
Madison Vacation Packages
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Save up to CA $1,096 when you book a flight and hotel together*
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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.

Hampton Inn Portland Downtown - Waterfront
Downtown Portland
Price was CA $1,500, price is now CA $1,246 per person
CA $1,246
per person
Nov 13 - Nov 20
found 16 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
8.8/10 Excellent! (1,004 reviews)
Great location and attentive staff service.
Reviewed on Aug. 23, 2025

The Weldon Hotel
Downtown Portland
Price was CA $2,274, price is now CA $1,594 per person
CA $1,594
per person
Nov 13 - Nov 20
found 16 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9.8/10 Exceptional! (68 reviews)
nice building walkable to shopping + dining
Reviewed on Aug. 22, 2025

The McKernan Inn
Price was CA $1,805, price is now CA $1,298 per person
CA $1,298
per person
Nov 13 - Nov 20
found 16 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9/10 Wonderful! (47 reviews)
Quiet and peaceful with views of the Bay. Easy to access and close to downtown Portland
Reviewed on Aug. 18, 2025

Portland Harbor Hotel
Downtown Portland
Price was CA $1,793, price is now CA $1,417 per person
CA $1,417
per person
Nov 13 - Nov 20
found 16 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9.2/10 Wonderful! (1,545 reviews)
Overall a great place and great location, did not like that the terrace could be privately booked and off limits, happened multiple times during our stay.
Reviewed on Aug. 22, 2025

The Docent's Collection
Downtown Portland
Price was CA $2,060, price is now CA $1,667 per person
CA $1,667
per person
Nov 13 - Nov 20
found 16 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9.6/10 Exceptional! (226 reviews)
I had a wonderful stay! The place was clean, cozy, and exactly as described. The location was perfect, which made everything smooth and easy. I’d happily stay here again and recommend it to anyone visiting Portland.
Reviewed on Aug. 22, 2025
Madison Hotel Deals

Purity Spring Resort
1251 Eaton Rd, Madison, NH
The price is CA $123 per night from Aug 25 to Aug 26
CA $123
CA $134 total
Aug 25 - Aug 26
includes taxes & fees
8.6/10 Excellent! (159 reviews)
"Nice restaurant on locations,"
Reviewed on Aug. 18, 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 $102 per night from Sep 2 to Sep 3
CA $102
CA $110 total
Sep 2 - Sep 3
includes taxes & fees
6.8/10 (1,214 reviews)
"👍"
Reviewed on Aug. 22, 2025

North Conway Grand Hotel
72 Common Court, North Conway, NH
Fully refundableReserve now, pay when you stay
The price is CA $208 per night from Sep 4 to Sep 5
CA $208
CA $259 total
Sep 4 - Sep 5
includes taxes & fees
8.2/10 Very Good! (1,001 reviews)
"Easy check in. Comfortable beds and nice bathrooms."
Reviewed on Aug. 22, 2025
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.
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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.