Deals on vacations and trips to Madison

Save when you book Madison package deals

Choose two or more items and save on your trip:

Madison flight + hotel vacation packages

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

Portland Harbor Hotel

4 out of 5
Downtown Portland
Price was $1,241, price is now $886 per person
$886
per person
May 17 - May 22
found 1 day 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 McKernan Inn

The McKernan Inn

3 out of 5
Price was $1,339, price is now $981 per person
$981
per person
May 22 - May 27
found 3 hours ago
Roundtrip non-stop flight included
Milwaukee (MKE) to Portland (PWM)
This inn features free WiFi in public areas, concierge services, and free self parking. Enjoy the free continental breakfast each morning. A garden, a picnic area, and luggage storage are also on offer.
The Docent's Collection at 121 Middle Street

The Docent's Collection at 121 Middle Street

3.5 out of 5
Downtown Portland
Price was $1,227, price is now $908 per person
$908
per person
May 17 - May 22
found 1 day 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.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
West End
Price was $1,551, price is now $1,195 per person
$1,195
per person
May 17 - May 22
found 1 day 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

Portland Regency Hotel & Spa

3.5 out of 5
Downtown Portland
Price was $1,136, price is now $891 per person
$891
per person
May 17 - May 22
found 1 day 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

Purity Spring Resort

2 out of 5
1251 Eaton Rd Madison NH
Free Cancellation
Reserve now, pay when you stay
$115 nightly
The price is $125 total per night
$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.
Pool
Parking included
North Conway Grand Hotel

North Conway Grand Hotel

4 out of 5
72 Common Court North Conway NH
$132 nightly
The price is $144 total per night
$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.
Pool
Hot Tub
Hampton Inn & Suites North Conway

Hampton Inn & Suites North Conway

2.5 out of 5
1788 White Mountain Hwy North Conway NH
Free Cancellation
Reserve now, pay when you stay
$89 nightly
The price is $97 total per night
$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.
Pool
Hot Tub
Cambria Hotel North Conway

Cambria Hotel North Conway

3 out of 5
1858 White Mountain Highway North Conway NH
Free Cancellation
$101 nightly
The price is $110 total per night
$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.
Pool
Pet friendly
North Conway Mountain Inn

North Conway Mountain Inn

2.5 out of 5
2114 White Mountain Highway North Conway NH
$89 nightly
The price is $97 total per night
$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.
Parking included
Free WiFi
Comfort Inn & Suites North Conway

Comfort Inn & Suites North Conway

3 out of 5
2001 White Mountain Hwy North Conway NH
Free Cancellation
Reserve now, pay when you stay
$105 nightly
The price is $114 total per night
$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.
Pool
Breakfast included
Don't see what you're looking for?
See all available properties in Madison
View all properties
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 $886. 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

Browse Madison vacation photos for more inspiration

Aerial view of a sunset on a New Hampshire lake in the White Mountains -Madison, NH
Woman trail running in mountains with foliage in autumn
Sunset above Silver Lake,New Hampshire