Madison Vacation Packages 2026 from $875

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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.

Landing Furnished Apartment Near Yale University

Downtown New Haven

$875

per person

Dec 29 - Jan 2

found 1 day ago

Roundtrip flight included

Tampa (TPA) to New Haven (HVN)

2/10 (2 reviews)

Check in automated, but the key box was broken and it took me 30 on the phone with IT to get the keys. When I entered the apartment a water leak in the city had destroyed a chunk of the ceiling and there was a mess of drywall and dirty water on the floor. The firm tried to relocate me an hour away before promising to clean up and repair the problem while I was out, but maintenance never arrived. We had to book a hotel nearby. These people are incompetent

Reviewed on Sep 14, 2026

Beechmont - Perfect for Family Retreat!

North End

Save 100% on your flight

$1,041

per person

Nov 13 - Nov 15

found 8 hours ago

Roundtrip flight included

Orlando (MCO) to New Haven (HVN)

No reviews

Hyatus Luxury Residences City Crossing

The Hill

$915

per person

Dec 29 - Jan 2

found 1 day ago

Roundtrip flight included

Tampa (TPA) to New Haven (HVN)

9.4/10 Exceptional! (34 reviews)

The room was spacious and clean. Close to new haven union station, yale university and downtown. We enjoyed the pool, gym and the rooftop. Check in and check out process were very smooth. Sarah was very responsive to our questions. Would def stay here again.

Reviewed on Aug 10, 2026

Landing Apartments New Haven Near Dixwell

Newhallville

$1,036

per person

Dec 29 - Jan 2

found 1 day ago

Roundtrip flight included

Tampa (TPA) 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

Luxury Furnished Apartments by Hyatus Downtown at Yale

The Hill

$1,005

per person

Dec 29 - Jan 2

found 1 day ago

Roundtrip flight included

Tampa (TPA) to New Haven (HVN)

9.6/10 Exceptional! (88 reviews)

Overall, we really enjoyed our stay. The property was just as advertised—spacious, clean, modern, and comfortable, with a nice view of New Haven and a great location convenient to shops and the Yale campus. The apartment was thoughtfully stocked with toiletries, kitchen essentials, linens, and plenty of towels, which was a nice touch. Check-in involved several steps with door codes, garage access, and parking passes, so it took a little more effort than we expected after a long day of travel, but everything worked out fine. The building itself was very quiet, although some road traffic could be heard from the apartment at times. Overall, this was a comfortable, well-equipped, and conveniently located place to stay, and we would happily recommend it to others visiting New Haven.

Reviewed on Oct 6, 2026

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

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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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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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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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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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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East Wharf Beach Park

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

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Madison Hotel Deals

Madison Beach Hotel

94 West Wharf Road Madison CT

$319 nightly

$367 total

Nov 1 - Nov 2

Total with taxes and fees

9.6/10 Exceptional! (392 reviews)

"Great view."

Reviewed on Oct 5, 2026

New Haven Hotel

229 George Street New Haven CT

Fully refundableReserve now, pay when you stay

$120 nightly

$138 total

Oct 27 - Oct 28

Total with taxes and fees

9.2/10 Wonderful! (2,367 reviews)

"Room is average but more spacious than we thought. AC fan is loud. TV remote is sticky, it might not be wiped and cleaned for a while. Location is good but parking is a problem. Public parking lot charges less if you check out early. Reception people are indifferent and reluctant to introduce details ..."

