Middleton Vacation Packages 2025/2026 from $461

Middleton flight + hotel vacation packages

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

Bluegreen Odyssey Dells

$461

per person

Oct 3 - Oct 5

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Madison (MSN)

Free water park access and a gym are featured at this smoke-free condo. Families will appreciate the waterslide and onsite laundry facilities. The front desk is staffed around-the-clock and concierge services are on offer.

Bluegreen Christmas Mountain Village, an Ascend Resort

$495

per person

Oct 3 - Oct 5

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Madison (MSN)

A golf course and an indoor pool are featured at this smoke-free resort. Take advantage of ski lessons, ski rentals and ski passes on site, and enjoy downhill skiing. There's fun for all ages with mini golf and a children's pool, and families will appreciate the onsite laundry facilities.

The Madison Concourse Hotel and Governor's Club

Downtown Madison

$928

per person

Oct 24 - Oct 26

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) 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, free WiFi in public areas, and free airport shuttle. There's a gym on site, and a 24-hour front desk and a coffee shop are also provided.

The Wisconsin Hotel & Conference Center

$512

per person

Oct 3 - Oct 5

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Madison (MSN)

This hotel features an indoor pool and a hot tub. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy free perks like free self parking and a casino shuttle.

Christmas Mountain Campground

$469

per person

Oct 3 - Oct 5

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Madison (MSN)

This resort features a golf course, ski-in/ski-out access, and a restaurant. Take advantage of ski lessons, ski rentals and ski storage on site, and enjoy downhill skiing. Bring the family and enjoy the mini golf, waterslide, and playground.

Top Middleton hotels deals

Country Inn & Suites by Radisson, Madison West, WI

2212 Deming Way, Middleton, WI

Free Cancellation

$84 nightly

$96 total

Aug 31 - Sep 1

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

Holiday Inn Express & Suites Madison West - Middleton by IHG

8353 MURPHY DRIVE, Middleton, WI

Free Cancellation

$105 nightly

$119 total

Aug 31 - Sep 1

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

Fairfield Inn & Suites by Marriott Madison West/Middleton

8212 Greenway Blvd, Middleton, WI

Free Cancellation

Reserve now, pay when you stay

$89 nightly

$101 total

Aug 31 - Sep 1

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

Courtyard by Marriott Madison West Middleton

2266 Deming Way, Middleton, WI

Free Cancellation

Reserve now, pay when you stay

$104 nightly

$118 total

Sep 1 - Sep 2

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

Hilton Garden Inn Madison West/Middleton

1801 Deming Way, Middleton, WI

Free Cancellation

Reserve now, pay when you stay

$99 nightly

$113 total

Aug 31 - Sep 1

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

Staybridge Suites Middleton Madison-West by IHG

7790 Elmwood Ave, Middleton, WI

Free Cancellation

$109 nightly

$124 total

Sep 7 - Sep 8

Total with taxes and fees

This hotel features an indoor pool, a 24-hour gym, and a restaurant. 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 on-the-go 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.

Popular places to visit

National Mustard Museum

You can spend an afternoon exploring the galleries in National Mustard Museum in Middleton. Amble around the area's lakeside or attend a sporting event.

Capital Brewery

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

Pleasant View Golf Course

Play a round of golf in Middleton at Pleasant View Golf Course, and enjoy other activities such as biking. Stroll along the lakeside in this family-friendly area, or check out its top-notch restaurants.

Frequently asked questions

How much are vacation packages to Middleton?

Travelocity has great package deals to Middleton, including hotels and flights, starting at just $461. 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.