
Madison Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
Better together
Save up to CA $1,096 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place
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.


The Docent's Collection
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
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


Canopy by Hilton Portland Waterfront
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
Madison Hotel Deals

Purity Spring Resort
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

North Conway Mountain Inn
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

Green Granite Inn, Ascend Hotel Collection
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
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.
Frequently asked questions
Other vacations you might like
- January Vacations and Deals
- February Vacations and Deals
- March Vacations and Deals
- April Vacations and Deals
- May Vacations and Deals
- June Vacations and Deals
- July Vacations and Deals
- August Vacations and Deals
- September Vacations and Deals
- October Vacations and Deals
- November Vacations and Deals
- December Vacations and Deals
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.