Madison Vacation Packages

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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.

Top Madison Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Cliff House Maine

Cliff House Maine

4.5 out of 5
Price was CA $1,513, price is now CA $1,227 per person
CA $1,227
per person
Oct 24 - Oct 26
found 10 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Portland (PWM)
9.4/10 Exceptional! (1,002 reviews)
What a Wonderful place!!!!

Reviewed on Aug. 28, 2025

The Docent's Collection

The Docent's Collection

3.5 out of 5
Downtown Portland
Price was CA $2,414, price is now CA $1,826 per person
CA $1,826
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9.6/10 Exceptional! (228 reviews)
Very modern and new condition. Digital key worked pretty well and convenient. Lots of good restaurants within walking distance. We enjoyed our stay.

Reviewed on Aug. 25, 2025

Hampton Inn Portland Downtown - Waterfront

Hampton Inn Portland Downtown - Waterfront

2.5 out of 5
Downtown Portland
Price was CA $1,935, price is now CA $1,572 per person
CA $1,572
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
8.8/10 Excellent! (1,006 reviews)
Hotel didn’t have water front view or I didn’t get one. View from my hotel room would have been great.

Reviewed on Aug. 28, 2025

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Price was CA $2,304, price is now CA $1,898 per person
CA $1,898
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9.2/10 Wonderful! (1,552 reviews)
Beautiful hotel, great location

Reviewed on Aug. 28, 2025

Canopy by Hilton Portland Waterfront

Canopy by Hilton Portland Waterfront

4 out of 5
Downtown Portland
Price was CA $2,243, price is now CA $1,852 per person
CA $1,852
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9.4/10 Exceptional! (1,009 reviews)
Near the waterfront. Great location in Old Port. We had a wonderful 2 night stay

Reviewed on Aug. 26, 2025

Ready to book your vacation to Madison?

 

Choose your dates

Madison Hotel Deals

Purity Spring Resort

Purity Spring Resort

2 out of 5
1251 Eaton Rd, Madison, NH
The price is CA $123 per night from Sep 8 to Sep 9
CA $123
CA $133 total
Sep 8 - Sep 9
includes taxes & fees
Purity Spring Resort
North Conway Mountain Inn

North Conway Mountain Inn

2.5 out of 5
2114 White Mountain Highway, North Conway, NH
Fully refundableReserve now, pay when you stay
The price is CA $136 per night from Sep 1 to Sep 2
CA $136
CA $148 total
Sep 1 - Sep 2
includes taxes & fees
8.6/10 Excellent! (1,104 reviews)
"Clean room, very friendly staff. Views were amazing."

Reviewed on Aug. 25, 2025

North Conway Mountain Inn
Green Granite Inn, Ascend Hotel Collection

Green Granite Inn, Ascend Hotel Collection

2.5 out of 5
1515 White Mountain Hwy, North Conway, NH
Fully refundableReserve now, pay when you stay
The price is CA $89 per night from Sep 4 to Sep 5
CA $89
CA $96 total
Sep 4 - Sep 5
includes taxes & fees
Green Granite Inn, Ascend Hotel Collection
See all 2,483 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Madison vacation package cost?
You'll find cheap prices from CA $1,227 on Expedia for your Madison escape. However, factors like your choice of hotel, the season and length of stay will influence how much your vacation to Madison costs.
What are the cheapest months to go to Madison?
March, April and November are great times to look for cheap Madison vacation packages. Travelling in less busy months means you can generally find better prices on accommodations and flights.
How many days is enough for Madison?
Madison vacations can be short or long, but to really get a feel for this destination, we reckon 2 days is a good ballpark. In this timeframe, you can fit in headline attractions like Conway Station and Conway Lake and seek out some hidden gems. Don't miss out on cool neighbourhoods such as Chocorua and Eaton either. If you plan wisely, you can even allow for a day trip from Madison too.
How to find the best Madison package deals?
Start your search for a Madison package deal by entering your destination and preferred trip dates under our "Packages" tab. Then select a few filters, like "Property type" and "Amenities," to fine-tune the results to your exact style. You can also sort by "Package discount" and browse offers that come with huge savings. If you don't find the perfect Madison package deal right away, just play around with your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Madison escape off to a flying start.
Is it cheaper to book a Madison vacation as a package?
You can enjoy significant savings on your next Madison getaway by booking a customized vacation package. Check the "Package" heading, then select your travel dates and destination to view the best flight and hotel prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Madison?
Score amazing discounts by reserving your flights ahead of time with Expedia. If being spontaneous is more your thing, grab one of our last-minute deals for a spur-of-the-moment Madison trip.
How to plan a trip to Madison?

  1. Pick the ideal time to travel: Your schedule, preferred season and the type of weather you like can all influence your decision on when to travel to Madison.
  2. Plan your budget wisely: As well as the cost of your hotel, you should factor in other expenses too. These include transportation, flights and food. Also, set aside a little extra for unexpected costs that could arise during your trip to Madison.
  3. Work out your trip length: Think about how much time you'd like to spend exploring Madison. Plan your days so you can get to all the experiences and attractions you're interested in without rushing.
  4. Combine your airfare and accommodations: Once you've settled on your trip dates and duration, book the right Madison vacation package for you.

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