New Canaan Vacations

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Find the Best New Canaan Vacation Packages

New Canaan Hotel Deals

Tarrytown House Estate

Tarrytown House Estate

3.5 out of 5
49 E Sunnyside Lane Tarrytown NY
Fully refundableReserve now, pay when you stay
The price is ￥31,512 per night from Nov 19 to Nov 20
￥31,512
￥40,000 total
Nov 19 - Nov 20
includes taxes & fees
Tarrytown House Estate
East Norwich Inn

East Norwich Inn

2.5 out of 5
6321 Northern Blvd. East Norwich NY
The price is ￥19,287 per night from Nov 19 to Nov 20
￥19,287
￥22,176 total
Nov 19 - Nov 20
includes taxes & fees
8/10 Very Good! (1,808 reviews)
"I was looking for a place to stay for the night after a long day and did not want to drive home with all the late afternoon traffic and saw this hotel online. It met all my needs. it was clean, quiet and the personnel were friendly. Thank you"

Reviewed on Nov 4, 2026

East Norwich Inn
J House Greenwich

J House Greenwich

4 out of 5
1114 E. Putnam Ave Riverside CT
The price is ￥44,076 per night from Nov 20 to Nov 21
￥44,076
￥57,249 total
Nov 20 - Nov 21
includes taxes & fees
J House Greenwich
See all 1,200 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.

Stay near popular New Canaan attractions

The Glass House

9.0/10 (8 reviews)
Philip Johnson's modernist masterpiece features walls of glass that dissolve boundaries between inside and nature. Guided tours reveal his visionary design alongside impressive art collections from Stella and Warhol.
See properties

Frequently asked questions

How much does a New Canaan vacation package cost?
You can snap up a vacation package to this destination 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?
If you're hoping to book a cheap New Canaan vacation package, consider planning a trip in January, February and March. You'll generally find lower rates on accommodations and flights during these quieter months — ideal for travelers wishing to save money.
How many days is enough for New Canaan?
To get the most out of your New Canaan vacation, we recommend staying for 2 days. Split your time between discovering The Glass House, Silvermine Arts Center and other major sights, in addition to experiencing neighborhoods like North Stamford and Cranbury. If you've got some time to spare, add a tour or day trip to your New Canaan vacation itinerary.
Is it worth booking a vacation package to New Canaan?
Known for its golfing and home to popular attractions like The Glass House, a New Canaan vacation is sure to impress. Another top sight to check out? Don't miss Silvermine Arts Center.
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.
How to plan a trip to New Canaan?

  1. Pick your dates: What you'd like to do in New Canaan and your favorite season will help you decide when to travel.
  2. Set your budget: Factor in expenses such as flights, food and transportation when calculating how much to put aside for your trip to New Canaan. Then, select a hotel that suits your budget, whether that's a low-cost stay or a deluxe retreat.
  3. Decide how long to go for: Now that you're more familiar with New Canaan, you can figure out the right length of your vacation. Pull together a draft plan and give yourself enough time to cover everything you want to do.
  4. Combine your airfare and accommodations: After you've settled on your dates and duration, book the perfect New Canaan vacation package for you.

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