East Madison Vacations from $448
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The Latest East Madison Vacation Packages
- Ogunquit River Inn & Suites
Sep 18 - Sep 20Ogunquit River Inn & Suites + Flight
Moody2 nights3.0 star property9.0/10 - Wonderful (1,017 reviews)Roundtrip • New York (EWR) - Portland (PWM)EWR - BOS • Nonstop BOS - EWR • Nonstop$608$448found 1 day agoper traveler - AWOL Kennebunkport
Sep 4 - Sep 9AWOL Kennebunkport + Flight
Kennebunkport5 nights3.0 star property9.4/10 - Exceptional (250 reviews)"Wonderful historic property updated with in-house suites & cabin-style lodgings. Adequate parking. Room was comfortable, new bathrooms & nice breakfast area. The breakfast itself was TDF!! The neighborhood is authentic. Walkable to downtown. Highly recommend."Reviewed July 20, 2026Roundtrip • Dallas (DFW) - Portland (PWM)DFW - PWM • Nonstop PWM - DFW • Nonstop - Evalina Hotel
Oct 11 - Oct 16Evalina Hotel + Flight
Downtown Portland5 nights2.5 star property10/10 - Exceptional (5 reviews)"It was a spacious, clean, well thought out space with all the expected amenities. The location is ideal, and the hotel is truly a treasure."Reviewed June 28, 2026Roundtrip • Dallas (DAL) - Portland (PWM)DAL - PWM • 1 stop PWM - DAL • 1 stop - The Weldon Hotel
Oct 11 - Oct 16The Weldon Hotel + Flight
Downtown Portland5 nights4.5 star property9.8/10 - Exceptional (105 reviews)"Highly recommended. Pricey but well worth it. The unit was clean, spacious, and exceptionally well appointed."Reviewed July 26, 2026Roundtrip • Dallas (DAL) - Portland (PWM)DAL - PWM • 1 stop PWM - DAL • 1 stop - The Meadowmere Resort
Sep 12 - Sep 16The Meadowmere Resort + Flight
Ogunquit4 nights2.5 star property8.6/10 - Excellent (1,001 reviews)"I requested a room accessible for my 90 year old mother with a walker. We got that. I asked the front desk woman if there was another entrance to the pool because the one at the entrance had many stairs. She said no. Another traveler in the lobby told me there is one around the back. The staff member said they never took her around the property and trained her when the woman said that. They play music all day and night until 10:30pm outside my room by a speaker. I requested it be turned off and..."Reviewed July 22, 2026Roundtrip • Dallas (DFW) - Portland (PWM)DFW - PWM • Nonstop PWM - DAL • 1 stop$1,141$842found 1 hour agoper traveler
East Madison Hotel Deals
Home2 Suites by Hilton North Conway
Home2 Suites by Hilton North Conway
Comfort Inn & Suites North Conway
Comfort Inn & Suites North Conway
Residence Inn by Marriott, North Conway
Residence Inn by Marriott, North Conway
Hampton Inn & Suites North Conway
Hampton Inn & Suites North ConwayFrequently Asked Questions
How much does an East Madison vacation package cost?
You'll find cheap prices from $448 on Expedia for your East Madison escape. However, a range of factors like the season, choice of hotel and length of stay will determine how much your vacation to East Madison costs.
What are the cheapest months to go to East Madison?
February, May and November are the best times to look for cheap East Madison vacation packages. Opting to travel in quieter months means you can usually find better prices on hotels and flights.
How many days is enough for East Madison?
With a well-organized schedule, you can easily hit the top East Madison sights in a few days. But if you prefer to discover lesser-known spots or go on day tours, consider booking your East Madison vacation for longer.
How to find the best East Madison package deals?
Finding a cheap East Madison package deal is a cinch with Expedia. Once you've entered your trip dates and destination under our "Packages" tab, set your maximum budget, add a couple of filters and see what's available. You can personalize your search by "Area," "Amenities," "Property type" and more. Sort the results by "Price: low to high" to discover the most pocket-friendly East Madison package deals. Want a simple trick to get the biggest savings? Have some flexibility with your departure dates and consider traveling on a weekday, when prices are usually lower.
Is it cheaper to book an East Madison vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your car rental, flight and hotel into one great-value price and you could save hundreds of dollars. You'll typically land a better deal than booking each component separately. And you'll still get the flexibility to create a personalized East Madison vacation by choosing your favorite airline, accommodation type and car class.
When to book a vacation package to East Madison?
Secure incredible discounts by reserving your flights in advance with Expedia. If spontaneity is more your style, take advantage of our last-minute deals for an impromptu East Madison escape.
Does Expedia offer Book Now, Pay Later East Madison vacation packages?
Jet off on your perfect escape to East Madison with help from our Book Now, Pay Later vacations. There's no need to save up or wait until your next payday — we've joined forces with online lender Affirm to give you more flexibility with your finances. Our vacation packages with payment plans let you split the cost over 3, 6 or 12 months. With no hidden charges or late payment fees, it's easy to stay on budget and snap up travel deals before they disappear.