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 AEDĀ 689 per night from Nov 15 to Nov 16
AEDĀ 689
AEDĀ 879 total
15 Nov - 16 Nov
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 AEDĀ 434 per night from Nov 30 to Dec 1
AEDĀ 434
AEDĀ 499 total
30 Nov - 1 Dec
includes taxes & fees
8/10 Very Good! (1,805 reviews)
"Our check in began with an indifferent, abrupt front desk person. We had booked last minute, so we got whatever room was available. You canā€™t predict who your neighbors will be, but ours were noisy and the smell of pot permeated our room and followed us out on our clothes the next morning. We were ..."

Reviewed on 11 November 2026

East Norwich Inn
Sleepy Hollow Hotel, a Dolce by Wyndham

Sleepy Hollow Hotel, a Dolce by Wyndham

3.5 out of 5
455 S Broadway Tarrytown NY
Fully refundableReserve now, pay when you stay
The price is AEDĀ 487 per night from Dec 8 to Dec 9
AEDĀ 487
AEDĀ 558 total
8 Dec - 9 Dec
includes taxes & fees
Sleepy Hollow Hotel, a Dolce by Wyndham
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.

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.