Madison Vacations from $537
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The Latest Madison Vacation Packages
- Cold Spring Plymouth Resort
Aug 26 - Aug 30Cold Spring Plymouth Resort + Flight
Ashland4 nights3.5 star property9.2/10 - Wonderful (228 reviews)"All mattresses seemed very old and springy in all rooms. Shower and toilet crammed into small room, could not sit comfortably when using rest room and I'm only 5'9 215 lbs. Everything else was good. Kitchen was well stocked with pans, plates, small appliances etc. First time staying at a place like this. Will just use a hotel next time so we can get fresh linens etc."Reviewed July 13, 2026Roundtrip • New York (NYC) - Manchester (MHT)JFK - BOS • Nonstop BOS - JFK • Nonstop - The Centennial
Sep 24 - Sep 30The Centennial + Flight
Concord6 nights4.0 star property8.8/10 - Excellent (1,000 reviews)"The room was clean and comfortable but there was a window ac unit and no shade on the window. Closing the curtains for privacy meant blocking the ac. The room also lacked a full length mirror and had limited bathroom vanity space. I did like the laminate floors, the room was a nice size and the bed was comfy"Reviewed July 5, 2026Roundtrip • Chicago (CHI) - Manchester (MHT)ORD - BOS • 1 stop BOS - RFD • 1 stop - Ogunquit River Inn & Suites
Sep 4 - Sep 7Ogunquit River Inn & Suites + Flight
Moody3 nights3.0 star property9.0/10 - Wonderful (1,003 reviews)Roundtrip • Chicago (CHI) - Portland (PWM)ORD - PWM • Nonstop PWM - ORD • Nonstop - Eastern Slope Inn Resort
Aug 19 - Aug 23Eastern Slope Inn Resort + Flight
North Conway Village4 nights3.0 star property8.8/10 - Excellent (470 reviews)"Love this classic well maintained hotel."Reviewed July 9, 2026Roundtrip • New York (NYC) - Manchester (MHT)JFK - BOS • Nonstop BOS - JFK • Nonstop - Evalina Hotel
Sep 25 - Sep 28Evalina Hotel + Flight
Downtown Portland3 nights2.5 star property10/10 - Exceptional (5 reviews)"I want to give this a 5 plus! Gorgeous apartment with new and reclaimed touches. It has everything you need and more to feel right at home. The location could not be better. Steps to the best dining and shopping. Communication was thoughtful, easy, and fast. Definitely will return!"Reviewed June 19, 2026Roundtrip • Chicago (CHI) - Portland (PWM)ORD - PWM • Nonstop PWM - ORD • 1 stop
Where to stay in Madison
Eidelweiss Village
While there might not be top attractions in Eidelweiss Village, you can explore the larger area and discover places like Madison Boulder Natural Area and Madison Boulder.
Discover the most popular places to visit in Madison
Madison Hotel Deals
Frequently Asked Questions
How much does a Madison vacation package cost?
You'll find cheap prices from $537 on Expedia for your Madison getaway. However, a range of factors like the season, length of stay and your choice of hotel will influence how much your vacation to Madison costs.
What are the cheapest months to go to Madison?
If you're looking to book a cheap Madison vacation package, consider planning a trip in February, May and November. You'll typically find better prices on flights and hotels during these months — ideal for a budget-friendly getaway.
How many days is enough for Madison?
With a well-planned itinerary, you can easily visit the most popular Madison attractions in a handful of days. But if you want to discover hidden spots or go on day trips, consider booking your Madison vacation for longer.
How to find the best Madison package deals?
Use Expedia's handy filters to find some terrific Madison package deals. When you begin your search, just set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your adventure for midweek, or browse for Madison package deals in the off-season. Switch up your travel dates and you may score even bigger discounts. As a rule of thumb, it's typically best to lock in your vacation package well in advance.
Is it cheaper to book a 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 enjoy significant savings. You'll generally score a better deal than booking each component individually. And you'll still get the freedom to create a customized Madison vacation by choosing your favorite type of stay, airline and car class.
When to book a vacation package to Madison?
If you have your Madison vacation dates confirmed, book as soon as you can to bag some terrific deals. With Expedia, you can generally reserve some flights up to a year in advance. Prefer spontaneous getaways? Our last-minute deals are perfect for impromptu escapes.
Does Expedia offer Book Now, Pay Later Madison vacation packages?
Jet off on your perfect escape to Madison with help from our Book Now, Pay Later vacations. No need to save like crazy or hold off until your next paycheck — we've joined forces with online lender Affirm to give you more flexibility and choice. Our vacation packages with payment plans allow you to split the cost over 3, 6 or 12 months. With no late payment fees or extra charges, it's a breeze to stay on budget and snap up cheap deals while they last.
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Things to do near Madison
Madison, New Hampshire, is perfect for outdoor enthusiasts and those seeking romantic getaways. You can hit the ski fields or enjoy a nearby ski resort for some winter fun. For a scenic experience, consider a Sunday drive or bike ride through the picturesque landscapes. Don’t forget to explore free attractions that offer excitement and charm, making your visit memorable.
Shopping
The nearest shopping options include the L. L. Bean Factory Store, only 6 miles away, perfect for outdoor gear. Settlers' Green Outlet Village and Northway Plaza Shopping Center are both 9 miles away, offering a variety of shops and a vibrant atmosphere. If you're up for a drive, you'll find even more options.
Recreation
Enjoy a round of golf at North Conway Country Club, where the scenic views enhance your game. For family fun, head to Pirate's Cove Adventure Mini Golf for a thrilling mini-golf experience. Finally, catch a live performance at Stone Mountain Arts Center for an entertaining evening.
Adventure
Experience the thrills at Kahuna Laguna, a vibrant waterpark located 10 miles from Madison, perfect for family fun. For winter sports, head to Cranmore Mountain Resort, 11 miles away, offering fantastic skiing opportunities. Don't miss Monkey Trunk Chocorua, an exciting arcade adventure zone just 4 miles from town.
Nightlife
Madison, New Hampshire, offers a relaxed nightlife with charming venues like The Snowvillage Inn, perfect for cozy dinners and drinks. For a lively atmosphere, visit local bars and pubs that often feature live music, creating a friendly setting to unwind and mingle with locals and fellow tourists.
Find the best attractions near Madison
Madison, New Hampshire, is a picturesque destination perfect for outdoor enthusiasts and romantic getaways. Visitors can explore beautiful lakes, historic railways, and scenic rivers, making it an ideal spot for adventure and nature lovers. Notable attractions include the local Madison Museum and various outdoor activities that promise stunning views and memorable experiences. Whether you're seeking tranquility or adventure, Madison offers a delightful escape in the heart of New England.
- Saco River: Experience the natural beauty of the Saco River, located a mere 6 miles from Madison. Enjoy picturesque scenery and a variety of outdoor activities like kayaking, fishing, and hiking along its banks, perfect for nature lovers seeking adventure.
- Conway Scenic Railway: Step back in time with the Conway Scenic Railway, situated 11 miles away. This historic train ride offers a unique cultural experience, showcasing the stunning landscapes of New Hampshire while immersing you in the rich history of rail travel.
- Ossipee Lake: Just 8 miles from Madison, Ossipee Lake is a beautiful destination for beach lovers. Enjoy scenic views, outdoor activities, and a romantic atmosphere, making it ideal for relaxation and creating unforgettable memories.
Best time to go to Madison
The best time to visit Madison is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are average and weather is mostly sunny with light rain.
Tips to save on your trip to Madison
- Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Madison.
- Consider traveling during the off-peak season (typically March to May) for more affordable package holidays to Madison.
- Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
- Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.