Madison Vacations
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Madison Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Old Orchard Beach Inn
$739
per person
Sep 21 - Sep 26
found 1 day ago
Roundtrip non-stop flight included
Tulsa (TUL) to Portland (PWM)
Stay at this B&B in Old Orchard Beach. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Palace Playland and Old Orchard Beach are located nearby.
This review has been rejected several times, perhaps because it was too negative. Of the three properties I booked for this trip on different platforms, Old Orchard Beach Inn was the most disappointing. The room and bathroom needed a complete refresh. The furniture was old (not antique, poor reproductions and broken down). The bathroom was small and very dated. There was only one very small window and the room was dark. The lighting was terrible. Location was good. I only interacted with one staff person, who booked me in. The breakfast was acceptable--eggs, sausage and potatoes kept warm on a flame, and a fairly good variety of other breakfast foods. The breakfast is served two doors away, a short walk but it was pouring rain that morning. Parking was fine. This property was below my expectations for Hotels.com, compared with other properties I have booked on your platform. My rating for this property is significantly lower than the one on your website.
Reviewed on Aug 9, 2026
Portland Harbor Hotel
Downtown Portland
$1,453
per person
Sep 21 - Sep 26
found 1 day ago
Roundtrip non-stop flight included
Tulsa (TUL) to Portland (PWM)
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, 3 coffee shops/cafes, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Cross Insurance Arena and Casco Bay Lines Ferry Terminal are located nearby.
We had a shower that leaked all the way out to the foyer. We called and reported it. They sent a repair person. They caulked around the edge which helped but didn’t fix the whole problem. It still leaked, just not as bad. No one followed up to see if it was fixed. They have a pantry on each floor with fruit infused water snacks, fresh fruit, cookies, canned sparkling water and ice for free. But it was mostly depleted most of the time we were there. There was a sign advertising live music at the front of the hotel. But when we asked where it was, the hotel attendant said they were not having live music after all. No one went to take the sign down. It was still there the next day. We checked out. Hope the musician showed up that night.
Reviewed on Aug 7, 2026
The Docent's Collection at 121 Middle Street
Downtown Portland
$1,675
per person
Sep 21 - Sep 26
found 1 day ago
Roundtrip non-stop flight included
Tulsa (TUL) to Portland (PWM)
Stay at this hotel in Portland. Enjoy free WiFi, parking (surcharge), and premium TV channels. Popular attractions Casco Bay Lines Ferry Terminal and Cross Insurance Arena are located nearby.
Fantastic and always accommodating staff!
Reviewed on Aug 7, 2026
The Weldon Hotel
Downtown Portland
$2,077
per person
Sep 21 - Sep 26
found 1 day ago
Roundtrip non-stop flight included
Tulsa (TUL) to Portland (PWM)
Book a stay at this luxury aparthotel in Portland. Enjoy free WiFi, a 24-hour fitness center, and parking (surcharge). Popular attractions Cross Insurance Arena and State Theatre are located nearby.
The rooms were clean and spacious. The location was very convenient to the Old port. Parking was right across the street. The only drawback was a mechanical noise that we believe originated from the building next door. This noise made it sometimes difficult to sleep. Having a kitchen and laundry were helpful.
Reviewed on Aug 4, 2026
The Docent's Collection at 178 Middle Street
Downtown Portland
$2,282
per person
Sep 21 - Sep 26
found 1 day ago
Roundtrip non-stop flight included
Tulsa (TUL) to Portland (PWM)
Stay at this hotel in Portland. Enjoy free WiFi, parking (surcharge), and a 24-hour front desk. Popular attractions Cross Insurance Arena and Casco Bay Lines Ferry Terminal are located nearby.
Evalina Hotel
Downtown Portland
$2,289
per person
Sep 21 - Sep 26
found 1 day ago
Roundtrip non-stop flight included
Tulsa (TUL) to Portland (PWM)
Stay at this aparthotel in Portland. Enjoy free WiFi, parking (surcharge), and in-room washers/dryers. Popular attractions Maine Mall and Cross Insurance Arena are located nearby.
It was our first time visiting Portland, and the Evalina exceeded our expectations. The location is perfect, right on Commercial Street, with plenty of restaurants and shops nearby. The ferry and cruise ports are also just a 5–10 minute walk away, making it easy to visit the different islands.
The suite was comfortable and thoughtfully equipped with everything we could need, including an umbrella for rainy days, coffee and a French press, tea, a washer and dryer, and so much more. Communication was excellent throughout our stay as well.
We truly enjoyed our visit, and the next time we’re in Portland, the Evalina will be our first choice!
