Monticello Holidays
- Plan, book, travel with confidence
- Better togetherSave up to €900 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top Flight + Hotel Deals in Monticello
Price found within the past 48 hours. Click for updated prices.
Silversmith Hotel Chicago Downtown
Downtown Chicago
€2,143
per person
8 Oct - 13 Oct
found 17 hours ago
Return flight included
Athens (ATH) to Chicago (ORD)
9.2/10 Wonderful! (2,373 reviews)
Hotel could be cleaner. Room was not ready by check in time. Maintenance crew walked into our hotel room while we were there, they didn’t know they had already checked us into the room.
Reviewed on 31 Aug 2026
Top hotels in Monticello
3 Bedroom, 2 Bath House, Large Yard, 4 Miles From New Glarus, 10 Miles To Monroe
Monticello WI
10/10 Exceptional! (165 reviews)
"Check in and check out was an easy process. Instructions from the host were very clear. The big yard and spot on the hill made for a real sense of getting away. The bed was comfortable and the stay was exactly what we needed."
Reviewed on 16 Aug 2026
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 18 Nov 2025
AmericInn by Wyndham Madison West
516 Grand Canyon Dr Madison WI
Fully refundableReserve now, pay when you stay
€71
7 Sept - 8 Sept
includes taxes & fees
9/10 Wonderful! (1,310 reviews)
"Good hotel, clean room, great breakfast, convenient location (14-17min drive to downtown). Thank you!"
Reviewed on 31 Aug 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.
Frequently asked questions
How much does a Monticello holiday package cost?
You can snap up a holiday package to this destination from €1,718 on Expedia. But how much your holiday to Monticello costs will depend on your hotel choice, length of stay and season.
What are the cheapest months to go to Monticello?
To pick up cheap Monticello holiday packages, organise your getaway outside of busy periods like public holidays and major festivals. You'll generally find better availability and lower prices in the off-season or when it's less busy.
How many days is enough for Monticello?
The ideal length of your Monticello holiday depends on what you'd like to see. Usually, a handful of days to a week will give you time to hit all the major attractions and explore 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 travelling on a weekday, when prices are often lower.
Is it cheaper to book a Monticello holiday as a package?
An Expedia holiday 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 holiday 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.
How to plan a trip to Monticello?
- Choose when to travel: Check your calendar and get packing. Your preferred time of year and the activities available will also help you decide when to holiday in Monticello.
- Set a budget: Factor in expenses like transportation, flights and meals when working out how much to set aside for your trip to Monticello. Then, pick a hotel that fits your budget, whether that's a wallet-friendly stay or a more luxurious getaway.
- Decide your trip length: Consider how much time you want to spend exploring Monticello. Plan your itinerary so you can get to all the attractions and experiences you're interested in at a leisurely pace.
- Bundle your bookings: With your travel dates in order, you can combine your hotels, car rental, flights and more into a customised Monticello holiday package.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