Reviewed on Oct 7, 2026

Motel 6 New Haven - Branford, CT

320 E Main St Branford CT

Fully refundable

$67 nightly

$77 total

Nov 1 - Nov 2

Total with taxes and fees

See all 1,989 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.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	31.3°F (-0.4°C)	Light Rain	Mostly Sunny	Average	Slightly Low
February	32.4°F (0.2°C)	Light Rain	Mostly Sunny	Average	Slightly Low
March	38.5°F (3.6°C)	Light Rain	Mostly Sunny	Average	Average
April	48.2°F (9.0°C)	Light Rain	Mostly Sunny	Average	Average
May	57.9°F (14.4°C)	Light Rain	Mostly Sunny	Average	Average
June	66.4°F (19.1°C)	Light Rain	Mostly Sunny	Moderately High	Slightly High
July	73.8°F (23.2°C)	Light Rain	Mostly Sunny	Moderately High	Slightly High
August	72.7°F (22.6°C)	Light Rain	Mostly Sunny	Moderately High	Slightly High
September	66.2°F (19.0°C)	Light Rain	Mostly Sunny	Average	Average
October	56.5°F (13.6°C)	Light Rain	Mostly Sunny	Moderately Low	Average
November	45.5°F (7.5°C)	Light Rain	Mostly Sunny	Moderately Low	Average
December	37.8°F (3.2°C)	Light Rain	Mostly Sunny	Moderately Low	Slightly 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

What's included in a Madison vacation package?

A Madison vacation package lets you combine round-trip flights, a hotel stay, and a rental car for convenient travel planning. As a beach destination, Madison features many hotels with easy access to the shore, and nearly a third of package hotels feature ocean views. Many properties also provide amenities like free breakfast and airport shuttle service to and from airports such as JFK-John F. Kennedy Intl. (JFK).Exactly what's included will vary by hotel and package, so it's worth reviewing the details before you confirm your booking.

How can I save money on a Madison vacation package?

When you bundle, you can save up to 30%*. To save money on a Madison package, consider traveling during the quieter months or be flexible with your dates to find more options. Bundling your flights and hotel together often unlocks savings compared to booking separately. *Members only. Savings vary.

What's the best vacation package for Madison?

For a romantic or luxury Madison vacation package, consider a stay at the 4-star Madison Beach Hotel. Rated 8.9 out of 10, this property costs around $780 per night and offers a spa, restaurant, and bar/lounge, with travelers often praising the friendly staff and clean rooms. It's located about 3 miles from Hammonasset Beach State Park.If you're seeking a charming couples getaway, The Scranton Seahorse Inn, rated 9.2 out of 10, is a strong choice at around $420 per night. This inn provides free breakfast and is pet-friendly, and travelers frequently highlight the good-sized rooms and overall cleanliness, with breakfast often going the extra mile. It's about 2 miles from Hammonasset Beach State Park.For a best value option, The Homestead, rated 9.6 out of 10, offers packages starting around $400 per night. This hotel includes free breakfast and is pet-friendly, with travelers praising its excellent rooms and great breakfast, contributing to a homey overall feel. It's about 3 miles from Hammonasset Beach State Park.*Package availability and prices may change depending on dates and demand.

Is Madison better suited for a beach vacation or a cultural trip?

Madison is primarily a beach destination, offering a relaxing coastal experience for your Madison vacation. Nearly a third of package hotels feature ocean views, and you can enjoy the expansive shoreline at places like Hammonasset Beach State Park and Hammonasset Beach.While beaches are a major draw, Madison also has cultural elements for a well-rounded Madison vacation package. You can explore historic sites such as the Deacon John Grave House or visit the E.C. Scranton Memorial Library, known for its architecture. Your Madison vacation can easily combine beach relaxation with local historical exploration.

What's included in a Madison beach vacation package?

Madison beach vacation packages typically bundle flights with a hotel stay, offering a convenient way to explore this coastal area. Nearly a third of package hotels here feature ocean views, enhancing the beach experience. For example, the 4-star Madison Beach Hotel, rated 8.9 out of 10, is about 3 miles from Hammonasset Beach State Park and offers amenities like a restaurant, spa, and bar/lounge, with travelers often highlighting its clean rooms and friendly staff. Another excellent option is The Scranton Seahorse Inn, rated 9.2 out of 10, located about 2 miles from Hammonasset Beach State Park, which provides free breakfast and is praised for its good-sized rooms and food. Specific inclusions like meals, drinks, or activities depend on the hotel and the rate you choose for your Madison vacation package.

What are the top things to do in Madison?

For a Madison vacation, you'll find plenty of outdoor activities and scenic beaches to explore:Browse and book things to do in Madison on Expedia to enhance your best vacation packages in Madison.

Do you need to rent a car in Madison, or is public transport enough?

