Caiolo Vacations from $1,054

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Your Caiolo Vacation

Book a Caiolo vacation package and prepare to experience the highlights of this city. Consider staying in the neighborhood of San Simone, which is good for families, hiking and walking. If your trip to Caiolo includes a little sightseeing, check out renowned attractions like Grumello Castle, Masegra Castle Museum and Valtellinese Museum of History and Art. No matter your travel plans or budget, organizing a tailored Caiolo vacation is a breeze with Expedia.

The Latest Caiolo vacation packages

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

Hotel Oleggio Malpensa

3 out of 5
Price was $2,096, price is now $1,054 per person
$1,054
per person
Aug 24 - Aug 28
found 1 day ago
Roundtrip non-stop flight included
Miami (MIA) to Milan (MXP)
8.8/10 Excellent! (548 reviews)
Communication was impressive! We were checking in late and they sent a very specific email stating how that should be done. The room was spacious and clean. The breakfast in the morning was extensive and delicious. The staff all were very nice, helpful and professional!

Reviewed on Jun 14, 2026

Hotel Ristorante Vecchia Riva

Hotel Ristorante Vecchia Riva

3 out of 5
Price was $2,267, price is now $1,169 per person
$1,169
per person
Aug 24 - Aug 28
found 3 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Milan (MXP)
9.2/10 Wonderful! (98 reviews)
The hotel is by Lake Varese which is a bonus. Parking is big enough. Staff was really helpful and friendly.

Reviewed on Mar 27, 2026

Crowne Plaza Milan - Malpensa Airport by IHG

Crowne Plaza Milan - Malpensa Airport by IHG

4 out of 5
Case Nuove
Price was $2,143, price is now $1,111 per person
$1,111
per person
Aug 24 - Aug 28
found 1 day ago
Roundtrip non-stop flight included
Miami (MIA) to Milan (MXP)
8.4/10 Very Good! (1,000 reviews)
The property close to the airport was a great advantage.The following day a shuttle provided by the hotel picked us up and took us to the airport. Excellent service overall.

Reviewed on Jun 13, 2026

Motel Hotel Piranha

Motel Hotel Piranha

4 out of 5
Price was $2,189, price is now $1,141 per person
$1,141
per person
Aug 24 - Aug 28
found 3 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Milan (MXP)
8.8/10 Excellent! (84 reviews)
I should have guessed by the fact you can reserve a room by the hour, what kind of hotel this was. The walls were paper thin so that you could hear the piped music in the hall all night long, as if there was a party somewhere, and people constantly clattering around. The bed was big but the pillow rock hard and the mirror on the ceiling very interesting!

Reviewed on Oct 18, 2025

Hotel dei Tigli

Hotel dei Tigli

3 out of 5
Price was $2,196, price is now $1,151 per person
$1,151
per person
Aug 24 - Aug 28
found 1 day ago
Roundtrip non-stop flight included
Miami (MIA) to Milan (MXP)
8.8/10 Excellent! (17 reviews)
Great location in Angera for this 3 star hotel. Staff were extremely friendly, helpful and welcoming and it felt like a family-run establishment. It was a little rough around the edges in places (e.g. minibar fridges could do with a good clean), but overall a very pleasant stay and would recommend this hotel to anyone staying in Angera!

Reviewed on Sep 16, 2019

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Caiolo Hotel Deals

Agriturismo B&B Caffè e Vino

Agriturismo B&B Caffè e Vino

Via Roi 102 Caiolo SO
Fully refundableReserve now, pay when you stay
$130 nightly
The price is $144 total per night from Jun 23 to Jun 24
$144 total
Jun 23 - Jun 24
Total with taxes and fees
9.6/10 Exceptional! (9 reviews)
"Amazing place, very quite and peaceful. Close to lots of restaurants and not too far from some good Ski resorts.Great hosts and very clean and well maintained rooms."

Reviewed on Feb 2, 2026

Agriturismo B&B Caffè e Vino
Agriturismo Ribuntà

Agriturismo Ribuntà

Frazione San Bernardo 52, 23010 Caiolo, Italy Caiolo SO
$98 nightly
The price is $108 total per night from Jul 23 to Jul 24
$108 total
Jul 23 - Jul 24
Total with taxes and fees
Agriturismo Ribuntà
Bernina Suites - 150 metres to Bernina Express

Bernina Suites - 150 metres to Bernina Express

Via Cabasso 11 Tirano SO
$109 nightly
The price is $125 total per night from Jun 23 to Jun 24
$125 total
Jun 23 - Jun 24
Total with taxes and fees
9.6/10 Exceptional! (252 reviews)
"Central location five minutes away from the train station. Clean, equipped with a kitchen, good size unit. Helpful staff."

Reviewed on Jun 17, 2026

Bernina Suites - 150 metres to Bernina Express
See all 848 properties in Caiolo
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 Caiolo Vacation Packages

Caiolo Essential Information

Language
Italian
Currency
Euros
Local Welcome
Ciao
Local Goodbye
Ciao
Population
850
Top Sights
Valmalenco – Alpe Palù Ski Area, Masegra Castle Museum and Grumello Castle

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Frequently asked questions

How much does a Caiolo vacation package cost?
You can snap up a vacation package to this destination from $1,054 on Expedia. But how much your vacation to Caiolo costs will depend on factors like the season, hotel choice and length of stay.
What are the cheapest months to go to Caiolo?
January, April and December are the best times to look for cheap Caiolo vacation packages. Opting to travel in quieter periods means you can typically find lower prices on flights and accommodations.
How many days is enough for Caiolo?
The ideal duration for your Caiolo vacation depends on what you'd like to do and see. Generally, a handful of days to a week will give you enough time to visit all the top sights and discover some hidden gems along the way.
How to find the best Caiolo package deals?
Start your search for a Caiolo package deal by entering your destination and travel dates under our "Packages" tab. Then apply a few filters, like "Popular locations" and "Property type," to fine-tune the results to your exact style. You can also sort by "Package discount" and discover offers that come with big savings. If you don't find the perfect Caiolo package deal right away, just switch up your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Caiolo getaway off to a flying start.
Is it cheaper to book a Caiolo vacation as a package?
You can enjoy significant savings on your Caiolo escape by booking a personalized vacation package. Check the "Package" heading, then enter your destination and travel dates to view some great airfares and hotel prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Caiolo?
If you're planning an impromptu Caiolo trip, check out our last-minute deals that can be booked up to a week before you take off. Don't want to leave things to the last minute? You can land sensational deals on your flights and hotels by booking well in advance.
Does Expedia offer Book Now, Pay Later Caiolo vacation packages?
Secure your dream getaway to Caiolo with help from Expedia's Book Now, Pay Later vacations. There's no need to save like crazy or wait until payday — we've partnered with online lender Affirm to give you more flexibility and choice. Our vacation packages with payment plans allow you to spread the cost over 3, 6 or 12 months. With no hidden or late payment fees, it's a breeze to stick to your budget and snap up bargains while they last.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.