New Canaan Vacations from $444

Book a Hotel + Flight or Car together to unlock savings

Photo by Marina Timo

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to $1,045 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

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

    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.

The Latest New Canaan vacation packages

Price found within the past 48 hours. Click for updated prices.
Hotel Hi-Ho - Contactless Check-In

Hotel Hi-Ho - Contactless Check-In

3 out of 5
Save 100% on your flight
Price was $614, price is now $444 per person
$444
per person
Oct 9 - Oct 14
found 22 hours ago
Roundtrip flight included
Orlando (MCO) to New York (LGA)
8/10 Very Good! (1,001 reviews)
This property was just fine. We were on the first floor corner, right next to the parking. It was a little loud. The bed comfort was about a 6.5/10. The room was clean, but that cleaning product had a funky smell. Overall, I would probably stay there again if there was no other option.

Reviewed on Aug 18, 2025

The Circle Hotel Fairfield

The Circle Hotel Fairfield

3 out of 5
Save 100% on your flight
Price was $849, price is now $637 per person
$637
per person
Sep 26 - Sep 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (LGA)
9/10 Wonderful! (1,391 reviews)
You should add variety to your breakfasts.

Reviewed on Aug 13, 2025

Don't see what you're looking for?
See all available trips from Columbus to New Canaan
View all trips

Discover the most popular places to visit in New Canaan

Glasshouse by Phillip Johnson, we went there in November and we were able to see it when the Sun is setting. Stunning!!

The Glass House

4.5/5(7 reviews)

You can spend an afternoon studying the exhibits at The Glass House in New Canaan. Check out the lively bars or top-notch restaurants in this family-friendly area.

The Glass House

Waveny Park

4.5/5(5 reviews)

Waveny Park is just one of the places to see in New Canaan, so why not enjoy the other things to explore during your travels? While you're in the area, wander around the parks.

Waveny Park

New Canaan Hotel Deals

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
$127 nightly
The price is $145 total per night from Sep 1 to Sep 2
$145 total
Sep 1 - Sep 2
Total includes taxes and fees
7.8/10 Good! (1,122 reviews)
"Close to 287, mall and dining"

Reviewed on Aug 17, 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
$137 nightly
The price is $157 total per night from Sep 1 to Sep 2
$157 total
Sep 1 - Sep 2
Total includes taxes and fees
8.2/10 Very Good! (1,396 reviews)
"N/A"

Reviewed on Aug 9, 2025

Baymont by Wyndham White Plains - Elmsford
Norwalk Inn & Conference Center

Norwalk Inn & Conference Center

4 out of 5
99 East Avenue, Norwalk, CT
Fully refundableReserve now, pay when you stay
$124 nightly
The price is $143 total per night from Aug 24 to Aug 25
$143 total
Aug 24 - Aug 25
Total includes taxes and fees
8.6/10 Excellent! (1,294 reviews)
"Great value for the money"

Reviewed on Aug 18, 2025

Norwalk Inn & Conference Center
See all 1,124 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.

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 from $444 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.