New Canaan Vacations from $275

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Photo by Marina Timo

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
Price was $344, price is now $275 per person
$275
per person
Jan 16 - Jan 19
found 14 hours ago
Roundtrip flight included
Raleigh (RDU) to New York (LGA)
8/10 Very Good! (1,001 reviews)
Clean as a whistle. Friendly staff

Reviewed on Dec 5, 2025

The Circle Hotel Fairfield

The Circle Hotel Fairfield

3 out of 5
Save 100% on your flight
Price was $752, price is now $530 per person
$530
per person
Jan 16 - Jan 23
found 7 hours ago
Roundtrip flight included
Orlando (MCO) to New York (LGA)
9/10 Wonderful! (1,401 reviews)
Clean, updated room, easy check in & out. Staff was very nice

Reviewed on Dec 6, 2025

Stareway to Heaven in Fairfield

Stareway to Heaven in Fairfield

2 out of 5
Save 100% on your flight
Price was $1,964, price is now $1,570 per person
$1,570
per person
Jan 16 - Jan 23
found 7 hours ago
Roundtrip flight included
Orlando (MCO) to New York (LGA)
No reviews
DUNE Fairfield Beach

DUNE Fairfield Beach

3 out of 5
Save 100% on your flight
Price was $924, price is now $761 per person
$761
per person
Jan 16 - Jan 23
found 7 hours ago
Roundtrip flight included
Orlando (MCO) 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

Best Western Plus Fairfield Hotel

Best Western Plus Fairfield Hotel

2.5 out of 5
Price was $655, price is now $600 per person
$600
per person
Jan 16 - Jan 23
found 7 hours ago
Roundtrip flight included
Orlando (MCO) to New York (LGA)
8/10 Very Good! (1,000 reviews)
Such a nice little place

Reviewed on Nov 24, 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 top-notch restaurants or lively bars 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
$125 nightly
The price is $143 total per night from Jan 4 to Jan 5
$143 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
8.2/10 Very Good! (1,475 reviews)
Comfortable and clean. In a good location off the highway and near the bridge. Great price for location!

Reviewed on Dec 1, 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
$178 nightly
The price is $203 total per night from Jan 4 to Jan 5
$203 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
8.6/10 Excellent! (1,152 reviews)
Great stay

Reviewed on Dec 1, 2025

Sonesta White Plains Downtown
Tarrytown House Estate

Tarrytown House Estate

3.5 out of 5
49 E Sunnyside Lane Tarrytown NY
Fully refundableReserve now, pay when you stay
$179 nightly
The price is $205 total per night from Dec 21 to Dec 22
$205 total
Dec 21 - Dec 22
Total with taxes and fees
8/10 Very Good! (1,025 reviews)
The staff were really friendly, and the property was extremely beautiful!

Reviewed on Nov 30, 2025

Tarrytown House Estate
See all 1,157 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 $275 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.