Madison Vacations

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Find the Best Madison Vacation Packages

Madison Hotel Deals

Madison Beach Hotel

Madison Beach Hotel

94 West Wharf Road Madison CT
NT$14,244
NT$16,380 total
Sep 21 - Sep 22
includes taxes & fees
Madison Beach Hotel
New Haven Hotel

New Haven Hotel

229 George Street New Haven CT
Fully refundableReserve now, pay when you stay
NT$4,129
NT$4,749 total
Sep 21 - Sep 22
includes taxes & fees
9.2/10 Wonderful! (2,315 reviews)
"The staff didn’t tell us the parking is at cost and charge us directly after we check out"

Reviewed on 2026/9/6

New Haven Hotel
Sound View Greenport

Sound View Greenport

58775 County Rd 48 Greenport NY
NT$9,255
NT$13,285 total
Sep 28 - Sep 29
includes taxes & fees
8.4/10 Very Good! (714 reviews)
"Amazing location; pool and nighttime tavern on weeekends are great but beware room accommodations- doors often fail to open the right way (locked out of room), room was fly invested at night. The suites in the second building are well maintained but the standard rooms in first building (100 levels) ..."

Reviewed on 2026/9/5

Sound View Greenport
See all 2,003 properties in Madison
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

A rural landscape with a large fallen tree in the foreground, fields, and a forest in the background.
Photo by Shannon Willitts

Hammonasset Beach State Park

8.8/10 (137 reviews)
Connecticut's largest shoreline park features two miles of sandy beach along Long Island Sound. Explore hiking trails or visit the Meigs Point Nature Center for interactive exhibits about local ecosystems.
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A stone pier extending into calm waters at sunset with a person standing at the end.

Hammonasset Beach

9.4/10 (14 reviews)
Connecticut's largest shoreline park offers two miles of sandy beaches along the Long Island Sound. Explore diverse ecosystems on nature trails or visit the Meigs Point Nature Center for wildlife exhibits.
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North Madison Shopping Center

8.8/10 (10 reviews)
This local retail hub offers convenient shopping with a variety of stores and services for everyday needs. Browse through grocery, clothing, and dining options while enjoying the relaxed small-town atmosphere.
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Allis-Bushnell House and Museum

8.0/10 (2 reviews)
Step into 1785 at this historic house museum showcasing local artifacts and maritime heritage. Explore period rooms with working looms, spinning wheels, and a charming colonial herb garden.
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East Wharf Beach Park

Why not spend a lazy afternoon at East Wharf Beach Park during your trip to Madison?
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RJ Julia Booksellers

9.6/10 (12 reviews)
This beloved independent bookstore hosts over 300 author events annually in its charming two-story space. Browse the thoughtfully curated selection, then relax with your new book at the cozy in-store café.
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Scranton Memorial Library

8.0/10 (3 reviews)
The E.C. Scranton Memorial Library has served Madison since 1901 with over 100,000 volumes. Browse their extensive collection or attend one of their frequent author talks and cultural workshops.
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Madison Green Historic District

You can learn about the history of Madison when you stop by Madison Green Historic District.
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Frequently asked questions

How much does a Madison vacation package cost?
You can grab a vacation package to this top destination on Expedia. However, how much your vacation to Madison costs will depend on the season, hotel choice and length of stay.
What are the cheapest months to go to Madison?
You can usually find lower prices and better availability in January, February and November. Take a look at our cheap Madison vacation packages and you could score some great off-season discounts.
How many days is enough for Madison?
For your Madison vacation, a few days will be enough to see all the highlights. Be sure to stop by Meigs Point Nature Center — it's one of the major attractions in this destination. If you're looking for more adventure, consider basing yourself here and setting off on some tours from Madison.
Is it worth booking a vacation package to Madison?
During your Madison vacation, you can count on experiencing some top-notch cafes and dining. Leave enough room in your itinerary to visit major sights like Hammonasset Beach State Park and Scranton Memorial Library.
How to find the best Madison package deals?
Use Expedia's filters to find some of the best Madison package deals. When you start your search, simply set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your break for midweek, or look for Madison package deals in the off-peak season. Play around with your travel dates and you may score even bigger discounts. As a rule of thumb, it's usually best to lock in your vacation package as early as possible.
Is it cheaper to book a Madison vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your flight, hotel and car rental into one great-value price and enjoy significant savings. You'll typically snag a better deal than booking each component individually. And you'll still get the freedom to create a personalized Madison vacation by choosing your favorite accommodation type, airline and car class.
When to book a vacation package to Madison?
Score incredible bargains by reserving your flights in advance with Expedia. If spontaneity is more your style, snap up one of our last-minute deals for a spur-of-the-moment Madison getaway.
How to plan a trip to Madison?
  1. Choose when to go: Check your diary and get your bags packed. Your favorite time of year and the activities available will also help you decide when to visit Madison.
  2. Budget wisely: On top of the price of your hotel, you'll need to factor in other expenses. These include flights, transportation and food. Also, put aside some extra funds for unexpected expenses that may arise during your trip to Madison.
  3. Determine how many days away: Start by compiling a list of the attractions you'd like to get to in Madison. Then, estimate how long you'll need at each, along with any travel time.
  4. Bundle your hotel and flights: Epic destination, check. Length of stay, check. All that's left is to choose a Madison vacation package that brings all your bookings together.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.