Madison Vacations from $425

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Your Madison Vacation

From its highlights to its hidden delights, this city is best experienced with a Madison vacation package. Find somewhere to stay in Chocorua, which is great for nature, families and views. Make your trip to Madison even more fulfilling by including some sightseeing. King Pine Ski Area, Saco River and Chocorua Lake are some of the big attractions worth exploring. Expedia can help you escape the everyday. Tailor your vacation to Madison to suit your style of travel, whatever that may be.

The Latest Madison vacation packages

Price found within the past 48 hours. Click for updated prices.
Nonantum Resort

Nonantum Resort

3.5 out of 5
Save 100% on your flight
Price was $617, price is now $425 per person
$425
per person
Nov 7 - Nov 10
found 21 hours ago
Roundtrip flight included
Nashville (BNA) to Portland (PWM)
9.2/10 Wonderful! (802 reviews)
The stay was amazing, only issue we had was that the walls were very thin and there were hardwood floors. Heard everything going on around us including the person in the room above us on the first night walking back and forth and continuously turning the bath faucet on and off for hours until past 2 am. Kept us awake most of the night.

Reviewed on Oct 6, 2025

Cliff House Maine

Cliff House Maine

4.5 out of 5
Save 100% on your flight
Price was $1,122, price is now $729 per person
$729
per person
Nov 7 - Nov 10
found 21 hours ago
Roundtrip flight included
Nashville (BNA) to Portland (PWM)
9.4/10 Exceptional! (1,007 reviews)
Beautiful clean room with the most amazing views! Staff is very friendly and shoutout to Mark and Mariam for welcoming my kids with some fun snacks after our long trip to get here! Words can’t describe our experience at the Cliff House.. just WOW!

Reviewed on Oct 4, 2025

Inn By The Sea

Inn By The Sea

4 out of 5
Price was $1,332, price is now $1,041 per person
$1,041
per person
Nov 14 - Nov 19
found 1 day ago
Roundtrip non-stop flight included
Austin (AUS) to Portland (PWM)
9.4/10 Exceptional! (281 reviews)
Absolutely 5 star. Best bed I’ve slept in at a hotel bar none.

Reviewed on Sep 10, 2025

Kennebunkport Captains Collection

Kennebunkport Captains Collection

4.5 out of 5
Price was $1,124, price is now $901 per person
$901
per person
Nov 14 - Nov 19
found 1 day ago
Roundtrip non-stop flight included
Austin (AUS) to Portland (PWM)
9.4/10 Exceptional! (622 reviews)
Quaint, historical, friendly and helpful staff. Loved our stay here!

Reviewed on Oct 7, 2025

The Weldon Hotel

The Weldon Hotel

4.5 out of 5
Downtown Portland
Price was $1,042, price is now $847 per person
$847
per person
Dec 29 - Jan 3
found 1 day ago
Roundtrip non-stop flight included
Nashville (BNA) to Portland (PWM)
9.8/10 Exceptional! (79 reviews)
Great spot, large space, cool design, clean, easy to walk all over town.

Reviewed on Oct 1, 2025

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Madison Hotel Deals

Purity Spring Resort

Purity Spring Resort

2 out of 5
1251 Eaton Rd, Madison, NH
Fully refundableReserve now, pay when you stay
$99 nightly
The price is $107 total per night from Oct 21 to Oct 22
$107 total
Oct 21 - Oct 22
Total with taxes and fees
8.6/10 Excellent! (182 reviews)
"Great location, camp rooms need updating"

Reviewed on Oct 2, 2025

Purity Spring Resort
North Conway Mountain Inn

North Conway Mountain Inn

2.5 out of 5
2114 White Mountain Highway, North Conway, NH
$89 nightly
The price is $97 total per night from Oct 26 to Oct 27
$97 total
Oct 26 - Oct 27
Total with taxes and fees
8.8/10 Excellent! (1,126 reviews)
"Great place! So nice + clean! Friendly staff! Shopping is all around + the views of the mountains are gorgeous!!!"

Reviewed on Oct 7, 2025

North Conway Mountain Inn
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
$142 nightly
The price is $155 total per night from Nov 6 to Nov 7
$155 total
Nov 6 - Nov 7
Total with taxes and fees
8.2/10 Very Good! (1,001 reviews)
"The room was clean,but I found the bed very uncomfortable. The mattress was very hard."

Reviewed on Oct 2, 2025

North Conway Grand Hotel
See all 2,424 properties in 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.

Madison Essential Information

Language
English
Currency
U.S dollars
Population
2,100
Max Temp Winter
30ºF
Max Temp Summer
75ºF
Top Sights
Cranmore Mountain Resort, Kahuna Laguna and Echo Lake State Park

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Frequently asked questions

How much does a Madison vacation package cost?
You'll find cheap prices from $425 on Expedia for your Madison getaway. However, a range of factors like the season, length of stay and your choice of hotel will influence how much your vacation to Madison costs.
What are the cheapest months to go to Madison?
If you're looking to book a cheap Madison vacation package, consider planning a trip in February, May and November. You'll typically find better prices on flights and hotels during these months — ideal for a budget-friendly getaway.
How many days is enough for Madison?
With a well-planned itinerary, you can easily visit the most popular Madison attractions in a handful of days. But if you want to discover hidden spots or go on day trips, consider booking your Madison vacation for longer.
How to find the best Madison package deals?
Use Expedia's handy filters to find some terrific Madison package deals. When you begin your search, just set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your adventure for midweek, or browse for Madison package deals in the off-season. Switch up your travel dates and you may score even bigger discounts. As a rule of thumb, it's typically best to lock in your vacation package well in advance.
Is it cheaper to book a 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 enjoy significant savings. You'll generally score a better deal than booking each component individually. And you'll still get the freedom to create a customized Madison vacation by choosing your favorite type of stay, airline and car class.
When to book a vacation package to Madison?
If you have your Madison vacation dates confirmed, book as soon as you can to bag some terrific deals. With Expedia, you can generally reserve some flights up to a year in advance. Prefer spontaneous getaways? Our last-minute deals are perfect for impromptu escapes.
Does Expedia offer Book Now, Pay Later Madison vacation packages?
Jet off on your perfect escape to Madison with help from our Book Now, Pay Later vacations. No need to save like crazy or hold off until your next paycheck — we've joined forces with online lender Affirm to give you more flexibility and choice. Our vacation packages with payment plans allow you to split the cost over 3, 6 or 12 months. With no late payment fees or extra charges, it's a breeze to stay on budget and snap up cheap deals while they last.

Explore a world of travel with Expedia

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.