Madison Vacations from $302
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The Latest Madison Vacation Packages
- La Quinta Inn & Suites by Wyndham New Haven
Oct 23 - Oct 26La Quinta Inn & Suites by Wyndham New Haven + Flight
Long Wharf3 nights3.0 star property6.0/10 - (1,326 reviews)"We are very satisfied with their service and kindness We highly recommend this hotel"Reviewed July 29, 2026Roundtrip • Cleveland (CLE) - New Haven (HVN)CLE - HVN • Nonstop HVN - CLE • Nonstop$401$302found 18 hours agoper traveler - Landing Apartments New Haven Near Dixwell
Oct 23 - Oct 26Landing Apartments New Haven Near Dixwell + Flight
Newhallville3 nights3.0 star property2.0/10 - (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 May 25, 2026Roundtrip • Cleveland (CLE) - New Haven (HVN)CLE - HVN • Nonstop HVN - CLE • Nonstop - Landing Furnished Apartment Near Yale University
Oct 23 - Oct 26Landing Furnished Apartment Near Yale University + Flight
Downtown New Haven3 nights3.0 star property2.0/10 - (1 review)"Was unable to enter the unit as the key was not available in the Lockbox. Landing (the rental company) was unable to locate the key, which was apparently with the cleaning staff, who were unavailable. We ended up having to rent another property for our visit."Reviewed June 2, 2026Roundtrip • Cleveland (CLE) - New Haven (HVN)CLE - HVN • Nonstop HVN - CLE • Nonstop - Hyatus Luxury Residences City Crossing
Oct 23 - Oct 26Hyatus Luxury Residences City Crossing + Flight
The Hill3 nights4.0 star property9.4/10 - Exceptional (33 reviews)"Everything about the property & staff was AMAZING! Zero complaints, would 100% stay there again if in the area. Thank you!"Reviewed July 24, 2026Roundtrip • Cleveland (CLE) - New Haven (HVN)CLE - HVN • Nonstop HVN - CLE • Nonstop - Graduate by Hilton New Haven
Oct 23 - Oct 26Graduate by Hilton New Haven + Flight
Downtown New Haven3 nights4.0 star property9.2/10 - Wonderful (1,007 reviews)Roundtrip • Cleveland (CLE) - New Haven (HVN)CLE - HVN • Nonstop HVN - CLE • Nonstop
Where to stay in Madison
Madison Center
While visiting Madison Center, you might make a stop by sights like East Wharf Beach Park and Deacon John Grave House.
Discover the most popular places to visit in Madison
Hammonasset Beach State Park
Madison Hotel Deals
Holiday Inn Express Branford-New Haven by IHG
Holiday Inn Express Branford-New Haven by IHG
Baymont by Wyndham Branford/New Haven
Baymont by Wyndham Branford/New HavenFrequently Asked Questions
How much does a Madison vacation package cost?
You can grab a vacation package to this top destination from $302 on Expedia. However, how much your vacation to Madison costs will depend on the season, hotel choice and length of stay.
What are the cheapest months to go to Madison?
November, December and January are great times to search for cheap Madison vacation packages. Traveling in less busy periods means you'll typically find lower prices on flights and hotels.
How many days is enough for Madison?
You can see all the major attractions in Madison in a few days, including the must-see Allis-Bushnell House and Museum. If you're looking for a longer Madison vacation, check out which kind of excursions and activities are available nearby.
Is it worth booking a vacation package to Madison?
Well known for its cafes, dining and a host of other highlights, you can be assured Madison is a good vacation destination. Some of the top attractions to stick on your to-do list? Don't miss Hammonasset Beach State Park and Scranton Memorial Library during your Madison vacation.
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 vacation package as early as possible.
Is it cheaper to book a Madison vacation as a package?
Expedia vacation 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 personalized Madison vacation by choosing your favorite accommodation type, airline and car class.
When to book a vacation 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.
Does Expedia offer Book Now, Pay Later Madison vacation packages?
Your Madison break should be an escape from your busy life, not a source of money worries. So to allow you more flexibility, we've teamed up with online lender Affirm to bring you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and spread the cost over 3, 6 or 12 months. Plus, there aren't any hidden or late payment fees to worry about.
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Things to do in and around Madison
Madison, Connecticut offers a perfect blend of outdoor adventures and scenic beauty, making it an ideal vacation spot. Enjoy walking tours through charming neighborhoods, explore beautiful outdoor gardens, and partake in various free attractions. For those seeking adventure, the recreational area and golf course provide plenty of activities. Don’t miss the chance to catch a lively music concert while soaking in the town's vibrant atmosphere.
Shopping
For shopping in Madison, visit Clinton Crossing Premium Outlets, just 2 miles away, for a variety of brand-name stores. Explore the North Madison Shopping Center for local shops and family-friendly vibes. RJ Julia Booksellers offers a charming selection of books right in town.
Recreation
Experience the charm of the Ivoryton Playhouse, offering captivating performances just 8 miles away. For sports enthusiasts, the Connecticut Sportsplex, located 13 miles from Madison, provides a vibrant athletic atmosphere. Lastly, unwind at East Rock Park, 17 miles away, where you can enjoy nature and relaxation.
Adventure
At Stay and Play LLC, an arcadeAdventureZone 10 miles from Madison, enjoy thrilling games and family-friendly fun. For skiing enthusiasts, Powder Ridge Mountain Park and Resort offers exciting slopes 17 miles away. Don't miss the Lighthouse Point Carousel, a delightful outdoor experience also 17 miles from Madison.
Nightlife
Madison's nightlife offers cozy pubs and vibrant bars. Enjoy craft cocktails at The Wharf and unwind with friends. For live entertainment, check out Madison Beach Hotel for local music, while The Madison Art Cinemas showcases indie films, making for a perfect evening out.
Find the best attractions in and around Madison
Madison, Connecticut, is perfect for outdoor enthusiasts and adventure seekers. Explore stunning state parks, relax on beautiful beaches, and visit historic houses that showcase the area's rich culture. Whether you're looking for scenic views or engaging experiences, Madison offers a variety of attractions that cater to your adventurous spirit.
- Hammonasset Beach State Park: Experience the beauty of Connecticut’s longest beach at Hammonasset Beach State Park, where you can enjoy scenic views, outdoor activities, and adventure. The park offers a perfect setting for swimming, hiking, and picnicking amidst nature’s splendor.
- Essex Steam Train: Just 10 miles from Madison, the Essex Steam Train offers a nostalgic journey through the picturesque Connecticut River Valley. Immerse yourself in the rich culture and history of rail travel while enjoying scenic views aboard a vintage steam locomotive.
- Westbrook Town Beach: Located 6 miles from Madison, Westbrook Town Beach is a serene spot for sunbathing and swimming. With its sandy shores and tranquil atmosphere, it’s the perfect place to relax and soak up the sun.
Best time to go to Madison
The best time to visit Madison can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Madison falls in July, when visitor numbers are moderately high and weather is mostly sunny with light rain. The coolest average temperature in Madison falls in January, visitor numbers are average and weather is mostly sunny with light rain.
Tips to save on your trip to Madison
- Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Madison.
- Consider traveling to Madison during the low season (December to February) for more affordable options.
- Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
- Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.