Madison Vacations from $523

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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.

The Latest Madison vacation packages

Price found within the past 48 hours. Click for updated prices.
New Haven Hotel

New Haven Hotel

Downtown New Haven
Save 100% on your flight
$523
per person
Sep 26 - Sep 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
9.2/10 Wonderful! (2,259 reviews)
We loved the location of the hotel for a visit to Yale. There is a water dispenser near the lobby, complimentary coffee in the morning. The shower was beautiful! The $25 parking fee (with in and out privileges) seemed a bit steep. You could stay in the same parking house for $22+tax if you didn’t need to leave. The hair dryer in the room was not in a good state (smelled burnt straight away) - but I forgot to follow that up. All in all a good place for a stopover in New Haven!

Reviewed on Aug 22, 2026

Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

North End
Save 100% on your flight
$800
per person
Nov 6 - Nov 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
No reviews
Las Flores Villa

Las Flores Villa

Save 100% on your flight
$4,792
per person
Sep 26 - Sep 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
10/10 Exceptional! (1 review)
The Scranton Seahorse Inn

The Scranton Seahorse Inn

Madison Center
Save 100% on your flight
$663
per person
Sep 24 - Sep 28
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to New Haven (HVN)
9/10 Wonderful! (245 reviews)
It sounds like you want this turned into a polished review. Here’s a refined version that keeps the warmth and enthusiasm of what you described: ### An Exceptional Bed & Breakfast Experience I honestly cannot say enough wonderful things about this inn or the innkeeper. From the moment we checked in, everything was absolutely exceptional. Breakfast was truly farm-to-table and felt like such a special experience. We enjoyed a beautiful watermelon, strawberry, and peach salad with fresh herbs, spectacular zucchini muffins, and a delicious quiche. Fresh orange and cranberry juices were served in charming retro carafes, and the coffee was wonderful. There was also an amazing selection of teas. Everything was brought out piping hot and prepared with obvious care. What really made breakfast memorable, though, was the sense of community. Everyone sat together and ate as a group, which captured exactly what a bed and breakfast should be all about. It was warm, welcoming, and genuinely special. The inn itself was immaculate. Our room had absolutely everything we could have needed, including an abundance of helpful information. The bed was incredibly comfortable, the TV was very easy to use, and the closet was huge. Every detail had clearly been thought through. The innkeeper was wonderful—friendly, attentive, knowledgeable, and readily available to answer all of our questions. The level of hospitality truly deserves my highest staff award! We absolutely loved everything about it

Reviewed on Aug 19, 2026

Landing Apartments New Haven Near Dixwell

Landing Apartments New Haven Near Dixwell

Newhallville
Save 100% on your flight
$720
per person
Sep 26 - Sep 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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

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Stay near popular Madison attractions

A rural landscape with a large fallen tree in the foreground, fields, and a forest in the background.
Photo by Shannon Willitts

Hammonasset Beach State Park

8.8/10 (137 reviews)
Connecticut's largest shoreline park features two miles of sandy beach along Long Island Sound. Explore hiking trails or visit the Meigs Point Nature Center for interactive exhibits about local ecosystems.
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A stone pier extending into calm waters at sunset with a person standing at the end.

Hammonasset Beach

9.4/10 (14 reviews)
Connecticut's largest shoreline park offers two miles of sandy beaches along the Long Island Sound. Explore diverse ecosystems on nature trails or visit the Meigs Point Nature Center for wildlife exhibits.
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North Madison Shopping Center

8.8/10 (10 reviews)
This local retail hub offers convenient shopping with a variety of stores and services for everyday needs. Browse through grocery, clothing, and dining options while enjoying the relaxed small-town atmosphere.
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East Wharf Beach Park

Why not spend a lazy afternoon at East Wharf Beach Park during your trip to Madison?
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Scranton Memorial Library

8.0/10 (3 reviews)
The E.C. Scranton Memorial Library has served Madison since 1901 with over 100,000 volumes. Browse their extensive collection or attend one of their frequent author talks and cultural workshops.
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Madison Green Historic District

You can learn about the history of Madison when you stop by Madison Green Historic District.
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Allis-Bushnell House and Museum

8.0/10 (2 reviews)
Step into 1785 at this historic house museum showcasing local artifacts and maritime heritage. Explore period rooms with working looms, spinning wheels, and a charming colonial herb garden.
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RJ Julia Booksellers

9.6/10 (12 reviews)
This beloved independent bookstore hosts over 300 author events annually in its charming two-story space. Browse the thoughtfully curated selection, then relax with your new book at the cozy in-store café.
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Madison Hotel Deals

Madison Beach Hotel

Madison Beach Hotel

94 West Wharf Road Madison CT
$481 nightly
$481 total
Sep 2 - Sep 3
Total with taxes and fees
9.4/10 Exceptional! (383 reviews)
"Everyone was very helpful and accommodating"

Reviewed on Aug 18, 2026

Madison Beach Hotel
Motel 6 New Haven - Branford, CT

Motel 6 New Haven - Branford, CT

320 E Main St Branford CT
Fully refundable
$72 nightly
$83 total
Sep 1 - Sep 2
Total with taxes and fees
7.4/10 Good! (1,012 reviews)
"Room was nice and affordable"

Reviewed on Aug 21, 2026

Motel 6 New Haven - Branford, CT
Sound View Greenport

Sound View Greenport

58775 County Rd 48 Greenport NY
$311 nightly
$355 total
Sep 15 - Sep 16
Total with taxes and fees
8.4/10 Very Good! (695 reviews)
"The views are amazing! The breakfast was a great perk. Short drive to town but you really don't need to leave the grounds with bar/restaurant/beach/pool all there."

Reviewed on Aug 20, 2026

Sound View Greenport
See all 1,999 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.

Find the Best Madison Vacation Packages

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.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

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.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January31.3°F (-0.4°C)Light RainMostly SunnyAverageSlightly Low
February32.4°F (0.2°C)Light RainMostly SunnyAverageSlightly Low
March38.5°F (3.6°C)Light RainMostly SunnyAverageAverage
April48.2°F (9.0°C)Light RainMostly SunnyAverageAverage
May57.9°F (14.4°C)Light RainMostly SunnyAverageAverage
June66.4°F (19.1°C)Light RainMostly SunnyModerately HighSlightly High
July73.8°F (23.2°C)Light RainMostly SunnyModerately HighSlightly High
August72.7°F (22.6°C)Light RainMostly SunnyModerately HighSlightly High
September66.2°F (19.0°C)Light RainMostly SunnyAverageAverage
October56.5°F (13.6°C)Light RainMostly SunnyModerately LowAverage
November45.5°F (7.5°C)Light RainMostly SunnyModerately LowAverage
December37.8°F (3.2°C)Light RainMostly SunnyModerately LowSlightly Low

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.

Madison Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Tweed - New Haven Regional Airport (HVN)
Population
19,100
Max Temp Winter
35ºF
Max Temp Summer
80ºF
Top Sights
Hammonasset Beach State Park, Hammonasset Beach and Stony Creek Museum

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Frequently asked questions

How much does a Madison vacation package cost?
You can grab a vacation package to this top destination from $523 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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.