A highway surrounded by autumn foliage.

New Canaan Vacations from $959

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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

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    Where to stay near New Canaan

    New Canaan offers a charming blend of outdoor adventures and cultural experiences, making it an ideal New England destination. Explore nearby Berkshire Village for quaint shops and scenic views, or head to Rocky Hill for family-friendly activities. Enjoy a perfect getaway filled with romance and recreation.

    A cityscape with a river, modern buildings, and green spaces.

    A sailboat on a calm sea during sunset.

    An aerial view of a coastal town with a marina, waterfront homes, and a bridge connecting to the mainland.

    A marina with boats docked, surrounded by rocks and greenery, with buildings and a sunset in the background.

    A tranquil lake with a small island featuring a house and a dock extending into the water.

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    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.

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    A wooden pier leading to a stone building with a lighthouse, surrounded by greenery and a calm body of water.

    A historic stone building with a lighthouse on top, a smaller adjacent structure, and a grassy field in the foreground.

    A person in blue attire on a rocky shore with a body of water and a clear sky in the background.

    A marina at sunset with boats docked, a bridge, and buildings in the background.

    A pier extending into calm waters at dusk with a stone walkway and railings.

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    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.

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    A cannon on a stone pedestal by the sea.

    A calm river reflecting buildings and trees, with a clear sky above.

    A cannon on a stone pedestal by the sea with a person standing in the background.

    A beach at sunset with a wooden fence, picnic tables, and people walking.

    A person standing on a rocky shoreline with green moss, overlooking a calm sea under a cloudy sky.

    Photo by Marina Timo

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    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.

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    A calm harbor with boats, a pier, and houses along the shoreline.

    Photo by Tim Rousseau

    Two wooden benches facing a calm body of water under a clear sky.

    A sailboat on calm water with a clear sky.

    Photo by Tim Rousseau

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    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.

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    A building with the inscription "Wilton Town Hall" above a row of columns.

    A large white house with a stone wall in front, surrounded by trees with autumn leaves.

    A forest with a stone wall and fallen leaves.

    A wooden bridge in a forest with autumn leaves and moss-covered rocks.

    A calm lake surrounded by dense forests.

    Photo by Lori Buchanan

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    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.

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    Discover the most popular places to visit in New Canaan

    The Glass House

    Rating: 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.

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    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.

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    Waveny Park

    Rating: 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.

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    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.

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    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.

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    Carriage Barn Arts Center

    Enjoy an outing to Carriage Barn Arts Center during your stay in New Canaan. Discover the coral reefs while you're in the area.

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    God's Acre

    God's Acre is just one of the places to see in New Canaan, so why not enjoy the other things to explore during your travels? Discover the coral reefs while you're in the area.

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    Kiwanis Park

    Kiwanis 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 natural setting.

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    New Canaan Hotel Deals

    The Watershed

    A modern living room with a stone fireplace, large windows, and a cozy seating area.
    • Address: 353 Main Ave, Norwalk, CT, 06851, US
    • Location: 3.6 mi from New Canaan
    • Star rating: 3.5/5
    • Guest rating: 9.2/10 (Wonderful, 1002 reviews)
    • Price: $159 nightly, $183 total, Dec 13 - Dec 14, Total with taxes and fees
    • Review: Beautiful hotel. Nice staff & well appointed rooms! Continental breakfast could be a bit better. Black teabags are a must for those that don't like herbal ....:)

    Norwalk Inn & Conference Center

    A sign for Norwalk Inn, Adams Rib Restaurant, with a brick wall and autumn foliage in the background.
    • Address: 99 East Avenue, Norwalk, CT, 06851, US
    • Location: 5 mi from New Canaan
    • Star rating: 4/5
    • Guest rating: 8.8/10 (Excellent, 1498 reviews)
    • Price: $115 nightly, $133 total, Nov 29 - Nov 30, Total with taxes and fees
    • Review: Beautiful and close to great restaurants and shopping, friendly style comfortable room

    Hilton Garden Inn Norwalk

    A spacious living area with a large potted plant, a sofa, a chair, and a hanging lamp.
    • Address: 560 Main Ave, Norwalk, CT, 06851, US
    • Location: 3.8 mi from New Canaan
    • Star rating: 3/5
    • Guest rating: 8.2/10 (Very good, 1003 reviews)
    • Price: $135 nightly, $155 total, Dec 13 - Dec 14, Total with taxes and fees
    • Review: We had a weird room on the first floor. Next to an entrance. Wheel chair accessible shower. The whole floor would get wet. It was noisy. I feel like they give these rooms to people who book thru other platforms.

    Courtyard by Marriott Norwalk

    A modern Courtyard by Marriott hotel with a well-lit entrance, a covered outdoor area, and a landscaped garden.
    • Address: 474 Main Ave, Norwalk, CT, 06851, US
    • Location: 3.6 mi from New Canaan
    • Star rating: 3/5
    • Guest rating: 8.8/10 (Excellent, 1001 reviews)
    • Price: $152 nightly, $175 total, Nov 22 - Nov 23, Total with taxes and fees

    EVEN Hotel Norwalk by IHG

    An outdoor seating area with a fire pit surrounded by wooden chairs and blue cushions.
    • Address: 426 Main Ave, Route 7, Norwalk, CT, 06851, US
    • Location: 3.6 mi from New Canaan
    • Star rating: 3.5/5
    • Guest rating: 8.4/10 (Very good, 1199 reviews)
    • Price: $119 nightly, $137 total, Dec 13 - Dec 14, Total with taxes and fees

    Residence Inn by Marriott Norwalk

    A modern lounge area with a stone fireplace, leather seating, and large windows offering a view of the city.
    • Address: 45 South Main Street, Norwalk, CT, 06854, US
    • Location: 5.2 mi from New Canaan
    • Star rating: 3/5
    • Guest rating: 9/10 (Wonderful, 438 reviews)
    • Price: $169 nightly, $195 total, Dec 6 - Dec 7, Total with taxes and fees
    • Review: Staff at desk very knowledgable about stores and resturaunts in the area

    The Armon Stamford Hotel & Conference

    A spacious atrium with a central garden, multiple floors, and a distinctive white gazebo.
    • Address: 2701 Summer St, Stamford, CT, 06905, US
    • Location: 6 mi from New Canaan
    • Star rating: 2.5/5
    • Guest rating: 7.8/10 (Good, 1005 reviews)
    • Price: $174 nightly, $200 total, Nov 25 - Nov 26, Total with taxes and fees
    • Review: Muy bueno

    Delamar Westport

    A bar with a stone wall, multiple shelves of bottles, and bar stools.
    • Address: 1595 Post Rd E, Westport, CT, 06880, US
    • Location: 9.7 mi from New Canaan
    • Star rating: 4/5
    • Guest rating: 9.6/10 (Exceptional, 222 reviews)
    • Price: $214 nightly, $244 total, Nov 19 - Nov 20, Total with taxes and fees
    • Review: elegant and spacious room. The bed was fabulous, the bathroom was fabulous, greeted with Prosecco and just love this modern hotel. I will be back.

    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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    Frequently Asked Questions

    How much does a New Canaan vacation package cost?

    You can snap up a vacation package to this destination from $959 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.

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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.