Madison Vacation Packages

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Your Madison Vacation

Reserve a Madison vacation package that includes everything you need and no unnecessary extras. Great for walking, hiking and views, think about basing yourself in the neighborhood of Essex Village. Hammonasset Beach State Park, Hammonasset Beach and Meigs Point Nature Center are just a few of the many sights worth checking out during your trip to Madison. That dream Madison vacation is a few clicks away. Explore airfares, hotels and more on Expedia for a trip that's tailored just for you.

Top Madison Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Hampton Inn Milford

Hampton Inn Milford

2.5 out of 5
per person
Sep 7 - Sep 10
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to New Haven (HVN)
8/10 Very Good! (1,002 reviews)
4 nights stay no changes of biddings and refill of toiletries

Reviewed on Aug. 4, 2025

Omni New Haven Hotel at Yale

Omni New Haven Hotel at Yale

4 out of 5
Downtown New Haven
per person
Sep 7 - Sep 10
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to New Haven (HVN)
8.4/10 Very Good! (1,011 reviews)
Overall was a decent stay. Staff was very friendly, but the hotel is very dated and the location is a tad sketchy.

Reviewed on Aug. 7, 2025

Graduate by Hilton New Haven

Graduate by Hilton New Haven

4 out of 5
Downtown New Haven
per person
Sep 7 - Sep 10
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to New Haven (HVN)
9.2/10 Wonderful! (851 reviews)
Scenic design of property and great location

Reviewed on Aug. 8, 2025

Cambria Hotel New Haven University Area

Cambria Hotel New Haven University Area

3 out of 5
West River
per person
Sep 7 - Sep 10
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to New Haven (HVN)
8.8/10 Excellent! (838 reviews)
Clean and quiet. Checked in late and checked out early. So didn’t really have the time to explore

Reviewed on Aug. 6, 2025

Hilton Garden Inn Milford

Hilton Garden Inn Milford

3 out of 5
per person
Sep 7 - Sep 10
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to New Haven (HVN)
8.2/10 Very Good! (1,001 reviews)
great trip and friendly staff

Reviewed on Jul. 28, 2025

Ready to book your vacation to Madison?

 

Choose your dates

Madison Hotel Deals

Madison Beach Hotel

Madison Beach Hotel

4 out of 5
94 West Wharf Road, Madison, CT
The price is CA $587 per night from Sep 7 to Sep 8
CA $587
CA $676 total
Sep 7 - Sep 8
includes taxes & fees
9.4/10 Exceptional! (305 reviews)
"Everything was wonderful! Everyone was extremely friendly and helpful! The room was comfortable with a beautiful view from the balcony. I would highly recommend!!"

Reviewed on Aug. 1, 2025

Madison Beach Hotel
Cambria Hotel New Haven University Area

Cambria Hotel New Haven University Area

3 out of 5
20 Dwight Street, New Haven, CT
Fully refundableReserve now, pay when you stay
The price is CA $186 per night from Aug 24 to Aug 25
CA $186
CA $213 total
Aug 24 - Aug 25
includes taxes & fees
8.6/10 Excellent! (838 reviews)
"Very near Yale university. The hotel is very clean and the hotel staff were kind and helpful. I got a work out in their nice fitness room. I enjoyed my stay before making my self into NYC."

Reviewed on Aug. 2, 2025

Cambria Hotel New Haven University Area
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 CA $144 per night from Aug 12 to Aug 13
CA $144
CA $165 total
Aug 12 - Aug 13
includes taxes & fees
7.8/10 Good! (1,250 reviews)
"Clean and efficient. Family friendly."

Reviewed on Aug. 5, 2025

Best Western Executive Hotel Of New Haven - West Haven
See all 1,914 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.
All Inclusive Vacations
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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 from CA $591 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 — ideal for budget-conscious travellers.
How many days is enough for Madison?
When planning your Madison vacation, a few days will be enough to see the top spots. Make sure to check out Guilford Art Centre — it's one of the top sights in this destination. If you're after more activities, think about basing yourself here and venturing off on some tours from Madison.
Is it worth booking a vacation package to Madison?
Whether you're planning to check out attractions like Hammonasset Beach State Park and Scranton Memorial Library, or eager to experience its top-notch cafes and dining, a Madison vacation will leave you with lasting memories. Book your getaway with Expedia and discover why Madison is such a good vacation destination.
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, favourite 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.

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