New Canaan Vacations from $395
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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.
The Latest New Canaan Vacation Packages
- Newark Hansbury Multi Level House
Jan 20 - Jan 24Newark Hansbury Multi Level House + Flight
Weequahic4 nights2.0 star property6.8/10 - (5 reviews)"nice"Reviewed September 10, 2026Roundtrip • Atlanta (ATL) - New York (JFK)ATL - EWR • Nonstop LGA - ATL • Nonstop$665$395found 1 day agoper traveler - JW Marriott Essex House New York
Jan 21 - Jan 25JW Marriott Essex House New York + Flight
Manhattan4 nights4.5 star property8.8/10 - Excellent (1,000 reviews)Roundtrip • Atlanta (ATL) - New York (JFK)ATL - JFK • Nonstop JFK - ATL • Nonstop$1,678$945found 1 day agoper traveler - 1 Hotel Brooklyn Bridge
Jan 11 - Jan 151 Hotel Brooklyn Bridge + Flight
Brooklyn4 nights5.0 star property9.2/10 - Wonderful (1,001 reviews)Roundtrip • Dallas (DFW) - New York (JFK)DFW - LGA • Nonstop LGA - DFW • Nonstop - INNSiDE by Meliá New York Nomad
Jan 7 - Jan 11INNSiDE by Meliá New York Nomad + Flight
Manhattan4 nights4.5 star property9.2/10 - Wonderful (2,370 reviews)"The hotel was nice but upon check out, we were incorrectly charged a $435 smoking fee. I called to have the charge removed and they said they had to get a third party involved"Reviewed November 6, 2026Roundtrip • Atlanta (ATL) - New York (JFK)ATL - JFK • Nonstop JFK - ATL • Nonstop$1,083$631found 1 day agoper traveler - Hotel Riu Plaza New York Times Square
Jan 14 - Jan 17Hotel Riu Plaza New York Times Square + Flight
Manhattan3 nights4.0 star property9.0/10 - Wonderful (3,455 reviews)"The room was clean and ready each night. The breakfast was beyond belief and the staff were helpful and professional. The location was walking distant from Broadway and great restaurants."Reviewed November 6, 2026Roundtrip • Atlanta (ATL) - New York (JFK)ATL - LGA • Nonstop LGA - ATL • Nonstop
Where to stay near New Canaan
Stamford
Discover Stamford, a vibrant city ideal for travelers seeking a dynamic mix of urban and outdoor experiences. With attractions like Greenwich Avenue for shopping, The Glass House museum for art enthusiasts, and the historic charm of South Norwalk, Stamford offers a rich palette of activities. Located about 7 miles by car from New Canaan, it serves as a convenient base for exploring the area. With its diverse offerings, Stamford is a smart choice for your next hotel booking.
Norwalk
Experience the charm of Norwalk, an excellent hub for travelers seeking a mix of city excitement and outdoor adventures. With attractions like the historic South Norwalk, the modern Fairfield University, and the beautiful Compo Beach, visitors can enjoy a vibrant getaway year-round. Located about 5 miles by car from New Canaan, Norwalk offers convenient access to shopping, education, and family-friendly activities. Choosing Norwalk for your stay ensures a delightful blend of experiences just moments away.
Westport
If you are a traveler seeking a weekend getaway, look no further than Westport, which features beautiful beaches and scenic outdoor areas perfect for relaxation. With attractions like Compo Beach for sunbathing, Fairfield University for a dose of culture, and Historic South Norwalk for history buffs, Westport promises a delightful experience. Located about 7 miles by car from New Canaan, it’s an ideal choice for a charming stay that balances leisure and adventure.
Darien
Ideal for family vacationers and weekend getaway seekers, Darien stands out as a prime spot for travelers interested in outdoor and city experiences. Here, you can explore local attractions like the scenic beach and lake, or enjoy shopping along Greenwich Avenue. Additionally, the historic charm of South Norwalk and the artistic allure of The Glass House offer enriching experiences. Located about 5 miles from New Canaan, Darien is a smart choice for your next hotel booking, providing a perfect blend of relaxation and adventure.
Wilton
Travelers visiting the area often choose Wilton, especially those seeking a family-friendly getaway or a romantic escape. This charming city offers access to beautiful outdoor spaces, such as lakes and parks, as well as attractions like the modern Fairfield University and the intriguing Glass House museum. With its close proximity to New Canaan, about 4 miles away, Wilton serves as a smart choice for a relaxing stay, blending convenience with a delightful local experience.
Discover the most popular places to visit in New Canaan
New Canaan Hotel Deals
"Excellent"
"Room was so clean and bed was fabulous!! Staff is y friendly and the complimentary breakfast was outstanding!!"
"I had a nice and comfortable stay. The staff were very welcoming and the location seemed very neat. I was not able to use the amenities due to my short stay but I’m sure it’s not far from being well kept. The location is great for local things to be done"
"What I loved : extremely clean both in the room and the common areas , very nice and helpful staff, quiet atmosphere, comfy beds , safe parking . What was disappointing : the plumbing needs more consistent maintenance , last trip we had only hot water in the shower and had to switch rooms , this trip the bathroom sink drain had to be cleaned during our stay , and the lobby bathroom failed to flush . Also, the electric needs maintenance - three plugs did not work in my room , so I was drying my...
The Armon Stamford Hotel & Conference
The Armon Stamford Hotel & Conference
Residence Inn by Marriott Norwalk
Residence Inn by Marriott Norwalk
Extended Stay America Suites Norwalk Stamford
Extended Stay America Suites Norwalk Stamford"room fine kitchen completey empty"
Frequently Asked Questions
How much does a New Canaan vacation package cost?
You can snap up a vacation package to this destination from $395 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?
December, January and February are the best times to look for cheap New Canaan vacation packages. Opting to travel in quieter months means you can usually find reduced prices on flights and hotels.
How many days is enough for New Canaan?
When planning your New Canaan vacation, a handful of days will be enough to explore the highlights. Make sure to check out Goldenberry — it's one of the major sights in this destination. If you want more adventure, think about basing yourself here and setting off on some day tours from New Canaan.
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.
Does Expedia offer Book Now, Pay Later New Canaan vacation packages?
Jet off on your ideal getaway to New Canaan with help from Expedia's Book Now, Pay Later vacations. No need to scrimp and save or wait until your next paycheck — we've teamed up with online lender Affirm to give you financial flexibility. Our vacation packages with payment plans allow you to split the cost across 3, 6 or 12 months. With no hidden charges or late payment fees, it's a breeze to budget for your trip and snap up bargains while they last.