New Canaan Vacations from $458

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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.
Hotel Hi-Ho - Contactless Check-In

Hotel Hi-Ho - Contactless Check-In

3 out of 5
Greenfield Hill
Price was $585, price is now $458 per person
$458
per person
May 21 - May 25
found 22 hours ago
Roundtrip flight included
West Palm Beach (PBI) to New York (LGA)
8/10 Very Good! (1,005 reviews)
Walls were dirty, room smelled damp, no parking when we arrived, parking lot was completely full .. restaurant on site had so many lingering people smoking around smoking cigarettes I was a little surprised by condition of room pictures look better then actual person

Reviewed on Mar 22, 2026

Cozy Cottage with Fire Pit

Cozy Cottage with Fire Pit

2 out of 5
Save 100% on your flight
Price was $1,669, price is now $1,166 per person
$1,166
per person
May 21 - May 25
found 22 hours ago
Roundtrip flight included
West Palm Beach (PBI) to New York (LGA)
No reviews
Windrose On Hudson

Windrose On Hudson

3 out of 5
Price was $729, price is now $543 per person
$543
per person
May 21 - May 24
found 1 day ago
Roundtrip flight included
West Palm Beach (PBI) to New York (LGA)
8.4/10 Very Good! (116 reviews)
Room was clean, super quiet, staff was very helpful and nice

Reviewed on Feb 15, 2026

The Circle Hotel Fairfield

The Circle Hotel Fairfield

3 out of 5
Grasmere
Price was $644, price is now $493 per person
$493
per person
Jun 26 - Jun 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (LGA)
9/10 Wonderful! (1,431 reviews)
We very much enjoyed our stay at the Circle Hotel. The staff were pleasant and helpful and the bed was very comfortable. I will be going back there again.

Reviewed on Mar 30, 2026

The Sagaponack

The Sagaponack

3 out of 5
Price was $810, price is now $686 per person
$686
per person
May 13 - May 16
found 20 hours ago
Roundtrip flight included
Tampa (TPA) to New York (LGA)
8.8/10 Excellent! (228 reviews)
Wonderful! What a beautiful property, room and the location is perfection!

Reviewed on Mar 29, 2026

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Discover the most popular places to visit in New Canaan

The Glass House

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
$123 nightly
The price is $141 total per night from Apr 12 to Apr 13
$141 total
Apr 12 - Apr 13
Total with taxes and fees
8.2/10 Very Good! (1,626 reviews)
It wasn't that bad. I gave 4 stars because I found fake eyelashes in my bathroom. Plus the pool was warm but the pool area was super cold. Everyone was sitting with either a sweater or towel wrapped around them. Breakfast was great. Staff was pleasant. I would go back.

Reviewed on Mar 29, 2026

Baymont by Wyndham White Plains - Elmsford
East Norwich Inn

East Norwich Inn

2.5 out of 5
6321 Northern Blvd. East Norwich NY
$128 nightly
The price is $143 total per night from Apr 1 to Apr 2
$143 total
Apr 1 - Apr 2
Total with taxes and fees
8/10 Very Good! (1,823 reviews)
The entry key card didn't work very well and the night clerk was condescending when I told him about it. He just ran it through the card machine, which didn't help.

Reviewed on Mar 28, 2026

East Norwich Inn
Tarrytown House Estate

Tarrytown House Estate

3.5 out of 5
49 E Sunnyside Lane Tarrytown NY
Fully refundableReserve now, pay when you stay
$168 nightly
The price is $192 total per night from Apr 1 to Apr 2
$192 total
Apr 1 - Apr 2
Total with taxes and fees
8.2/10 Very Good! (1,043 reviews)
My car with handicap tag was safe in front of office.but my husband and I are unable to walk the length to our room without knee,ankle and back pain acting up.We had to make the walk several times to get our food.Could have used a closer room ours was a block or two away.

Reviewed on Mar 31, 2026

Tarrytown House Estate
See all 1,201 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 $458 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.