Madison Vacation Packages
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- Plan, book, travel with confidence
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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.
Landing Apartments New Haven Near Dixwell
Newhallville
CA $1,489
per person
Sep 17 - Sep 20
found 11 hours ago
Roundtrip flight included
Vancouver (YVR) to New Haven (HVN)
2/10 (1 review)
The parking situation is very unclear. There is a small sign far from the lot that warns of towing but nothing in the area where you park. No significant warnings in communications with host.
Reviewed on May 25, 2026
Hyatus Luxury Residences City Crossing
The Hill
CA $1,186
per person
Oct 16 - Oct 18
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New Haven (HVN)
9.4/10 Exceptional! (33 reviews)
Everything about the property & staff was AMAZING! Zero complaints, would 100% stay there again if in the area. Thank you!
Reviewed on Jul 24, 2026
New Haven Hotel
Downtown New Haven
CA $1,162
per person
Sep 17 - Sep 20
found 11 hours ago
Roundtrip flight included
Vancouver (YVR) to New Haven (HVN)
9.2/10 Wonderful! (2,266 reviews)
The front desk staff was consistently friendly and helpful. The parking situation was ideal. It was all good!
Reviewed on Aug 8, 2026
Ready to book your vacation to Madison?
Madison Hotel Deals
Madison Beach Hotel
94 West Wharf Road Madison CT
CA $669
CA $769 total
Sep 2 - Sep 3
includes taxes & fees
Motel 6 New Haven - Branford, CT
320 E Main St Branford CT
Fully refundable
CA $88
CA $103 total
Sep 3 - Sep 4
includes taxes & fees
Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd Old Saybrook CT
Fully refundable
CA $137
CA $157 total
Aug 10 - Aug 11
includes taxes & fees
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
Photo by Shannon Willitts
Hammonasset Beach State Park
8.8/10 (137 reviews)
You can take time to visit Hammonasset Beach State Park during your travels to Madison. While you're in the area, stroll along the beautiful beaches.
Hammonasset Beach
9.4/10 (14 reviews)
Why not spend a lazy afternoon at Hammonasset Beach during your trip to Madison? While you're in the area, stroll along the beaches.
North Madison Shopping Center
8.8/10 (10 reviews)
You can search for that perfect souvenir at North Madison Shopping Center during your trip to Madison. While you're in the area, wander around the natural setting.
beach near Madison Center
Why not spend a lazy afternoon at beach near Madison Center during your trip to Madison?
Meigs Point Nature Center
9.0/10 (4 reviews)
Enjoy the collegiate vibe at Meigs Point Nature Center during your stay in Madison. While you're in the area, stroll along the beautiful beaches.
Deacon John Grave House
8.0/10 (2 reviews)
You can spend time studying the exhibits at Deacon John Grave House in Madison. While you're in the area, stroll along the beautiful beaches.
East Wharf Beach Park
Why not spend a lazy afternoon at East Wharf Beach Park during your trip to Madison?
Scranton Memorial Library
8.0/10 (3 reviews)
After visiting Scranton Memorial Library, make a plan to see the other sights and activities in Madison. While you're in the area, stroll along the beautiful beaches.
Frequently asked questions
How much does a Madison vacation package cost?
You can pick up a vacation package to this popular destination from CA $606 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?
- 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.
- 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.
- 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.
- 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.
