New Canaan Vacation Packages

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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.

Top New Canaan Vacation Deals

Price found within the past 48 hours. Click for updated prices.
The Sagaponack

The Sagaponack

3 out of 5
Price was CA $1,410, price is now CA $1,295 per person
CA $1,295
per person
Oct 9 - Oct 12
found 22 hours ago
Roundtrip flight included
Detroit (DTW) to New York (LGA)
8.8/10 Excellent! (170 reviews)
Great experience. Comfortable beds pool was heated to the perfect temperature. Overall atmosphere is great.

Reviewed on Jul. 5, 2025

Wainscott Woods Retreat

Wainscott Woods Retreat

2 out of 5
Price was CA $5,292, price is now CA $4,815 per person
CA $4,815
per person
Sep 24 - Sep 28
found 6 hours ago
Roundtrip non-stop flight included
Halifax (YHZ) to New York (LGA)
10/10 Exceptional! (1 review)
HIDDEN GEM IN THE HEART OF HAMPTONS! What a special place to stay in the Hamptons! I am so happy we found this wonderful gem! This hotel is clean, quiet and well managed. The pool is beautiful the rooms are modern, sleek and clean! The grounds are beautifully manicured. The location is perfect! This new hotel has the charm of a bed and breakfast. The hotel is a short car ride from either East Hampton or Southampton which is perfect if you chose to explore all the little towns the Hampton's has to offer. Wainscott Retreat is the perfect place to visit if you want to get away with your family, girlfriends or as a couple! You will NOT regret staying at this hotel! I cannot wait to return !

Reviewed on Jul. 17, 2025

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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
The price is CA $176 per night from Sep 1 to Sep 2
CA $176
CA $201 total
Sep 1 - Sep 2
includes taxes & fees
7.8/10 Good! (1,128 reviews)
Good hotel but rude guests
"The staff were very nice and helpful. The room could do with a refresh but was clean and comfortable. The noise from the roads outside was loud making sleep harder. The dog barking on one side and the constant arguing on the other side didn't help. More soundproofing would be nice. Breakfast and ..."

Reviewed on Aug. 22, 2025

Hampton Inn White Plains/Tarrytown
Amsterdam Hotel

Amsterdam Hotel

2 out of 5
19 Clarks Hill Ave, Stamford, CT
Fully refundableReserve now, pay when you stay
The price is CA $116 per night from Sep 8 to Sep 9
CA $116
CA $134 total
Sep 8 - Sep 9
includes taxes & fees
8.4/10 Very Good! (1,637 reviews)
"Good deal for the price. Room clean, staff always pleasant, professional and helpful"

Reviewed on Aug. 19, 2025

Amsterdam Hotel
Norwalk Inn & Conference Center

Norwalk Inn & Conference Center

4 out of 5
99 East Avenue, Norwalk, CT
Fully refundableReserve now, pay when you stay
The price is CA $161 per night from Aug 24 to Aug 25
CA $161
CA $186 total
Aug 24 - Aug 25
includes taxes & fees
8.6/10 Excellent! (1,283 reviews)
"This hotel has great food, drink and meeting spaces My room was extremely comfortable and clean. Would highly recommend for business and leisure activities A+"

Reviewed on Aug. 21, 2025

Norwalk Inn & Conference Center
See all 1,121 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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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 lively bars or top-notch restaurants in this family-friendly area.

The Glass House

Frequently asked questions

How much does a New Canaan vacation package cost?
Offering great value package deals from CA $1,295 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 many days is enough for New Canaan?
To fully enjoy a New Canaan vacation, we suggest booking for 2 days. Divide your time between discovering The Maritime Aquarium, The SoNo Collection and other must-see attractions, as well as experiencing neighbourhoods like North Stamford and Cranbury. If you've got some time to spare, add a day trip to your New Canaan vacation itinerary.
Is it worth booking a vacation package to New Canaan?
Boasting a host of highlights starting with its top-notch golfing, New Canaan is a good vacation destination. Whether you'd like to discover sights like The Glass House and Silvermine Arts Centre or venture off the beaten track, you'll find plenty to keep you busy during your New Canaan vacation.
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.

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