New Canaan Vacations from US$ 299
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Photo by Marina Timo
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
Price found within the past 48 hours. Click for updated prices.
Hotel Hi-Ho - Contactless Check-In
Greenfield Hill
Price was US$ 374, price is now US$ 299 per person
US$ 299
per person
Apr 3 - Apr 6
found 1 day ago
Roundtrip flight included
Raleigh (RDU) to New York (LGA)
8/10 Very Good! (1,001 reviews)
Extremely clean room, quiet and comfortable, great heating/ac unit and a liquor store literally right next door! Couldn’t ask for a better, more affordable hotel. Loved it.
Reviewed on 25 Jan, 2026
Windrose On Hudson
Save 100% on your flight
Price was US$ 1,006, price is now US$ 657 per person
US$ 657
per person
Mar 12 - Mar 18
found 16 hours ago
Roundtrip flight included
Atlanta (ATL) to New York (LGA)
7.8/10 Good! (80 reviews)
The rooms need more amenities such as a coffee maker some cups and utensils, as well as a guide to the television set.
Reviewed on 28 Dec, 2025
The Circle Hotel Fairfield
Grasmere
Price was US$ 420, price is now US$ 346 per person
US$ 346
per person
Apr 6 - Apr 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (LGA)
9/10 Wonderful! (1,401 reviews)
Room was great! The bed and couch was amazing! Coming again soon
Reviewed on 18 Jan, 2026
The Sagaponack
Price was US$ 597, price is now US$ 521 per person
US$ 521
per person
Mar 19 - Mar 23
found 8 hours ago
Roundtrip flight included
Atlanta (ATL) to New York (LGA)
8.8/10 Excellent! (205 reviews)
The property and room was clean, easily accessible, and staff were very friendly. We would stay here again!
Reviewed on 3 Jan, 2026
Wainscott Woods Retreat
Price was US$ 872, price is now US$ 813 per person
US$ 813
per person
Mar 19 - Mar 23
found 8 hours ago
Roundtrip flight included
Atlanta (ATL) to New York (LGA)
7/10 Good! (9 reviews)
Newly Renovated and extremely clean, well kept, and inviting rooms. Staff could not be nicer and more accommodating. Location is ideally situated close to lots of shops, Goldbergs for bagels, East Hampton Beaches etc. Highly recommend this accommodation to anyone staying in the area.
Reviewed on 15 Oct, 2025
Find the Best New Canaan Vacation Packages
New Canaan Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Westchester County Airport (HPN) |
Population | 19,700 |
Max Temp Winter | 35ºF |
Max Temp Summer | 80ºF |
Top Sights | Norwalk Maritime Aquarium, Compo Beach and Ridgefield Playhouse |
New Canaan Hotel Deals
Sonesta White Plains Downtown
66 Hale Ave White Plains NY
Fully refundableReserve now, pay when you stay
8.6/10 Excellent! (1,257 reviews)
The staff was wonderful. The room was very clean, the shower was amazing. However, note the self parking is $20 a night, there is not free self parking available.
Reviewed on 27 Jan, 2026
Baymont by Wyndham White Plains - Elmsford
540 Saw Mill River Rd Elmsford NY
Fully refundableReserve now, pay when you stay
8.2/10 Very Good! (1,511 reviews)
Clean room , Wonderful staff, and the room was very comfortable. Would definitely recommend going to this place!
Reviewed on 24 Jan, 2026
DoubleTree by Hilton Stamford
1 First Stamford Pl Stamford CT
Fully refundableReserve now, pay when you stay
7.4/10 Good! (1,004 reviews)
The position of the desk next to the air-conditioning vent is not ideal. Perhaps a switched position with the bureau/TV is better.
Reviewed on 27 Jan, 2026
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.
Discover the most popular places to visit in New Canaan
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.
Waveny Park
Waveny Park is just one of the places to see in New Canaan, so why not enjoy the other things to explore during your travels? While you're in the area, wander around the parks.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.