New Canaan Holidays

Book a Hotel + Flight or Car together to unlock savings

Top hotels in New Canaan

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 4.884.360 ₫ per night from 16 Jul to 17 Jul
4.884.360 ₫
6.457.530 ₫ total
16 Jul - 17 Jul
includes taxes & fees
8.8/10 Excellent! (1,333 reviews)
"Overall great stay. Food, bar, staff, room all nice"

Reviewed on 13 Jul 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 5.567.120 ₫ per night from 2 Aug to 3 Aug
5.567.120 ₫
6.402.188 ₫ total
2 Aug - 3 Aug
includes taxes & fees
Hyatt Regency Greenwich
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 4.060.321 ₫ per night from 2 Aug to 3 Aug
4.060.321 ₫
5.600.733 ₫ total
2 Aug - 3 Aug
includes taxes & fees
8.2/10 Very good! (1,173 reviews)
"Room was very clean. Refrigerator was noisy. Price was great."

Reviewed on 13 Jul 2026

Tarrytown House Estate
See all 1,180 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 holiday package cost?
You can snap up a holiday package to this destination on Expedia. But how much your holiday 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 holiday package, consider planning a trip in January, February and March. You'll generally find lower rates on accommodation and flights during these quieter months — ideal for travellers wishing to save money.
How many days is enough for New Canaan?
To get the most out of your New Canaan holiday, we recommend staying for 2 days. Split your time between discovering The Glass House, Silvermine Arts Centre and other major sights, in addition to experiencing neighbourhoods like North Stamford and Cranbury. If you've got some time to spare, add a tour or day trip to your New Canaan holiday itinerary.
Is it worth booking a holiday package to New Canaan?
Known for its golfing and home to popular attractions like The Glass House, a New Canaan holiday is sure to impress. Another top sight to check out? Don't miss Silvermine Arts Centre.
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 travelling on a weekday, when prices are generally lower.
Is it cheaper to book a New Canaan holiday as a package?
You can enjoy significant savings on your next New Canaan getaway by booking a personalised holiday package. Click on the "Package" heading, then select your travel dates and destination to view some great flight and hotel prices. Bundling can save travellers hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a holiday 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 favourite 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 holiday. Pull together a draft plan and give yourself enough time to cover everything you want to do.
  4. Combine your airfare and accommodation: After you've settled on your dates and duration, book the perfect New Canaan holiday package for you.

Explore a world of travel with Expedia