East Madison Vacations from $527

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Your East Madison Vacation

The hassle-free way to experience this exciting city is with a tailor-made East Madison vacation package. Stay in the neighborhood of Chocorua, which is great for nature, families and views or go someplace else — our package deals are all about you. There's loads to see during your trip to East Madison, including King Pine Ski Area and Madison Boulder. Stop daydreaming and start traveling. Check out the broad range of options on Expedia today and put your East Madison vacation plans in motion!

The Latest East Madison Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • A well-lit living room with a fireplace, comfortable seating, and a large mirror.
    Feb 2 - Feb 5

    Blind Tiger Portland – Carleton Street + Flight

    West End
    3 nights
    3.5 star property
    9.6/10 - Exceptional (137 reviews)
    "Quick responses by staff! Comfortable bed! Gorgeous amenities! Loved the location was right down from Tandem Coffee!"
    Reviewed October 21, 2026
    Roundtrip • Orlando (MCO) - Portland (PWM)
    MCO - PWM • 1 stop PWM - MCO • Nonstop
    $674
    $527
    per traveler
    found 1 day ago
    Blind Tiger Portland – Carleton Street
  • A spacious living room with a large dining table, comfortable seating, and large windows offering views of the city.
    Feb 2 - Feb 5

    The Docent's Collection at 121 Middle Street + Flight

    Downtown Portland
    3 nights
    3.5 star property
    9.6/10 - Exceptional (430 reviews)
    "The room was spacious, super clean, and well equipped. Good location in the Port. Nearby parking seems plentiful. The Docent calls itself an "aparthotel," meaning there aren't really hotel amenities. A lot of the communication with staff is done by text. Although, there was a human person at the door for most of our stay. Great choice, particularly for a long term stay given the swell kitchen, if you don't mind the concept."
    Reviewed November 10, 2026
    Roundtrip • Orlando (MCO) - Portland (PWM)
    MCO - PWM • 1 stop PWM - MCO • Nonstop
    $815
    $654
    per traveler
    found 1 day ago
    The Docent's Collection at 121 Middle Street
  • A spacious kitchen with a central island, wooden bar stools, and a long dining table.
    Feb 2 - Feb 5

    Blind Tiger Portland - Danforth Street. + Flight

    West End
    3 nights
    3.5 star property
    9.6/10 - Exceptional (206 reviews)
    Roundtrip • Orlando (MCO) - Portland (PWM)
    MCO - PWM • 1 stop PWM - MCO • Nonstop
    $730
    $600
    per traveler
    found 1 day ago
    Blind Tiger Portland - Danforth Street.
  • An outdoor seating area with a fire feature, comfortable seating, and a view of a waterfront.
    Dec 30 - Jan 5

    Canopy by Hilton Portland Waterfront + Flight

    Downtown Portland
    6 nights
    4.0 star property
    9.4/10 - Exceptional (1,005 reviews)
    Roundtrip • New York (NYC) - Portland (PWM)
    EWR - PWM • Nonstop PWM - EWR • Nonstop
    $1,307
    $1,103
    per traveler
    found 13 hours ago
    Canopy by Hilton Portland Waterfront
  • A spacious living room with a large window, a round coffee table, and two wooden chairs.
    Feb 2 - Feb 5

    The Docent's Collection at 178 Middle Street + Flight

    Downtown Portland
    3 nights
    3.5 star property
    9.6/10 - Exceptional (87 reviews)
    "This could not have been a better location to all the nighttime eateries and shopping. The property is beautiful! Way more than just a hotel. Order in and enjoy the beautiful kitchen and high-end apartment feeling."
    Reviewed November 11, 2026
    Roundtrip • Orlando (MCO) - Portland (PWM)
    MCO - PWM • 1 stop PWM - MCO • Nonstop
    $950
    $803
    per traveler
    found 1 day ago
    The Docent's Collection at 178 Middle Street

East Madison Hotel Deals

Room

Snowvillage Inn

Snowvillage Inn
4.0 star property
3.5 mi from East Madison
9.0 out of 10, Wonderful, (322 reviews)
"Overall, we enjoyed our stay. A few things to note: -There are no televisions in the rooms! There are games and books to borrow, but plan ahead if you need a TV! -There seemed to be no staff around, except for the cook (shout out to Brendan!!) who did his best until the server showed up (at 6:00) -The water in our shower was not hot at all... Lukewarm at best. Disappointing. -Die to low staffing, there was no room turnover. No new towels, empty trash can or replacement coffee items. The...
$97 nightly
The price is $105
Nov 17 - Nov 18
Total with taxes and fees
Snowvillage Inn
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 East Madison

Frequently Asked Questions

How much does an East Madison vacation package cost?

You'll find cheap prices from $527 on Expedia for your East Madison escape. However, a range of factors like the season, choice of hotel and length of stay will determine how much your vacation to East Madison costs.

What are the cheapest months to go to East Madison?

February, May and November are the best times to look for cheap East Madison vacation packages. Opting to travel in quieter months means you can usually find better prices on hotels and flights.

How many days is enough for East Madison?

With a well-organized schedule, you can easily hit the top East Madison sights in a few days. But if you prefer to discover lesser-known spots or go on day tours, consider booking your East Madison vacation for longer.

How to find the best East Madison package deals?

Finding a cheap East Madison package deal is a cinch with Expedia. Once you've entered your trip dates and destination under our "Packages" tab, set your maximum budget, add a couple of filters and see what's available. You can personalize your search by "Area," "Amenities," "Property type" and more. Sort the results by "Price: low to high" to discover the most pocket-friendly East Madison package deals. Want a simple trick to get the biggest savings? Have some flexibility with your departure dates and consider traveling on a weekday, when prices are usually lower.

Is it cheaper to book an East Madison vacation as a package?

Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your car rental, flight and hotel into one great-value price and you could save hundreds of dollars. You'll typically land a better deal than booking each component separately. And you'll still get the flexibility to create a personalized East Madison vacation by choosing your favorite airline, accommodation type and car class.

When to book a vacation package to East Madison?

Secure incredible discounts by reserving your flights in advance with Expedia. If spontaneity is more your style, take advantage of our last-minute deals for an impromptu East Madison escape.

Does Expedia offer Book Now, Pay Later East Madison vacation packages?

Jet off on your perfect escape to East Madison with help from our Book Now, Pay Later vacations. There's no need to save up or wait until your next payday — we've joined forces with online lender Affirm to give you more flexibility with your finances. Our vacation packages with payment plans let you split the cost over 3, 6 or 12 months. With no hidden charges or late payment fees, it's easy to stay on budget and snap up travel deals before they disappear.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.