New Canaan Vacations from $362

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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
per person
Oct 12 - Oct 15
found 18 hours ago
Roundtrip flight included
Los Angeles (LAX) to New York (LGA)
8/10 Very Good! (1,001 reviews)
easy in and easy out, clean and spacious in a great location.

Reviewed on Aug 8, 2025

The Circle Hotel Fairfield

The Circle Hotel Fairfield

3 out of 5
Save 100% on your flight
per person
Sep 18 - Sep 22
found 14 hours ago
Roundtrip flight included
Dallas (DFW) to New York (LGA)
9/10 Wonderful! (1,391 reviews)
Always live staying here:) Something about The Circle that reminds me of when I was growing up:)

Reviewed on Aug 10, 2025

The Sagaponack

The Sagaponack

3 out of 5
Save 100% on your flight
per person
Oct 17 - Oct 20
found 4 hours ago
Roundtrip flight included
Atlanta (ATL) to New York (LGA)
8.8/10 Excellent! (165 reviews)
Great experience. Comfortable beds pool was heated to the perfect temperature. Overall atmosphere is great.

Reviewed on Jul 5, 2025

DUNE Fairfield Beach

DUNE Fairfield Beach

3 out of 5
per person
Oct 12 - Oct 15
found 17 hours ago
Roundtrip flight included
Los Angeles (LAX) to New York (LGA)
9/10 Wonderful! (63 reviews)
Incredible staff, friendly, helpful.

Reviewed on Jun 29, 2025

Wainscott Woods Retreat

Wainscott Woods Retreat

2 out of 5
Save 100% on your flight
per person
Sep 10 - Sep 14
found 23 hours ago
Roundtrip non-stop flight included
Richmond (RIC) to New York (LGA)
10/10 Exceptional! (1 review)
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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

4.5/5(7 reviews)

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

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

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 Sep 1 to Sep 2
$145 total
Sep 1 - Sep 2
Total includes taxes and fees
7.8/10 Good! (1,104 reviews)
"Older fixtures but clean. Sidewalks in parking area in need of repair."

Reviewed on Aug 9, 2025

Hampton Inn White Plains/Tarrytown
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
$148 nightly
The price is $169 total per night from Aug 24 to Aug 25
$169 total
Aug 24 - Aug 25
Total includes taxes and fees
8.2/10 Very Good! (1,395 reviews)
"N/A"

Reviewed on Aug 9, 2025

Baymont by Wyndham White Plains - Elmsford
La Quinta Inn & Suites by Wyndham Stamford / New York City

La Quinta Inn & Suites by Wyndham Stamford / New York City

3 out of 5
135 Harvard Avenue, Stamford, CT
Fully refundableReserve now, pay when you stay
$88 nightly
The price is $102 total per night from Sep 1 to Sep 2
$102 total
Sep 1 - Sep 2
Total includes taxes and fees
6.4/10 (699 reviews)
"Property under renovation. Too many steps to elevator with heavy luggage. 5 steps landing then 5 more steps . Won’t change at hotel. Wouldn’t go back."

Reviewed on Aug 9, 2025

La Quinta Inn & Suites by Wyndham Stamford / New York City
See all 1,126 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.

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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 $362 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.