Title: Madison Vacation Packages & Trips 2026 from CA $1,346 | Expedia.ca [Hotels in Madison](https://expedia.ca/Madison-Hotels.d601609.Travel-Guide-Hotels)[Vacation Rentals in Madison](https://expedia.ca/Madison-Vacation-Rentals.d601609.Travel-Guide-VacationRentals)[Madison Car Rentals](https://expedia.ca/Car-Rentals-In-Madison.d601609.Car-Rental-Guide) ![](https://images.trvl-media.com/place/601609/2ae5725f-4b6e-478b-ac11-6a0fb3add90d.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # 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](https://www.expedia.ca/King-Pine-Ski-Area-New-Hampshire.d6079713.Vacation-Attraction), [Saco River](https://www.expedia.ca/Saco-River-United-States-of-America.d553248621555565606.Vacation-Attraction) and [Chocorua Lake](https://www.expedia.ca/Chocorua-Lake-Chocorua.d553248621562854430.Vacation-Attraction) 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. ![Portland Harbor Hotel](https://images.trvl-media.com/lodging/1000000/900000/898700/898621/1a7f326f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Portland Harbor Hotel Downtown Portland CA $1,346 per person May 15 - May 18 found 19 hours ago Roundtrip non-stop flight included Toronto (YYZ) to Portland (PWM) 9.2/10 Wonderful! (1,776 reviews) We could have moved right in and been happy for life. Flawless. Reviewed on Mar 30, 2026 ![Blind Tiger Portland - Danforth Street.](https://images.trvl-media.com/lodging/1000000/210000/200300/200246/7a3d1c09_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Blind Tiger Portland - Danforth Street. West End CA $1,788 per person May 15 - May 18 found 19 hours ago Roundtrip non-stop flight included Toronto (YYZ) to Portland (PWM) 9.6/10 Exceptional! (175 reviews) The Blind Tiger was one of the best accommodations I've ever stayed in! The location was perfect – far enough away from the "bustle" of downtown but close enough to walk to many spots (Smalls was a favorite!). The daily breakfast was so great and the room, my goodness! Adorable, perfect, comfortable... best sleep of my life! Maggie was so helpful and accommodating and made our stay really special. All in all, highly recommend! Reviewed on Mar 10, 2026 ![The Docent's Collection at 121 Middle Street](https://images.trvl-media.com/lodging/39000000/38780000/38770100/38770068/148140d6_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Docent's Collection at 121 Middle Street Downtown Portland CA $1,541 per person May 15 - May 18 found 19 hours ago Roundtrip non-stop flight included Toronto (YYZ) to Portland (PWM) 9.6/10 Exceptional! (275 reviews) So spacious, decor is modern yet warm. Staff super friendly and helpful. Perfect location for concerts at Merrill, short walk. Reviewed on Mar 28, 2026 ![Portland Regency Hotel & Spa](https://images.trvl-media.com/lodging/1000000/930000/920100/920050/d87c36dc_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Portland Regency Hotel & Spa Downtown Portland CA $1,377 per person May 15 - May 18 found 19 hours ago Roundtrip non-stop flight included Toronto (YYZ) to Portland (PWM) 9.4/10 Exceptional! (1,599 reviews) Very nice hotel, located in the center of Portland. Will stay there again. Reviewed on Apr 1, 2026 ![Kennebunkport Captains Collection](https://images.trvl-media.com/lodging/14000000/13280000/13279300/13279259/c4a328d8_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Kennebunkport Captains Collection CA $1,351 per person May 15 - May 18 found 19 hours ago Roundtrip non-stop flight included Toronto (YYZ) to Portland (PWM) 9.4/10 Exceptional! (686 reviews) Historic, cozy, and charming mansions and rooms...our stay was amazing. Reviewed on Mar 15, 2026 ## Ready to book your vacation to Madison? Choose your dates ## Madison Hotel Deals ![Purity Spring Resort](https://images.trvl-media.com/lodging/65000000/64620000/64619400/64619336/89f00817_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Purity Spring Resort 1251 Eaton Rd Madison NH 8.8/10 Excellent! (196 reviews) A wonderful oasis. Skiing, skating, swimming, restaurant and tavern, cross country ski trails, snowshoe trails and exercise room/hot tub all a minutes walk away in a picturesque valley setting. Reviewed on Mar 13, 2026 [Get rates](https://expedia.ca/Hotel-Search?startDate=15%2F04%2F2026&endDate=16%2F04%2F2026&selected=64619336&PinnedHotelID=64619336&HadPinnedHotel=true®ionId=601609) [](https://expedia.ca/Hotel-Search?startDate=15%2F04%2F2026&endDate=16%2F04%2F2026&selected=64619336&PinnedHotelID=64619336&HadPinnedHotel=true®ionId=601609) ![North Conway Grand Hotel](https://images.trvl-media.com/lodging/1000000/700000/694700/694639/8c5fc8a6_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### North Conway Grand Hotel 72 Common Court North Conway NH CA $145 CA $191 total Apr 26 - Apr 27 includes taxes & fees 8.4/10 Very Good! (1,024 reviews) Staff was all helpful and kind for the most part. Their spa I would not recommend at all. Had a horrible first time experience at a couples massage. Was asked at the beginning of massage if there were problem areas to focus on. I told my therapist my forearms. When I brought up at the end of my massage ... Reviewed on Apr 1, 2026 [](https://expedia.ca/Hotel-Search?startDate=26%2F04%2F2026&endDate=27%2F04%2F2026&selected=694639&PinnedHotelID=694639&HadPinnedHotel=true®ionId=601609) ![Hampton Inn & Suites North Conway](https://images.trvl-media.com/lodging/2000000/1510000/1507300/1507209/w3840h3044x0y3-8a2d4008_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hampton Inn & Suites North Conway 1788 White Mountain Hwy North Conway NH Fully refundableReserve now, pay when you stay CA $124 CA $135 total Apr 15 - Apr 16 includes taxes & fees 8.6/10 Excellent! (1,000 reviews) It was my first time staying at a hotel as an adult, this was for my 21rst birthday. The staff was incredibly friendly and welcoming. Reviewed on Mar 31, 2026 [](https://expedia.ca/Hotel-Search?startDate=15%2F04%2F2026&endDate=16%2F04%2F2026&selected=1507209&PinnedHotelID=1507209&HadPinnedHotel=true®ionId=601609) [See all 2,535 properties in Madison](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=02%2F04%2F2026&endDate=03%2F04%2F2026®ionId=601609) 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. ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations [](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations [](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Family Vacations [](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Vacations [](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Vacations [](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Vacations [](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Vacations [](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ## 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. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app