New Canaan Vacations
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ￥109,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Find the Best New Canaan Vacation Packages
New Canaan Hotel Deals
Tarrytown House Estate
49 E Sunnyside Lane Tarrytown NY
Fully refundableReserve now, pay when you stay
￥25,084
￥32,634 total
Aug 30 - Aug 31
includes taxes & fees
8.2/10 Very Good! (1,237 reviews)
"We had another great staycation! Staff was amazing especially the great people at the front desk! Pool and grounds were so nice to enjoy the summer days and nights! We’ll definitely be coming back!"
Reviewed on Aug 11, 2026
Sonesta White Plains Downtown
66 Hale Ave White Plains NY
Fully refundableReserve now, pay when you stay
￥26,228
￥35,233 total
Sep 6 - Sep 7
includes taxes & fees
8.8/10 Excellent! (1,350 reviews)
"Entire facility was amazing. Property was well maintained and very well appointed. Room was clean and spacious. Always ample parking for hotel guests. Would recommend staying to all"
Reviewed on Aug 11, 2026
Hyatt Regency Greenwich
1800 E Putnam Avenue Old Greenwich CT
Fully refundableReserve now, pay when you stay
￥28,026
￥32,230 total
Sep 6 - Sep 7
includes taxes & fees
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.
New Canaan Library
New Canaan Library serves as a vibrant hub for learning and community engagement. Explore their diverse collection, attend cultural events, or utilize their specialized spaces for children and teens.
Waveny Park
9.0/10 (6 reviews)
Roam the 250-acre Waveny Park with its historic Tudor mansion and miles of woodland trails. The formal gardens and sprawling meadows offer a serene backdrop for picnics among picturesque surroundings.
Silvermine Arts Center
This historic arts center has nurtured creativity since 1922 in its serene Silvermine neighborhood setting. Explore five diverse galleries or join classes across various mediums for an immersive artistic experience.
New Canaan Historical Society
This historical society showcases New Canaan's colonial past and mid-century modern heritage through the 1764 Hanford-Silliman House and 1960 Gores Pavilion, offering a journey through Connecticut's design evolution.
Old Stamford Road Bird Sanctuary
You can take time to visit Old Stamford Road Bird Sanctuary during your travels to New Canaan. Discover the coral reefs while you're in the area.
Browning Wildlife Sanctuary
This 10-acre woodland sanctuary offers serene trails with views of Grupes Reservoir and educational signs. Enjoy the tranquil 0.7-mile path through quiet forest, perfect for nature enthusiasts.
New Canaan Nature Center
This 40-acre sanctuary showcases diverse habitats from butterfly gardens to wooded trails. Observe live animal ambassadors including owls and falcons while exploring the center's interactive environmental exhibits.
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?
- Pick your dates: What you'd like to do in New Canaan and your favorite season will help you decide when to travel.
- 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.
- 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.
- 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.
