New Canaan Vacations

Book a Hotel + Flight together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to SARĀ 5,400 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

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 SARĀ 581 per night from Aug 2 to Aug 3
SARĀ 581
SARĀ 801 total
2 Aug - 3 Aug
includes taxes & fees
8.2/10 Very Good! (1,163 reviews)
"This hotel was great for what I was looking for for the weekend. It's very family friendly, even dogs are allowed! The room was just fine but it did have a bit of a damp smell and it was very dark. My room was at the basement level so I would ask about getting an above ground room next time. The ..."

Reviewed on 18 July 2026

Tarrytown House Estate
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
The price is SARĀ 656 per night from Aug 17 to Aug 18
SARĀ 656
SARĀ 875 total
17 Aug - 18 Aug
includes taxes & fees
8.8/10 Excellent! (1,323 reviews)
"x"

Reviewed on 17 July 2026

Sonesta White Plains Downtown
Hyatt Regency Greenwich

Hyatt Regency Greenwich

4 out of 5
1800 E Putnam Avenue Old Greenwich CT
Fully refundableReserve now, pay when you stay
The price is SARĀ 785 per night from Jul 26 to Jul 27
SARĀ 785
SARĀ 903 total
26 Jul - 27 Jul
includes taxes & fees
8.6/10 Excellent! (1,072 reviews)
"Q"

Reviewed on 18 July 2026

Hyatt Regency Greenwich
See all 1,190 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?
Offering great value package deals on Expedia, you'll be thrilled with how little a vacation to New Canaan costs! Our packages mean less travel planning for you and greater savings.
What are the cheapest months to go to New Canaan?
January, February and March are the best times to look for cheap New Canaan vacation packages. Opting to travel in less busy periods means you can usually find better prices on flights and accommodations.
How to find the best New Canaan package deals?
Use Expedia's handy filters to help you find some terrific New Canaan package deals. When you start your search, simply set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your adventure for midweek, or browse for New Canaan package deals in the off-peak season. Play around with your travel dates and you may score even bigger discounts. As a rule of thumb, it's typically best to lock in your vacation package as soon as possible.
Is it cheaper to book a New Canaan vacation as a package?
You can enjoy significant savings on your next New Canaan retreat by booking a personalized vacation package. Check the "Package" heading, then enter your destination and travel dates to see the best airfares and hotel prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to New Canaan?
If you're considering an impromptu New Canaan getaway, browse our last-minute deals that can be booked up to one week before you take off. Prefer not to wait until the last minute? You can land awesome deals on your flights and hotels by booking ahead.
How to plan a trip to New Canaan?

  1. Choose your dates: What you plan to do in New Canaan and your preferred season can help you decide when to travel.
  2. Plan your budget wisely: On top of the cost of your accommodations, you should factor in other expenses too. These include food, transportation and flights. Also, set aside a little extra for unexpected costs that may arise during your trip to New Canaan.
  3. Decide how many days away: Start by compiling a list of the attractions you want to get to in New Canaan. Then, estimate how long you'll need at each, as well as any travel time.
  4. Combine your accommodations and airfare: Once you've settled on your travel dates and duration, book the perfect New Canaan vacation package for you.