New Canaan Vacations from $367

Book a Hotel + Flight or Car together to unlock savings

Photo by Marina Timo

  • Plan, book, travel with confidence

  • Better together

    Save up to $1,045 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.

The Latest New Canaan vacation packages

Price found within the past 48 hours. Click for updated prices.
The Circle Hotel Fairfield

The Circle Hotel Fairfield

3 out of 5
Price was $456, price is now $367 per person
$367
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to New York (LGA)
18/10 Exceptional! (1,401 reviews)
The rooms were clean and hotel is quiet . Breakfast was fine and staff was friendly.

Reviewed on Nov 17, 2025

Best Western Plus Fairfield Hotel

Best Western Plus Fairfield Hotel

2.5 out of 5
Price was $1,232, price is now $1,122 per person
$1,122
per person
Dec 27 - Jan 1
found 15 hours ago
Roundtrip flight included
Los Angeles (LAX) to New York (LGA)
16/10 Exceptional! (1,000 reviews)
Very nice clean room and easy parking.

Reviewed on Nov 3, 2025

Hotel Hi-Ho - Contactless Check-In

Hotel Hi-Ho - Contactless Check-In

3 out of 5
Price was $851, price is now $788 per person
$788
per person
Dec 19 - Dec 22
found 14 hours ago
Roundtrip flight included
Los Angeles (QLA) to New York (LGA)
16/10 Exceptional! (1,001 reviews)
It was great for our college visits.

Reviewed on Nov 16, 2025

DUNE Fairfield Beach

DUNE Fairfield Beach

3 out of 5
Price was $864, price is now $790 per person
$790
per person
Dec 30 - Jan 2
found 17 hours ago
Roundtrip flight included
Los Angeles (LAX) to New York (LGA)
18/10 Exceptional! (76 reviews)
Incredible staff, friendly, helpful.

Reviewed on Jun 29, 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 top-notch restaurants or lively bars 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

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
$134 nightly
The price is $154 total per night from Nov 30 to Dec 1
$154 total
Nov 30 - Dec 1
Total with taxes and fees
8.2/10 Very Good! (1,451 reviews)
Baymount Is a one of my go to when i travel

Reviewed on Nov 15, 2025

Baymont by Wyndham White Plains - Elmsford
Sonesta White Plains Downtown

Sonesta White Plains Downtown

4 out of 5
66 Hale Ave White Plains NY
Fully refundableReserve now, pay when you stay
$176 nightly
The price is $201 total per night from Dec 14 to Dec 15
$201 total
Dec 14 - Dec 15
Total with taxes and fees
8.6/10 Excellent! (1,119 reviews)
Lovely property, extremely attentive staff, with a shout out to the gentleman driving the courtesy van! A flawless (albeit too brief) stay.

Reviewed on Nov 12, 2025

Sonesta White Plains Downtown
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 Nov 30 to Dec 1
$145 total
Nov 30 - Dec 1
Total with taxes and fees
7.8/10 Good! (1,276 reviews)
👍

Reviewed on Nov 17, 2025

Hampton Inn White Plains/Tarrytown
See all 1,153 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 from $367 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.