East Madison Vacations from $491

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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.
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Price was $756, price is now $491 per person
$491
per person
Mar 18 - Mar 22
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Portland (PWM)
9.2/10 Wonderful! (1,668 reviews)
Room was perfect! Super clean. Comfortable. Great location. Front desk employees were informative and so friendly at check in. Restaurant was delicious. Only downside was an extremely rude server (possibly manager, as he was not wearing a uniform) that waited on us during dinner.

Reviewed on Jan 8, 2026

The McKernan Inn

The McKernan Inn

3 out of 5
Price was $793, price is now $543 per person
$543
per person
Mar 18 - Mar 22
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Portland (PWM)
9/10 Wonderful! (83 reviews)
Gorgeous grounds and venue with a beautiful oceanfront view. Plenty of parking as part of SMCC campus. Short drive to downtown Portland and lots of stores around in South Portland. Very unique experience, would stay again without hesitation!

Reviewed on Dec 27, 2025

The Docent’s Collection – Thompson Block

The Docent’s Collection – Thompson Block

3.5 out of 5
Downtown Portland
Price was $861, price is now $635 per person
$635
per person
Mar 18 - Mar 22
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Portland (PWM)
9.6/10 Exceptional! (249 reviews)
This was a great stay! Had everything we wanted. Location was excellent.

Reviewed on Dec 24, 2025

Cliff House Maine

Cliff House Maine

4.5 out of 5
Bald Head
Save 100% on your flight
Price was $1,458, price is now $1,082 per person
$1,082
per person
Apr 3 - Apr 6
found 8 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
9.4/10 Exceptional! (1,001 reviews)
The room along with the view was spectacular - Beautifully decorated - Clean - Crisp - The Staff - Beyond Helpful!! The location overlooking the Atlantic Ocean even this time of year with the sun and the ocean waves hitting the rocks was like out of a movie!! Their restaurants 5 star in my opinion!! Just the people they have working looking out for you and making sure you are having an experience of a lifetime!! Thank you again Cliff House - See you very soon!!!

Reviewed on Jan 6, 2026

84 Main

84 Main

4 out of 5
Price was $694, price is now $522 per person
$522
per person
Feb 12 - Feb 16
found 22 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Portland (PWM)
10/10 Exceptional! (52 reviews)
This property was absolutely beautiful and well maintained! Right in the heart of Kennebunk within walking distance to great restaurants!!

Reviewed on Oct 26, 2025

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East Madison Hotel Deals

North Conway Grand Hotel

North Conway Grand Hotel

4 out of 5
72 Common Court North Conway NH
Fully refundableReserve now, pay when you stay
$122 nightly
The price is $133 total per night from Jan 11 to Jan 12
$133 total
Jan 11 - Jan 12
Total with taxes and fees
8.2/10 Very Good! (1,012 reviews)
It was great

Reviewed on Jan 5, 2026

North Conway Grand Hotel
Grand Summit Hotel at Attitash

Grand Summit Hotel at Attitash

3 out of 5
104 Grand Summit Road Bartlett NH
Fully refundableReserve now, pay when you stay
$126 nightly
The price is $137 total per night from Jan 11 to Jan 12
$137 total
Jan 11 - Jan 12
Total with taxes and fees
8.4/10 Very Good! (1,006 reviews)
While the facility was a bit understaffed, everyone working was prompt, friendly, and working incredibly hard to keep things moving smoothly!

Reviewed on Jan 2, 2026

Grand Summit Hotel at Attitash
Eastern Inn & Suites

Eastern Inn & Suites

2 out of 5
2955 White Mountain Highway, Route 16 North Conway NH
Fully refundableReserve now, pay when you stay
$146 nightly
The price is $158 total per night from Jan 12 to Jan 13
$158 total
Jan 12 - Jan 13
Total with taxes and fees
8.4/10 Very Good! (1,017 reviews)
This is a great place to stay a few nights and is really easy to get too. Also a lot of great restaurants nearby and very close to downtown. Staff could not be any nicer and there's always hot coffee by the front desk

Reviewed on Jan 5, 2026

Eastern Inn & Suites
See all 1,824 properties in East Madison
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.

Find the Best East Madison Vacation Packages

East Madison Essential Information

Language
English
Currency
U.S dollars
Max Temp Winter
30ºF
Max Temp Summer
75ºF

East Madison Ski Vacation Packages

Go your own way with one of our East Madison ski vacation packages. Whether you're seeking thrills on the mountain, some respite at altitude or a little of both, your ultimate escape starts with Expedia. Journey to East Madison between December and March and you'll discover around 17 runs operating at this top ski destination in United States of America. Enjoy tree, downhill and backcountry skiing or if you're a newbie, sign up for a lesson in a beginners' area. Need poles, a jacket and other items? You'll find everything in the ski village. There's also a spa and wellness center to make use of here. After a long day of skiing, your tired legs will welcome a relaxing massage. The whole gang will be entertained on your family ski vacation in East Madison, with thrilling activities such as nordic skiing, night skiing and snowboarding on the menu too.

How To Get Around

If you've booked one of our East Madison vacation packages, you'll likely be jetting into Portland International Jetport. From here, it's one and a half hours to reach this well-known ski area. It takes 15 minutes to travel to the runs from the middle of East Madison, and free parking is available. If you're driving in winter, tire chains are recommended. With season-pass, weekend-pass, full-day and half-day ticket types on offer, your dream ski vacation is as easy as choosing the right option for you. Planning your escape with Expedia is easy too. Look through our East Madison ski package deals and combine your hotel, flights and car rental to make some big savings.

East Madison Resort Ski Info

Average yearly snowfall
10 ft
Elevation of lowest ski lift
741 ft
Cost of 1-day lift pass
Under $75
Easy runs
7
Moderate runs
5
Advanced runs
4
Longest run
0.39 mi

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Frequently asked questions

How much does an East Madison vacation package cost?
You'll find cheap prices from $491 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.

Explore a world of travel with Expedia

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