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.
Ogunquit River Inn & Suites
Moody
CA $1,539
per person
Oct 8 - Oct 12
found 4 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9/10 Wonderful! (1,017 reviews)
Check in was quick and the front desk attendant was very pleasant. We used the pool which was great, however, it needed to be skimmed. A ton of grass, hair and debris floating in the pool.
Housekeeping visited our room which was great. They replenished towels and made our bed. A pleasant surprise as most hotels/motels do not offer this service daily.
They also offer a continental breakfast and tea and coffee all day.
The room was updated and clean with a second floor balcony overlooking the river.
We asked for a late check out and for $30 we were able to check out two hours later which was so helpful.
A great place to stay which was very reasonably priced. We will definitely be back before winter.
Reviewed on Aug 12, 2026
The Docent's Collection at 121 Middle Street
Downtown Portland
CA $2,697
per person
Sep 24 - Sep 28
found 5 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Portland (PWM)
9.6/10 Exceptional! (367 reviews)
We had no idea how fabulous our stay was going to be! The loft space was beautifully appointed and so inviting. Full kitchen had amenities you didn't even know you wanted (frozen marble wine bottle holder, deluxe swivel Scrabble game and art books, anyone?). The whole place left you feeling spa-like and city-savvy at the same time. Hannah and Anna were the staff who helped us--they were responsive, courteous, and answered all of our questions before and during our stay. Check-in was super easy. The location was perfect--right in the heart of the Old Port, so we walked to everything. Don't miss this fabulous place!
Reviewed on Aug 12, 2026
Inn By The Sea
CA $2,644
per person
Sep 24 - Sep 28
found 5 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Portland (PWM)
9.6/10 Exceptional! (327 reviews)
(+)
Location
Dog Friendly
Food
Parking
Everything you would expect from a luxury hotel - it is pricy.
Nothing negative.
Reviewed on Aug 2, 2026
Ready to book your vacation to Madison?
Madison Hotel Deals
Purity Spring Resort
1251 Eaton Rd Madison NH
Fully refundableReserve now, pay when you stay
CA $144
CA $194 total
Aug 16 - Aug 17
includes taxes & fees
8.8/10 Excellent! (217 reviews)
"The rooms may look dated but are clean with comfortable beds. The available activities are where it’s at — we played tennis, shuffleboard, volleyball, badminton, kayaked, and even swam. All the equipment is in great shape. We can’t wait to return."
Reviewed on Aug 8, 2026
North Conway Grand Hotel
72 Common Court North Conway NH
Fully refundableReserve now, pay when you stay
CA $168
CA $216 total
Sep 2 - Sep 3
includes taxes & fees
8.6/10 Excellent! (1,209 reviews)
"clean and convenient location. This hotel tends to cater to families, many childeren about the common areas."
Reviewed on Aug 13, 2026
North Conway Mountain Inn
2114 White Mountain Highway North Conway NH
Fully refundableReserve now, pay when you stay
CA $124
CA $135 total
Aug 16 - Aug 17
includes taxes & fees
8.8/10 Excellent! (1,262 reviews)
"Traditional hotel room with all the basics. With amazing views and great hospitality from the staff. We would definitely go back goback."
Reviewed on Aug 12, 2026
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.
Stay near popular Madison attractions
beach near Davis Pond
Why not spend a lazy afternoon at beach near Davis Pond during your trip to Madison? Amble around the area's lakeside or visit its shops.
beach near Lyman Town Forest
Why not spend a lazy afternoon at beach near Lyman Town Forest during your trip to Madison? Amble around the area's lakeside or visit its shops.
beach near Madison Boulder Natural Area
Why not spend a lazy afternoon at beach near Madison Boulder Natural Area during your trip to Madison? Amble around the area's lakeside or visit its shops.
Frequently asked questions
How much does a Madison vacation package cost?
You'll find cheap prices from CA $1,198 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?
- 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.
- 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.
- 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.
- 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.
