East Madison Vacations from $780

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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
Save 100% on your flight
Price was $1,126, price is now $780 per person
$780
per person
May 28 - Jun 1
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Portland (PWM)
9.2/10 Wonderful! (1,765 reviews)
Business facilities were perfect. Front desk man Roman was an all star helping us out. Whole stay was 100/100

Reviewed on Mar 4, 2026

The Weldon Hotel

The Weldon Hotel

4.5 out of 5
Downtown Portland
Save 100% on your flight
Price was $1,455, price is now $989 per person
$989
per person
May 28 - Jun 1
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Portland (PWM)
9.8/10 Exceptional! (93 reviews)
Location is excellent. Short walking distance to every good restaurant and shop. The property was very nice and clean. The kitchen is very well equipped. The gym is very good sized for the size of the apartment building with 13 units in it. The management’s communication was prompt and friendly and responded to all of our wishes. However, the place is advertised as a hotel, but don’t expect services as in a hotel. It resembles more a short term rental home - no cleaning service and no lobby. Otherwise everything was very nice in the apartment and we had a great time.

Reviewed on Jan 3, 2026

Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
West End
Save 100% on your flight
Price was $1,357, price is now $1,001 per person
$1,001
per person
May 28 - Jun 1
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Portland (PWM)
9.6/10 Exceptional! (175 reviews)
The whole was cozy! Well curated style and knowledgeable staff.

Reviewed on Jan 5, 2026

Cliff House Maine

Cliff House Maine

4.5 out of 5
Bald Head
Save 100% on your flight
Price was $1,550, price is now $1,161 per person
$1,161
per person
May 7 - May 10
found 5 hours ago
Roundtrip flight included
Minneapolis (MSP) to Portland (PWM)
9.4/10 Exceptional! (1,001 reviews)
Great hotel with super nice views!

Reviewed on Mar 1, 2026

Inn By The Sea

Inn By The Sea

4 out of 5
Save 100% on your flight
Price was $1,417, price is now $1,079 per person
$1,079
per person
May 28 - Jun 1
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Portland (PWM)
9.4/10 Exceptional! (300 reviews)
Such a beautiful place, great to walk on beach, nice view, staff great.. cozy place.. so well decorated.. highly recommend for a nice quiet get away

Reviewed on Mar 4, 2026

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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
$133 nightly
The price is $145 total per night from Mar 11 to Mar 12
$145 total
Mar 11 - Mar 12
Total with taxes and fees
8.4/10 Very Good! (1,014 reviews)
Great stay, outdoor pool and hot tubs were fantastic.

Reviewed on Mar 5, 2026

North Conway Grand Hotel
Cambria Hotel North Conway

Cambria Hotel North Conway

3 out of 5
1858 White Mountain Highway North Conway NH
Fully refundable
$101 nightly
The price is $110 total per night from Mar 26 to Mar 27
$110 total
Mar 26 - Mar 27
Total with taxes and fees
9/10 Wonderful! (522 reviews)
This is a nice new hotel that is centrally located. I prepaid for breakfast and was told they were too busy to take any orders when we went to eat. They offered a refund (after I asked the Front desk for it) which I never received. This is full hotel vibe if that is what you are after. Clean and ...

Reviewed on Mar 3, 2026

Cambria Hotel North Conway
North Conway Mountain Inn

North Conway Mountain Inn

2.5 out of 5
2114 White Mountain Highway North Conway NH
$76 nightly
The price is $82 total per night from Mar 13 to Mar 14
$82 total
Mar 13 - Mar 14
Total with taxes and fees
8.8/10 Excellent! (1,217 reviews)
Basic room, great view of the mountains, staff were very nice, great price and very clean.

Reviewed on Mar 3, 2026

North Conway Mountain Inn
See all 1,831 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 $780 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.

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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.