New Canaan Vacations from $340

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
Grasmere
Save 100% on your flight
Price was $459, price is now $340 per person
$340
per person
Mar 21 - Mar 25
found 1 day ago
Roundtrip flight included
Chicago (ORD) to New York (LGA)
9/10 Wonderful! (1,401 reviews)
The room was clean. It’s very close to the main road and got noisy but overall it was fine.

Reviewed on Feb 9, 2026

Windrose On Hudson

Windrose On Hudson

3 out of 5
Price was $627, price is now $451 per person
$451
per person
Apr 17 - Apr 20
found 7 hours ago
Roundtrip flight included
West Palm Beach (PBI) to New York (LGA)
7.8/10 Good! (80 reviews)
The rooms need more amenities such as a coffee maker some cups and utensils, as well as a guide to the television set.

Reviewed on Dec 28, 2025

Hotel Hi-Ho - Contactless Check-In

Hotel Hi-Ho - Contactless Check-In

3 out of 5
Greenfield Hill
Price was $431, price is now $347 per person
$347
per person
Apr 17 - Apr 20
found 8 hours ago
Roundtrip flight included
West Palm Beach (PBI) to New York (LGA)
8/10 Very Good! (1,001 reviews)
Easy check. Great location, right off of the high way and close to SHU.

Reviewed on Feb 11, 2026

Best Western Plus Fairfield Hotel

Best Western Plus Fairfield Hotel

2.5 out of 5
Grasmere
Price was $500, price is now $414 per person
$414
per person
Apr 17 - Apr 20
found 8 hours ago
Roundtrip flight included
West Palm Beach (PBI) to New York (LGA)
8/10 Very Good! (1,000 reviews)
The room was very clean and the staff was very responsive and kind.

Reviewed on Feb 6, 2026

DUNE Fairfield Beach

DUNE Fairfield Beach

3 out of 5
Fairfield Beach
Price was $651, price is now $556 per person
$556
per person
Apr 17 - Apr 20
found 8 hours ago
Roundtrip flight included
West Palm Beach (PBI) to New York (LGA)
9/10 Wonderful! (76 reviews)
The room was spotless and cozy and the location couldn't be better!

Reviewed on Nov 30, 2025

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

The Annual Vacation Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.
Book now

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

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

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
$122 nightly
The price is $140 total per night from Feb 22 to Feb 23
$140 total
Feb 22 - Feb 23
Total with taxes and fees
8.2/10 Very Good! (1,543 reviews)
Yes the room was spotless and the staff were all very welcoming

Reviewed on Feb 12, 2026

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
$189 nightly
The price is $216 total per night from Mar 9 to Mar 10
$216 total
Mar 9 - Mar 10
Total with taxes and fees
8.8/10 Excellent! (1,283 reviews)
Lovely space and kind staff. Breakfast was delicious.

Reviewed on Feb 11, 2026

Sonesta White Plains Downtown
EVEN Hotel Norwalk by IHG

EVEN Hotel Norwalk by IHG

3.5 out of 5
426 Main Ave, Route 7 Norwalk CT
Fully refundable
$131 nightly
The price is $151 total per night from Mar 15 to Mar 16
$151 total
Mar 15 - Mar 16
Total with taxes and fees
8.4/10 Very Good! (1,078 reviews)
Bad weather the might we stayed. Parking lot was an ice rink all morning long. No one came out to put salt down until 10am. Booked through Hotels.com but hotel charged us an ADDITIONAL $300. Just a nightmare and unprofessional staff. Do not stay here.

Reviewed on Feb 11, 2026

EVEN Hotel Norwalk by IHG
See all 1,197 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 $340 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.