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.
Aderi Hotel Niantic

Aderi Hotel Niantic

2 out of 5
Price was CA $875, price is now CA $858 per person
CA $858
per person
Nov 14 - Nov 16
found 13 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to New Haven (HVN)
6.2/10 (673 reviews)
Front desk staff at check in was so polite and friendly!

Reviewed on Aug. 12, 2025

Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
Price was CA $2,558, price is now CA $1,643 per person
CA $1,643
per person
Oct 10 - Oct 13
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New Haven (HVN)
No reviews
Microtel Inn & Suites by Wyndham Uncasville Casino Area

Microtel Inn & Suites by Wyndham Uncasville Casino Area

2.5 out of 5
Price was CA $1,285, price is now CA $1,212 per person
CA $1,212
per person
Nov 14 - Nov 16
found 13 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to New Haven (HVN)
8.8/10 Excellent! (1,737 reviews)
Clean and close to casino

Reviewed on Aug. 24, 2025

Hyatt Place Uncasville - Casino Area

Hyatt Place Uncasville - Casino Area

3 out of 5
Price was CA $1,343, price is now CA $1,304 per person
CA $1,304
per person
Nov 14 - Nov 16
found 13 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to New Haven (HVN)
9.2/10 Wonderful! (2,537 reviews)
Very close to Moheagan Sun

Reviewed on Aug. 25, 2025

Fairfield by Marriott Inn & Suites Uncasville Mohegan Sun Area

Fairfield by Marriott Inn & Suites Uncasville Mohegan Sun Area

3 out of 5
Price was CA $1,335, price is now CA $1,335 per person
CA $1,335
per person
Nov 14 - Nov 16
found 13 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to New Haven (HVN)
9.2/10 Wonderful! (1,006 reviews)
Breakfast was excellent. Pool could be a lot warmer. Multiple people came in to pool area, put feet in the water, tried to get into the water but then left a few minutes after not going in.

Reviewed on Aug. 23, 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 $558 per night from Sep 11 to Sep 12
CA $558
CA $642 total
Sep 11 - Sep 12
includes taxes & fees
9.4/10 Exceptional! (312 reviews)
"The hotel is beautiful and the grounds are wonderful. The staff was top notch. We will definitely stay again."

Reviewed on Aug. 18, 2025

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 CA $98 per night from Sep 25 to Sep 26
CA $98
CA $115 total
Sep 25 - Sep 26
includes taxes & fees
6.8/10 (1,011 reviews)
"Great location, quiet & yet right near Rt 95. Clean, nice room, polite staff!!!"

Reviewed on Aug. 25, 2025

Motel 6 New Haven - Branford, CT
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 $145 per night from Aug 31 to Sep 1
CA $145
CA $167 total
Aug 31 - Sep 1
includes taxes & fees
7.8/10 Good! (1,304 reviews)
"Staff was very friendly and knowledgeable of the area."

Reviewed on Aug. 22, 2025

Best Western Executive Hotel Of New Haven - West Haven
See all 1,910 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
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Madison vacation package cost?
You can pick up a vacation package to this popular destination from CA $858 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.