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 2,214 per night from Aug 2 to Aug 3
AEDĀ 2,214
AEDĀ 2,546 total
2 Aug - 3 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
Motel 6 New Haven - Branford, CT

Motel 6 New Haven - Branford, CT

2 out of 5
320 E Main St Branford CT
Fully refundable
The price is AEDĀ 232 per night from Aug 3 to Aug 4
AEDĀ 232
AEDĀ 271 total
3 Aug - 4 Aug
includes taxes & fees
7.2/10 Good! (1,013 reviews)
"Smelled in hallway and in the room like old cigarettes. No fridge in room. Needs updating."

Reviewed on 20 July 2026

Motel 6 New Haven - Branford, CT
Holiday Inn Express Southington by IHG

Holiday Inn Express Southington by IHG

2.5 out of 5
120 Laning St Southington CT
Fully refundable
The price is AEDĀ 346 per night from Aug 9 to Aug 10
AEDĀ 346
AEDĀ 398 total
9 Aug - 10 Aug
includes taxes & fees
8.8/10 Excellent! (1,375 reviews)
"Good service and excellent hotel"

Reviewed on 19 July 2026

Holiday Inn Express Southington by IHG
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.