Madison Vacations

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Find the Best Madison Vacation Packages

Madison Hotel Deals

Madison Beach Hotel

Madison Beach Hotel

4 out of 5
94 West Wharf Road Madison CT
The price is ￥101,934 per night from Jul 27 to Jul 28
￥101,934
￥117,225 total
Jul 27 - Jul 28
includes taxes & fees
9.4/10 Exceptional! (376 reviews)
"Loves having waiter service directly on the beach"

Reviewed on Jul 2, 2026

Madison Beach Hotel
New Haven Hotel

New Haven Hotel

3.5 out of 5
229 George Street New Haven CT
Fully refundableReserve now, pay when you stay
The price is ￥19,077 per night from Jul 26 to Jul 27
￥19,077
￥21,939 total
Jul 26 - Jul 27
includes taxes & fees
9.2/10 Wonderful! (2,195 reviews)
"Easy check-in and helpful staff. Only there over night as family member in Yale Hospital. Paring easy as was check out. Needs more charging ports."

Reviewed on Jul 3, 2026

New Haven Hotel
Best Western Executive Hotel Of New Haven - West Haven

Best Western Executive Hotel Of New Haven - West Haven

2.5 out of 5
490 Saw Mill Rd West Haven CT
Fully refundableReserve now, pay when you stay
The price is ￥16,642 per night from Jul 20 to Jul 21
￥16,642
￥19,138 total
Jul 20 - Jul 21
includes taxes & fees
8/10 Very Good! (1,696 reviews)
"The room was clean and fresh the workers was very kind I really loved it I wish they would give me some good comps thank you"

Reviewed on Jul 3, 2026

Best Western Executive Hotel Of New Haven - West Haven
See all 1,992 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
Open 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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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.

Explore a world of travel with Expedia

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