Deals on vacations and trips to Madison

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Madison flight + hotel vacation packages

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

Casco Bay Inn

2 out of 5
Price was $341, price is now $293 per person
$293
per person
Jan 15 - Jan 18
found 14 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Portland (PWM)
This hotel features free self parking and free WiFi in public areas. Enjoy the free continental breakfast each morning. A terrace is also provided.
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Price was $564, price is now $466 per person
$466
per person
Jan 23 - Jan 25
found 8 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) 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.
Hilton Garden Inn Freeport Downtown

Hilton Garden Inn Freeport Downtown

3 out of 5
Price was $525, price is now $451 per person
$451
per person
Jan 30 - Feb 2
found 1 day ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Portland (PWM)
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the gym and perks like free self parking.
Inn By The Sea

Inn By The Sea

4 out of 5
Price was $602, price is now $526 per person
$526
per person
Jan 23 - Jan 25
found 8 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Portland (PWM)
A full-service spa, a 24-hour gym, and a restaurant are all featured at this smoke-free hotel. Families will appreciate the playground, onsite laundry facilities, and free supervised childcare. Enjoy the outdoor pool and perks like free valet parking.
Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
West End
Price was $595, price is now $521 per person
$521
per person
Jan 23 - Jan 25
found 8 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) 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.

Top Madison hotels deals

Purity Spring Resort

Purity Spring Resort

2 out of 5
1251 Eaton Rd Madison NH
Free Cancellation
Reserve now, pay when you stay
$119 nightly
The price is $129 total per night
$129 total
Dec 17 - Dec 18
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.
Pool
Parking included
North Conway Grand Hotel

North Conway Grand Hotel

4 out of 5
72 Common Court North Conway NH
Free Cancellation
Reserve now, pay when you stay
$119 nightly
The price is $130 total per night
$130 total
Jan 6 - Jan 7, 2026
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.
Pool
Hot Tub
Grand Summit Hotel at Attitash

Grand Summit Hotel at Attitash

3 out of 5
104 Grand Summit Road Bartlett NH
Free Cancellation
Reserve now, pay when you stay
$109 nightly
The price is $118 total per night
$118 total
Dec 17 - Dec 18
Total with taxes and fees
Ski-in/ski-out access and an outdoor pool are featured at this smoke-free hotel. Take advantage of ski passes and ski storage on site. Enjoy a meal from the restaurant and perks like free self parking and free WiFi.
Pool
Parking included
Eastern Inn & Suites

Eastern Inn & Suites

2 out of 5
2955 White Mountain Highway, Route 16 North Conway NH
$146 nightly
The price is $158 total per night
$158 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
This motel features an indoor pool and a 24-hour gym. There's fun for all ages with a playground and an arcade/game room, and families will appreciate the onsite laundry facilities. Guests will appreciate free perks like free self parking and WiFi in public areas.
Pool
Parking included
Green Granite Inn, an Ascend Collection Hotel

Green Granite Inn, an Ascend Collection Hotel

2.5 out of 5
1515 White Mountain Hwy North Conway NH
Free Cancellation
$51 nightly
The price is $55 total per night
$55 total
Jan 14 - Jan 15, 2026
Total with taxes and fees
This hotel features an indoor pool and a gym. There's fun for all ages with a playground and an arcade/game room, and families will appreciate the onsite laundry facilities. Enjoy the seasonal outdoor pool and free perks like continental breakfast and free self parking.
Pool
Breakfast included
Residence Inn by Marriott, North Conway

Residence Inn by Marriott, North Conway

3 out of 5
1801 White Mountain Highway North Conway NH
Free Cancellation
Reserve now, pay when you stay
$127 nightly
The price is $137 total per night
$137 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the hot tub and free perks like buffet breakfast and free self parking.
Pool
Hot Tub
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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 $293. 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.

Photos of local treasures

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