Madison Holidays

Photo by Shannon Willitts
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    Better together

    Save up to S$134 when you book a flight and hotel together*
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    Find the right fit

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

    Plan, book, and manage your trip all in one place

Top hotels in Madison

Madison Beach Hotel
Madison Beach Hotel
4 out of 5
94 West Wharf Road, Madison, CT
The price is S$662 per night from 21 Jul to 22 Jul
S$662
21 Jul - 22 Jul
includes taxes & fees
9.4/10 Exceptional! (298 reviews)
"Such a wonderful resort for a relaxation vacation. Just about a 1 1/2 easy drive down Route 95 from Providence, RI. The property is in great condition. Our room was spacious. There is easy access to hotel dining and other local restaurants. Nice walkable neighborhood. The private beach and beach ..."

Reviewed on 7 Jul, 2025

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 S$214 per night from 20 Jul to 21 Jul
S$214
20 Jul - 21 Jul
includes taxes & fees
8.8/10 Excellent! (1,638 reviews)
"Parking and within walking distance to restaurants and business destination."

Reviewed on 7 Jul, 2025

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 S$141 per night from 20 Jul to 21 Jul
S$141
20 Jul - 21 Jul
includes taxes & fees
7.6/10 Good! (1,180 reviews)
"Good stay, the rooms were not as clean as I’m used to but service was very accommodating"

Reviewed on 7 Jul, 2025

Best Western Executive Hotel Of New Haven - West Haven
See all 1,916 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.

Frequently asked questions

How much does a Madison holiday package cost?
You can grab a holiday package to this top destination on Expedia. However, how much your holiday 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 holiday packages and you could score some great off-season discounts.
How many days is enough for Madison?
For your Madison holiday, a few days will be enough to see all the highlights. Be sure to stop by Meigs Point Nature Centre --- 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 holiday package to Madison?
During your Madison holiday, 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 holiday package as early as possible.
Is it cheaper to book a Madison holiday as a package?
Expedia holiday 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 personalised Madison holiday by choosing your favourite accommodation type, airline and car class.
When to book a holiday 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 favourite 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 holiday package that brings all your bookings together.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.