For a Madison vacation package, a rental car offers the most flexibility, especially if you plan to explore beyond your hotel. Madison is well-connected by major roads like Interstate 95 and US Highway 1, though these can experience considerable traffic in more populated areas.While many hotels, such as The Homestead, The Scranton Seahorse Inn, and Madison Beach Hotel, offer airport shuttle services to and from John F. Kennedy Intl. Airport (JFK) (about 75-76 miles away), attractions like Hammonasset Beach State Park (about 2 miles from central Madison) and Gillette Castle State Park (about 17 miles from central Madison) are spread out. A car is highly recommended for a Madison beach vacation package if you wish to visit these sites or other coastal towns at your own pace.

Are Madison vacation package hotels conveniently located?

Madison vacation package hotels are generally conveniently located, with many properties within easy reach of central Madison and its coastal attractions. For instance, The Scranton Seahorse Inn, rated 9.2 out of 10, is about 1 mile from central Madison, and travelers often praise its clean rooms and good-sized accommodations.The Homestead, rated 9.6 out of 10, sits about 2 miles from central Madison, with guests frequently highlighting its convenient location and homey atmosphere. The 4-star Madison Beach Hotel, also about 2 miles from central Madison, is another popular choice, where travelers appreciate the friendly staff and clean rooms. These locations make it easy to access local beaches and town amenities during your stay.

Can I change or cancel my Madison vacation package if my plans change?

Yes, you can cancel your vacation package via your itinerary page on Expedia or by contacting customer service. Remember that some packages are fully refundable, but the details vary based on each unique booking. A fully refundable package may depend on how far out from the travel dates you're canceling and what airline you are traveling with.

Do One Key members get extra savings when booking Madison vacation packages?

Yes, members who join our free One Key™ travel rewards program can instantly unlock additional savings and save 10% or more on over 500,000 stays worldwide with Member Prices and over 1 million car rentals.

Does Expedia offer Book Now, Pay Later Madison vacation packages?

Yes, with Expedia's Book Now, Pay Later option, powered by Affirm, you can spread the cost of your Madison vacation over 3, 6, or 12 months. With no late payment fees or hidden costs, it's easy to secure your ideal vacation package as soon as you spot it.

How do I find last-minute vacation packages to Madison?

To find last-minute vacation packages to Madison, explore the last-minute deals section for the latest package offers, including flights, departing in the coming weeks. Being flexible with your travel dates and hotel preferences can help you secure the best prices.

How does free cancellation work on Madison vacation packages?

Free cancellation on a Madison vacation package depends on the specific hotel and rate combination you book. Many bookings allow free cancellation up to a stated deadline (often a few days before travel) where eligible. Read the cancellation terms carefully when reviewing the package, and visit Expedia help center for further details.

Is it cheaper to book a Madison vacation as a package or separately?

Booking flights and hotels together can unlock lower overall prices. Better still, you can tailor your Madison getaway to match your exact preference. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.

Why should I book my Madison vacation package with Expedia?

Booking your vacation package on Expedia makes it easier to get more out of your trip from the start. With a wide choice of hotels, you can compare prices, reviews and amenities all in one place, then bundle your hotel with flights which could help you save even more. Flexible booking options on selected stays also make it easier to plan with confidence.

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Things to do in Connecticut

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

Madison Vacations from $875

Book a Hotel + Flight or Car together to unlock savings

Room 1

Plan, book, travel with confidence

Better together

Find the right fit

Rest easy

Your Madison Vacation

The Latest Madison vacation packages

Landing Furnished Apartment Near Yale University

Beechmont - Perfect for Family Retreat!

Hyatus Luxury Residences City Crossing

Landing Apartments New Haven Near Dixwell

Luxury Furnished Apartments by Hyatus Downtown at Yale

Stay near popular Madison attractions

Hammonasset Beach State Park

Hammonasset Beach

Madison Green Historic District

Allis-Bushnell House and Museum

Scranton Memorial Library

North Madison Shopping Center

RJ Julia Booksellers

East Wharf Beach Park

Madison Hotel Deals

Madison Beach Hotel

New Haven Hotel

Motel 6 New Haven - Branford, CT

Find the Best Madison Vacation Packages

Things to do in and around Madison

Find the best attractions in and around Madison

Best time to go to Madison

Tips to save on your trip to Madison

Madison Essential Information

More vacations you might like

Frequently asked questions

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