Middleton Vacation Packages 2026 from $457

Middleton flight + hotel vacation packages

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

Sunset Bay Resort & Suites

$457

per person

Sep 17 - Sep 21

found 4 hours ago

Roundtrip flight included

Chicago (CHI) to Madison (MSN)

A private beach and an indoor pool are featured at this smoke-free 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 seasonal outdoor pool and perks like free self parking.

Madison Marriott South

Save 100% on your flight

$909

per person

Oct 8 - Oct 15

found 22 hours ago

Roundtrip flight included

Chicago (CHI) to Madison (MSN)

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 24-hour gym and perks like free self parking.

Fairfield by Marriott Inn & Suites Madison South

Save 100% on your flight

$890

per person

Oct 8 - Oct 15

found 22 hours ago

Roundtrip flight included

Chicago (CHI) to Madison (MSN)

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

Graduate by Hilton Madison

Downtown Madison

Save 100% on your flight

$1,592

per person

Sep 30 - Oct 4

found 1 day ago

Roundtrip flight included

Chicago (CHI) to Madison (MSN)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas and valet parking. There's a rooftop terrace on site, and a 24-hour front desk and a coffee shop are also provided.

Courtyard by Marriott Madison East

$927

per person

Oct 8 - Oct 15

found 23 hours ago

Roundtrip flight included

Chicago (CHI) to Madison (MSN)

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the 24-hour gym and perks like free self parking.

Top Middleton hotels deals

Country Inn & Suites by Radisson, Middleton - Madison West

2212 Deming Way Middleton WI

Free Cancellation

$77 nightly

$87 total

Aug 30 - Aug 31

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 continental breakfast and free self parking.

Pool

Hot Tub

Hilton Garden Inn Madison West/Middleton

1801 Deming Way Middleton WI

Free Cancellation

Reserve now, pay when you stay

$94 nightly

$106 total

Aug 23 - Aug 24

Total with taxes and fees

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas and free internet in public areas. Enjoy the gym and perks like free self parking.

Pool

Pet friendly

Fairfield Inn & Suites by Marriott Madison West/Middleton

8212 Greenway Blvd Middleton WI

Free Cancellation

Reserve now, pay when you stay

$93 nightly

$105 total

Sep 7 - Sep 8

Total with taxes and fees

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

Pool

Breakfast included

Holiday Inn Express & Suites Madison West - Middleton by IHG

8353 MURPHY DRIVE Middleton WI

Free Cancellation

$84 nightly

$95 total

Aug 23 - Aug 24

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, free WiFi in public areas, and free airport shuttle. Guests will appreciate freebies like buffet breakfast and free self parking.

Pool

Breakfast included

Courtyard by Marriott Madison West Middleton

2266 Deming Way Middleton WI

Free Cancellation

Reserve now, pay when you stay

$87 nightly

$99 total

Sep 4 - Sep 5

Total with taxes and fees

This hotel features a restaurant, an indoor pool, and a bar/lounge. Bring the family and enjoy the children's pool, waterslide, and kid-friendly dining. Enjoy the gym and perks like free self parking and free WiFi.

Pool

Hot Tub

TownePlace Suites by Marriott Madison West/Middleton

3055 DEMING WAY Middleton WI

$109 nightly

$124 total

Aug 23 - Aug 24

Total with taxes and fees

An indoor pool, free self parking, and barbecue grills are featured at this hotel. Guests will appreciate free perks like continental breakfast and WiFi in public areas. There's a garden and multilingual staff can provide around-the-clock assistance.

Pool

Breakfast included

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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.

Stay near popular Middleton attractions

Capital Brewery

8.6/10 (30 reviews)

Enjoy a trip to Capital Brewery and popular activities like biking in Middleton. Amble around the area's lakeside or attend a sporting event.

See properties

Frequently asked questions

How much are vacation packages to Middleton?

Travelocity has great package deals to Middleton, including hotels and flights, starting at just $457. With the money you save, you could book some popular tours or maybe tack on some extra days to your adventure.

How long should my Middleton vacation be?

Typically, 3 nights is what many tourists book for their Middleton trip. That's a good base to start from, but there's plenty more to explore if you give yourself a little more time.

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

Landing a great package deal to Middleton is a breeze with Travelocity. With as many as 400 partner airlines and 1,000,000 properties all over the globe, you're flush with choice when it comes to your hotels and flights.

Why should I book my Middleton vacation package with Travelocity?

Whether you're searching for the ultimate unplugged escape or you crave the fun and excitement of the big city, booking everything with Travelocity saves you time, money and hassle. No need to sift through hundreds of websites for the best deal — our Price Match Guarantee ensures you'll always get the lowest price, and our team of customer service experts are available 24/7 should you need them.

Can I save on my Middleton car rental if I bundle it with my hotel or flight?

You certainly can — bundle your car, flight and hotel into a Middleton vacation package and you'll save plenty. With so many things to do in the Middleton area, that rental vehicle will make exploring a breeze. Once you've settled into the driver's seat, put the stereo on and make tracks to Wrigley Field, a well-known attraction about 120 mi from Middleton.

Which airport is best for Middleton?

Dane County Regional Airport (MSN) is the arrival point for those flying to Middleton. Once you touch down, you'll be 8 mi east of the center of town.

What is there to do in Middleton?

You'll sense a certain kind of magic as you roam the streets of Middleton. National Mustard Museum and Pleasant View Golf Course are just a couple of famous attractions that make this city such a sought-after destination, so put them on your to-do list.

Where should I stay when visiting Middleton?

The Country Inn & Suites by Radisson, Madison West, WI is popular with many travelers. Book soon before it's too late.