Reviewed on Aug 8, 2026
Madison Vacation Packages
Trying to save money and time on your upcoming vacation to Madison? Well, AARP Travel Center Powered by Expedia® is here to help. We can assist you with hotel bookings, flights, car rentals and more. You can get almost everything you need here to make your trip to Madison perfect. Our Travel Center is a one-stop shop where you can put together the best Madison vacation package for you and your family. We have an amazing selection of flights and lodgings, as well as local activities to choose from.
Hotels in Madison
With 2614 hotels and resorts in Madison to choose from, you are bound to find one that meets your needs.
We have great deals on everything from luxury hotels that check off all the vacation must-haves to inexpensive accommodations which are great for those on a budget. You can search our vast catalog of options and choose the accommodation that is best for you. With AARP Travel Center's Madison hotel packages, you not only get a great rate on your flight, but also a fantastic place to stay.
Things to do in Madison
Madison is the ideal place when you have to a break from it all. With only around 2,518 people in the city, this quaint town is great for a quite vacation.
If you are looking for more, then head over to our "Things to Do" tab for more inspiration or to reserve an activity in Madison.
Package Your Madison Vacation and Save
With so much going on in Madison, you'll be wanting to plan your outings, not devoting time to finding the hotel with the lowest rate. The AARP Travel Center Powered by Expedia® allows you to easily get all you wish for, and save money on your vacation. You can plan your whole trip, including things to do in Madison from just one site. The hardest packing you'll have to do is for your suitcase. Bundle today and save!
Top Hotel Deals
Purity Spring Resort
1251 Eaton Rd Madison NH
Book a stay at this ski hotel in Madison. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff in our reviews. Popular attractions ...
North Conway Grand Hotel
72 Common Court North Conway NH
Book a stay at this family-friendly hotel in North Conway. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the pool and the helpful ...
North Conway Mountain Inn
2114 White Mountain Highway North Conway NH
Book a stay at this golf motel in North Conway. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the helpful staff and the clean rooms ...
Swiss Chalets Village Inn
457 Intervale Resort Loop Intervale NH
Book a stay at this golf hotel in Intervale. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our ...
Golden Gables Inn Dazzler Select by Wyndham
1814 White Mountain Hwy North Conway NH
Stay at this motel in North Conway. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. ...
School House Inn
2152 White Mountain Highway North Conway NH
Stay at this hotel in North Conway. Enjoy free WiFi, free parking, and concierge services. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Nordic Village Resort
Route 16 Jackson NH
Book a stay at this family-friendly aparthotel in Jackson. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. ...
Eagle Mountain House & Golf Club
179 Carter Notch Rd Jackson NH
Book a stay at this historic hotel in Jackson. Enjoy an outdoor pool, a golf course, and breakfast (surcharge). Our guests praise the helpful staff and the property ...
Christmas Farm Inn and Spa
3 Blitzen Way Jackson NH
Book a stay at this spa hotel in Jackson. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our ...
The Green Granite North Conway, an Ascend Collection Hotel
1515 White Mountain Hwy North Conway NH
Book a stay at this family-friendly hotel in North Conway. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in ...
The Lodge At Jackson Village
153 Route 16 Jackson NH
Book a stay at this beach hotel in Jackson. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. ...
The White Mountain Hotel & Resort
87 Fairway Drive North Conway NH
Book a stay at this spa resort in North Conway. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the property condition ...
Cambria Hotel North Conway
1858 White Mountain Highway North Conway NH
Book a stay at this business-friendly hotel in North Conway. Enjoy free WiFi, free parking, and breakfast (surcharge). Popular attractions Settlers' Green Outlet ...
White Mountain Cottages
2406 White Mountain Hwy North Conway NH
Stay at this cabin in North Conway. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Story Land and Conway Scenic Railway are located ...
Home2 Suites by Hilton North Conway
1439 White Mountain Hwy North Conway NH
Book a stay at this business-friendly hotel in North Conway. Enjoy free breakfast, free parking, and a 24-hour fitness center. Our guests praise the breakfast ...
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.
Top Flight Deals
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Mon, Aug 31 - Tue, Sep 1
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$202
Roundtrip
found 1 day ago
Thu, Oct 8 - Fri, Oct 16
EWR
Newark Liberty Intl. Airport
PWM
Portland Intl. Jetport
$237
Roundtrip
found 6 days ago
Wed, Aug 26 - Wed, Sep 9
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
$247
Roundtrip
found 1 day ago
Mon, Aug 31 - Tue, Sep 1
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$248
Roundtrip
found 1 day ago
Mon, Aug 31 - Tue, Sep 1
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$267
Roundtrip
found 1 day ago
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