Madison Vacation Packages

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  • Better together

    Save up to CAย $4,200 when you book a flight and hotel together*

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The Latest Madison Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • A dining area with a large window overlooking a cityscape, featuring a table with chairs and a meal.
    Jan 8 - Jan 11

    Hotel Riu Plaza Manhattan Times Square + Flight

    Manhattan
    3 nights
    4.0 star property
    9.2/10 - Wonderful (4,132 reviews)
    Roundtrip โ€ข Toronto (YTO) - New York (JFK)
    YYZ - LGA โ€ข Nonstop LGA - YYZ โ€ข Nonstop
    CAย $1,447
    CAย $936
    per traveller
    found 1 day ago
    Hotel Riu Plaza Manhattan Times Square
  • A historic building with ornate architectural details, multiple floors, and illuminated windows.
    Jan 8 - Jan 11

    The St. Regis New York + Flight

    Manhattan
    3 nights
    5.0 star property
    9.2/10 - Wonderful (294 reviews)
    Roundtrip โ€ข Toronto (YTO) - New York (JFK)
    YYZ - LGA โ€ข Nonstop LGA - YYZ โ€ข Nonstop
    CAย $3,758
    CAย $1,931
    per traveller
    found 1 day ago
    The St. Regis New York
  • A rooftop terrace with outdoor seating, a city view, and a brick building.
    Jan 14 - Jan 18

    JW Marriott Essex House New York + Flight

    Manhattan
    4 nights
    4.5 star property
    8.8/10 - Excellent (1,002 reviews)
    Roundtrip โ€ข Toronto (YTO) - New York (JFK)
    YYZ - LGA โ€ข Nonstop LGA - YYZ โ€ข Nonstop
    CAย $2,594
    CAย $1,411
    per traveller
    found 1 day ago
    JW Marriott Essex House New York
  • A rooftop terrace with outdoor seating, potted plants, and a cityscape view.
    Jan 7 - Jan 10

    The Mark + Flight

    Manhattan
    3 nights
    5.0 star property
    9.6/10 - Exceptional (723 reviews)
    Roundtrip โ€ข Vancouver (YVR) - New York (JFK)
    YVR - JFK โ€ข 1 stop JFK - YVR โ€ข 1 stop
    CAย $3,822
    CAย $2,480
    per traveller
    found 1 day ago
    The Mark
  • A building with a black awning displaying "THE WILLIAM" sign, a set of stairs leading to the entrance, and decorative iron railings.
    Jan 14 - Jan 18

    The William Hotel Midtown, New York + Flight

    Manhattan
    4 nights
    3.5 star property
    9.4/10 - Exceptional (293 reviews)
    "The bath towel shelf in the shower was so high up, I had to stand on my tippy toes to grab a towel and Iโ€™m 5ft 5in. Likewise, the little mirror by the entry door was hung at a height for a 6 foot man to check his hair. The pillows felt like swim floaties. Great location though. And no smartly situated outlets for recharging phone and laptop."
    Reviewed November 4, 2026
    Roundtrip โ€ข Toronto (YTO) - New York (JFK)
    YYZ - LGA โ€ข Nonstop LGA - YYZ โ€ข Nonstop
    CAย $1,457
    CAย $954
    per traveller
    found 1 day ago
    The William Hotel Midtown, New York

Where to stay in Madison

Find the best Madison areas and neighborhoods for the activities you enjoy most. Learn more about Madison
Learn more about Madison
A bridge with an American flag, a city skyline, and a waterfront park.

Brooklyn

This bustling borough has everything โ€” from pizza slices and pretzel vendors, to trendy galleries, and vintage stores -- all with killer views of the Manhattan skyline.
A city skyline with various high-rise buildings, including a distinctive skyscraper under construction, and a body of water in the foreground.

Midtown

Central portion of NYC, Midtown Manhattan boasts iconic landmarks like the Empire State Building and Times Square. Explore Broadway, Koreatown, and enjoy easy access to major transportation hubs like Grand Central Terminal.
A large glass-domed greenhouse surrounded by lush greenery and trees.

Bronx

New Yorkโ€™s northernmost borough is one of its most diverse, featuring beautiful natural spaces alongside engaging history and the rousing spirit of its residents.
A city skyline at dusk with illuminated bridges and buildings.

Williamsburg

Experience contemporary art, hipster culture, and vibrant nightlife in this Brooklyn gem. Discover cutting-edge galleries, trendy bars, and eclectic eateries for a taste of modern urban living.
A cityscape with a large park in the center, surrounded by high-rise buildings.

Central New York City

Known for its soaring skyscrapers and eye-catching views, there's plenty to explore in Central New York City. Check out top attractions like Times Square and Rockefeller Center, and jump on the metro at 49th St. Station or 50 St. Station (Broadway) to see more of the city.

Madison Hotel Deals

A rooftop terrace with a city skyline view at sunset, featuring a sofa, a coffee table, and potted plants.

PUBLIC, an Ian Schrager hotel

PUBLIC, an Ian Schrager hotel
4.0 star property
13.4 km from Madison
8.8 out of 10, Excellent, (4,087 reviews)
The price is CAย $426
CAย $566 total
includes taxes & fees
Nov 24 - Nov 25
PUBLIC, an Ian Schrager hotel
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.
See all properties in Madison
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.