New Canaan Vacations from $429

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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 Sagaponack

The Sagaponack

3 out of 5
Price was $485, price is now $429 per person
$429
per person
Mar 21 - Mar 24
found 1 day ago
Roundtrip flight included
Miami (MIA) to New York (LGA)
8.8/10 Excellent! (205 reviews)
The property and room was clean, easily accessible, and staff were very friendly. We would stay here again!

Reviewed on Jan 3, 2026

Windrose On Hudson

Windrose On Hudson

3 out of 5
Price was $1,324, price is now $876 per person
$876
per person
Mar 28 - Apr 3
found 1 day ago
Roundtrip non-stop flight included
Burbank (BUR) 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 $475, price is now $430 per person
$430
per person
Mar 6 - Mar 8
just found
Roundtrip non-stop flight included
Burbank (BUR) to New York (LGA)
8/10 Very Good! (1,001 reviews)
The room was clean and comfortable. There is no refridgerator

Reviewed on Jan 20, 2026

Wainscott Woods Retreat

Wainscott Woods Retreat

2.5 out of 5
Price was $692, price is now $647 per person
$647
per person
Mar 21 - Mar 24
found 1 day ago
Roundtrip flight included
Miami (MIA) to New York (LGA)
7/10 Good! (9 reviews)
Newly Renovated and extremely clean, well kept, and inviting rooms. Staff could not be nicer and more accommodating. Location is ideally situated close to lots of shops, Goldbergs for bagels, East Hampton Beaches etc. Highly recommend this accommodation to anyone staying in the area.

Reviewed on Oct 15, 2025

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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

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
$180 nightly
The price is $206 total per night from Feb 14 to Feb 15
$206 total
Feb 14 - Feb 15
Total with taxes and fees
8.6/10 Excellent! (1,227 reviews)
Excellent

Reviewed on Jan 18, 2026

Sonesta White Plains Downtown
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 $139 total per night from Jan 29 to Jan 30
$139 total
Jan 29 - Jan 30
Total with taxes and fees
8.2/10 Very Good! (1,501 reviews)
The stay was great but I picked a night when there was a huge party going on. The guys in the room next door were partying till past 5.30am. If not for that my score for comfort would be better

Reviewed on Jan 18, 2026

Baymont by Wyndham White Plains - Elmsford
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
$122 nightly
The price is $140 total per night from Jan 29 to Jan 30
$140 total
Jan 29 - Jan 30
Total with taxes and fees
7.8/10 Good! (1,345 reviews)
Clean nice staff

Reviewed on Jan 17, 2026

Hampton Inn White Plains/Tarrytown
See all 1,180 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

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Frequently asked questions

How much does a New Canaan vacation package cost?
You can snap up a vacation package to this destination from $429 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.

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