting to travel in quieter months means you can usually find reduced prices on flights and hotels.
How many days is enough for New Canaan?
When planning your New Canaan vacation, a handful of days will be enough to explore the highlights. Make sure to check out Goldenberry — it's one of the major sights in this destination. If you want more adventure, think about basing yourself here and setting off on some day tours from New Canaan.
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.
Does Expedia offer Book Now, Pay Later New Canaan vacation packages?
Jet off on your ideal getaway to New Canaan with help from Expedia's Book Now, Pay Later vacations. No need to scrimp and save or wait until your next paycheck — we've teamed up with online lender Affirm to give you financial flexibility. Our vacation packages with payment plans allow you to split the cost across 3, 6 or 12 months. With no hidden charges or late payment fees, it's a breeze to budget for your trip and snap up bargains while they last.

Explore a world of travel with Expedia

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