Madison Vacation Packages 2026 from $785

Madison flight + hotel vacation packages

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

The Westin Portland Harborview

Downtown Portland

$785

per person

May 17 - May 22

found 20 hours ago

Roundtrip non-stop flight included

Milwaukee (MKE) to Portland (PWM)

A full-service spa, a 24-hour gym, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. There's a bar/lounge on site, and laundry facilities and concierge services are also provided.

Portland Harbor Hotel

Downtown Portland

$886

per person

May 17 - May 22

found 20 hours ago

Roundtrip non-stop flight included

Milwaukee (MKE) to Portland (PWM)

This hotel features 3 coffee shops/cafes and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. You'll find a restaurant and a bar/lounge onsite for dining and drinks, along with a 24-hour front desk.

The Docent's Collection at 121 Middle Street

Downtown Portland

$908

per person

May 17 - May 22

found 20 hours ago

Roundtrip non-stop flight included

Milwaukee (MKE) to Portland (PWM)

This hotel features free WiFi in public areas, a virtual front desk, and self parking. Express check-out is provided and the front desk is staffed around-the-clock.

Blind Tiger Portland - Danforth Street.

West End

$1,195

per person

May 17 - May 22

found 20 hours ago

Roundtrip non-stop flight included

Milwaukee (MKE) to Portland (PWM)

This bed & breakfast doesn't skimp on freebies - guests receive free breakfast and free WiFi. Luggage storage and concierge services are also provided.

Portland Regency Hotel & Spa

Downtown Portland

$891

per person

May 17 - May 22

found 20 hours ago

Roundtrip non-stop flight included

Milwaukee (MKE) to Portland (PWM)

A full-service spa, a hot tub, and a restaurant are all featured at this smoke-free hotel. Unwind with a drink at one of the 2 bars/lounges and enjoy freebies like WiFi in public areas and a roundtrip airport shuttle. There's a gym on site, and laundry facilities and concierge services are also offered.

Top Madison hotels deals

Purity Spring Resort

1251 Eaton Rd Madison NH

Free Cancellation

Reserve now, pay when you stay

$115 nightly

$125 total

Mar 23 - Mar 24

Total with taxes and fees

Ski-in/ski-out access and an indoor pool are featured at this hotel. Enjoy the gym and perks like free self parking and free WiFi. A restaurant, a picnic area, and barbecue grills are also provided.

North Conway Grand Hotel

72 Common Court North Conway NH

$132 nightly

$144 total

Mar 23 - Mar 24

Total with taxes and fees

This hotel features an outdoor pool and an indoor pool. Bring the family and enjoy the children's pool, playground, and arcade/game room. Enjoy the gym and perks like free self parking and free WiFi.

Hampton Inn & Suites North Conway

1788 White Mountain Hwy North Conway NH

Free Cancellation

Reserve now, pay when you stay

$89 nightly

$97 total

Mar 29 - Mar 30

Total with taxes and fees

A water park and an indoor pool are featured at this hotel. There's fun for all ages with a children's pool and a waterslide, and families will appreciate the onsite laundry facilities. Enjoy the gym and free perks like buffet breakfast and free self parking.

North Conway Mountain Inn

2114 White Mountain Highway North Conway NH

$89 nightly

$97 total

Mar 27 - Mar 28

Total with taxes and fees

Free WiFi in public areas is available at this motel. Take advantage of the free self parking.

Cambria Hotel North Conway

1858 White Mountain Highway North Conway NH

Free Cancellation

$101 nightly

$110 total

Apr 6 - Apr 7

Total with taxes and fees

This hotel features a restaurant, an indoor pool, and a bar/lounge. Business travelers can take advantage of the free WiFi in public areas. Enjoy the 24-hour gym and perks like free self parking.

Comfort Inn & Suites North Conway

2001 White Mountain Hwy North Conway NH

Free Cancellation

Reserve now, pay when you stay

$105 nightly

$114 total

Mar 23 - Mar 24

Total with taxes and fees

This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.

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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.

Frequently asked questions

How much are vacation packages to Madison?

Enjoy a memorable travel experience in Madison with a vacation package starting from just $785. Reserving your flights and hotels through Travelocity is a breeze. On top of that, our packages will leave you with more money in your pocket for fun.

How long should my Madison vacation be?

Many people choose to spend roughly 3 nights in Madison, but it's ultimately up to you. If you're eager to venture out and explore all the amazing things this location has to offer, why not hang around for a couple of extra nights?

Where can I get the best vacation package deals for Madison?

With around 400 airlines and 1,000,000 hotels around the world, it's hard to beat Travelocity. Look through our comprehensive range and create your dream Madison vacation package. Doesn't it feel amazing when planning a trip is that easy?

Why should I book my Madison vacation package with Travelocity?

Whether you're planning an epic vacation or a last-minute weekend escape, we have lots of exciting destinations to choose from at a great price. What's more, we provide customer support 24/7, high-quality service and a Price Match Guarantee. Save yourself the effort and time and reserve your dream vacation now.

Can I save money on my Madison car rental if I combine it with my hotel or flight?

Absolutely — combine your flight, hotel and car into a Madison vacation package and you can save a ton. With so much to discover in the Madison area, that rental vehicle will make exploring easy. Once you're in the driver's seat, crank up the tunes and make tracks to Fenway Park, a must-see sight around 110 mi from Madison.

Which airport is best for Madison?

Portland Intl. Jetport Airport (PWM), 45 mi east of the city center, is where many visitors begin their Madison adventures. But Lebanon Municipal Airport (LEB) (60 mi away from central Madison) could be a handier option for you.

What is there to do in Madison?

Don't miss the excellent photo opportunities at King Pine Ski Area, one of the most renowned attractions in Madison. There's so much more to discover around this exciting city, so give yourself enough time to visit some lesser-known sights.

Where should I stay when visiting Madison?

Many travelers opt to hit the hay at the Cozy dog-friendly home . It's sure to be a good base for your Madison getaway.