Madison Vacations

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  • Better together

    Save up to AEDĀ 5,000 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

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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 AEDĀ 2,357 per night from Aug 9 to Aug 10
AEDĀ 2,357
AEDĀ 2,710 total
9 Aug - 10 Aug
includes taxes & fees
9.4/10 Exceptional! (376 reviews)
"Loves having waiter service directly on the beach"

Reviewed on 2 July 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 AEDĀ 475 per night from Aug 9 to Aug 10
AEDĀ 475
AEDĀ 546 total
9 Aug - 10 Aug
includes taxes & fees
9.2/10 Wonderful! (2,219 reviews)
"Best place ever"

Reviewed on 18 July 2026

New Haven Hotel
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
1430 Boston Post Rd Old Saybrook CT
Fully refundable
The price is AEDĀ 336 per night from Jul 19 to Jul 20
AEDĀ 336
AEDĀ 387 total
19 Jul - 20 Jul
includes taxes & fees
8/10 Very Good! (1,003 reviews)
"Hotel is outdated but clean and well kept, service was great. Great for a one or two night stay. I recommend it for families and especially if traveling with a pet."

Reviewed on 18 July 2026

Pier Blue Inn Old Saybrook - Essex
See all 1,993 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 pick up a vacation package to this popular destination on Expedia. But how much your vacation to Madison costs will depend on factors like the length of stay, hotel choice and season.
What are the cheapest months to go to Madison?
If you're looking to score a cheap Madison vacation package, consider visiting in January, February and November. You're likely to find lower rates on hotels and flights during these months ā€” ideal for budget-conscious travelers.
How to find the best Madison package deals?
Start your search for a Madison package deal by entering your preferred trip dates and destination under our "Packages" tab. Then add some filters, like "Property type" and "Guest rating," to fine-tune the results to your exact needs. You can also sort by "Package discount" and browse offers that come with huge savings. If you don't find the perfect Madison package deal right away, just tweak your dates and search again. Remember that deals are only available for a limited time, so book early and get your Madison getaway off to a flying start.
Is it cheaper to book a Madison vacation as a package?
You can enjoy significant savings on your Madison break by booking a tailored vacation package. Check the "Package" heading, then enter your destination and travel dates to view the best hotel prices and airfares. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Madison?
If you've got your Madison travel dates finalized, book early to score some fantastic deals. With Expedia, you can generally reserve some flights up to a year in advance. Prefer spur-of-the-moment getaways? Our last-minute deals are perfect for quick escapes.
How to plan a trip to Madison?

  1. Choose the right time to travel: Your schedule, favorite season and the type of weather you enjoy can all impact your decision on when to visit Madison.
  2. Plan your budget wisely: As well as the price of your stay, you'll need to consider other expenses. These include flights, transportation and food. Also, set aside some extra funds for unexpected costs that may crop up during your trip to Madison.
  3. Decide your trip length: Think about how long you want to spend exploring Madison. Plan your days so you can get to all the activities and attractions you're interested in at a comfortable pace.
  4. Bundle your bookings: With your travel dates in order, you can combine your car rental, flights, hotels and more into a personalized Madison vacation package.