Monticello Vacations from $397
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Your Monticello Vacation
Amazing adventures await when you book a Monticello vacation package. Whether you're a history buff, foodie or just a traveler who loves discovering new places, there's something for everyone in this vibrant city. New Glarus Brewing Company, Swiss Historical Village and Swissland Miniature Golf are just a few of the many sights worth visiting during your trip to Monticello. Don't delay your visit to this city any longer. The perfect Monticello vacation is a couple of clicks away with Expedia.
The Latest Monticello vacation packages
Price found within the past 48 hours. Click for updated prices.
Chicago Lake Shore Hotel
Kenwood
$397
per person
Nov 26 - Dec 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
7/10 Good! (1,004 reviews)
Great location. Very clean-looks refurbished. The staff is amazing-very helpful & they try to help you have a good experience!
Reviewed on Sep 15, 2026
Monticello Hotel Deals
3 Bedroom, 2 Bath House, Large Yard, 4 Miles From New Glarus, 10 Miles To Monroe
Monticello WI
Jaggi Swiss Gasthaus
Monticello WI
10/10 Exceptional! (44 reviews)
"Host was lovely and very accommodating. Space was very cozy and provided everything I needed. Quick and beautiful drive into New Glarus and surrounding sights. The grounds are perfect and I hope to return in warmer months to enjoy the pool and lush property. Highly recommend!"
Reviewed on Nov 18, 2025
AmericInn by Wyndham Madison West
516 Grand Canyon Dr Madison WI
Fully refundableReserve now, pay when you stay
$70 nightly
$81 total
Sep 21 - Sep 22
Total with taxes and fees
9/10 Wonderful! (1,321 reviews)
"Bed was very comfortable. Breakfast bar had a super selection of various items including fruit."
Reviewed on Sep 17, 2026
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.
Find the Best Monticello Vacation Packages
Monticello Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Dane County Regional Airport (MSN) |
Population | 1,250 |
Top Sights | New Glarus Brewing Company, Minhas Craft Brewery and New Glarus Woods State Park |
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Frequently asked questions
How much does a Monticello vacation package cost?
You can snap up a vacation package to this destination from $397 on Expedia. But how much your vacation to Monticello costs will depend on your hotel choice, length of stay and season.
What are the cheapest months to go to Monticello?
If you're hoping to book a cheap Monticello vacation package, consider visiting in November, December and January. You'll typically find better rates on flights and accommodations during these quieter months — perfect for travelers wishing to save money.
How many days is enough for Monticello?
The ideal length for your Monticello vacation depends on what you'd like to see. Typically, a few days to a week will give you time to hit all the main attractions and discover some hidden treasures along the way.
How to find the best Monticello package deals?
Landing a cheap Monticello package deal is easy with Expedia. Once you've entered your destination and preferred dates under our "Packages" tab, set your budget, apply a couple of filters and browse what's available. You can tweak your search by "Popular locations," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to view the most pocket-friendly Monticello package deals. Want a simple trick to get even more savings? Be flexible with your departure dates and consider traveling on a weekday, when prices are often lower.
Is it cheaper to book a Monticello vacation as a package?
An Expedia vacation package could land you significant savings when compared to booking flights and hotels individually. Better still, you can tailor your Monticello getaway to match your exact style. Choose your preferred flight time, select the hotel type and add a rental car. Explore our bundles to see how much you can save.
When to book a vacation package to Monticello?
Secure incredible bargains by booking your flights early with Expedia. If spontaneity is more your style, take advantage of our last-minute deals for an impromptu Monticello getaway.
Does Expedia offer Book Now, Pay Later Monticello vacation packages?
Your Monticello getaway should be an escape from your daily routine, not a reason for money worries. So to give you more flexibility, we've joined up with online lender Affirm to offer you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and break down the total cost over 3, 6 or 12 months. Plus, there are no hidden or late payment fees to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
