Madison Vacations from $419

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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.
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Save 100% on your flight
Price was $722, price is now $419 per person
$419
per person
Jan 7 - Jan 13
found 13 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
9.2/10 Wonderful! (1,621 reviews)
Staff was sub par for a 4 star hotel. Bartender and wait staff were more concerned about discussing issues with customers than actually serving people right in front of them. Front desk staff were very curt on the phone.

Reviewed on Oct 23, 2025

The McKernan Inn

The McKernan Inn

3 out of 5
Save 100% on your flight
Price was $888, price is now $542 per person
$542
per person
Jan 7 - Jan 13
found 13 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
9.2/10 Wonderful! (69 reviews)
Picturesque and quiet location! Laundry facilities! Staff was more than accommodating and a lovely ocean view with a delicious breakfast made for a memorable stay!

Reviewed on Oct 21, 2025

Cliff House Maine

Cliff House Maine

4.5 out of 5
Save 100% on your flight
Price was $1,753, price is now $1,151 per person
$1,151
per person
Jan 15 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Portland (PWM)
9.4/10 Exceptional! (1,016 reviews)
Absoltely incredible views- the cliffs were the perfect place to catch the sunrise. The restaurant was wonderful and the staff were super friendly and helpful. Extremely comfortable room and the hot tub and indoor pool were fantastic.

Reviewed on Oct 20, 2025

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

3 out of 5
Save 100% on your flight
Price was $1,236, price is now $848 per person
$848
per person
Dec 28 - Jan 2
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Lebanon (LEB)
9/10 Wonderful! (759 reviews)
The staff was very helpful, the place was comfortable with home amenities, view and property was breathtaking.

Reviewed on Oct 7, 2025

The Docent's Collection

The Docent's Collection

3.5 out of 5
Downtown Portland
Save 100% on your flight
Price was $920, price is now $647 per person
$647
per person
Jan 7 - Jan 13
found 13 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
9.6/10 Exceptional! (239 reviews)
Beautiful space. We will be back.

Reviewed on Oct 21, 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 Nov 9 to Nov 10
$107 total
Nov 9 - Nov 10
Total with taxes and fees
8.6/10 Excellent! (187 reviews)
Very quiet and comfortable stay. Only disappointment was that the resort charges additional rental for on site canoes. I would expect that to be included for a facility of this level.

Reviewed on Oct 9, 2025

Purity Spring Resort
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
$140 nightly
The price is $152 total per night from Nov 23 to Nov 24
$152 total
Nov 23 - Nov 24
Total with taxes and fees
8.2/10 Very Good! (1,030 reviews)
Did not ask for handicap room, but our stay was great. Enjoyed the upgraded outdoor area, convenience to shops. A beautiful spot, stayed here several times now. Only thought is, why the handicap room when we didn't request it? Will definitely return.

Reviewed on Oct 20, 2025

North Conway Grand Hotel
North Conway Mountain Inn

North Conway Mountain Inn

2.5 out of 5
2114 White Mountain Highway, North Conway, NH
$99 nightly
The price is $107 total per night from Oct 31 to Nov 1
$107 total
Oct 31 - Nov 1
Total with taxes and fees
8.6/10 Excellent! (1,159 reviews)
This Inn in very quaint. Perfec!

Reviewed on Oct 19, 2025

North Conway Mountain Inn
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.

Find the Best Madison Vacation Packages

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 $419 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

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