Caiolo Vacations from $1,152

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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 Kronhof

Hotel Kronhof

3.5 out of 5
Price was $2,193, price is now $1,152 per person
$1,152
per person
Feb 23 - Feb 27
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Milan (MXP)
9.6/10 Exceptional! (28 reviews)
Great food, good view, great friendly staff

Reviewed on Jun 30, 2024

Lo Scoiattolo Hotel

Lo Scoiattolo Hotel

4 out of 5
Price was $1,835, price is now $1,328 per person
$1,328
per person
Mar 14 - Mar 21
found 5 hours ago
Roundtrip non-stop flight included
New York (NYC) to Milan (MIL)
9.4/10 Exceptional! (97 reviews)
Abbiamo soggiornato in questo albergo di montagna per 10 giorni e possiamo dire con tutto il cuore che è stata un’esperienza meravigliosa. La struttura è bella, immersa nella natura e curata con amore, ma il vero valore aggiunto sono le persone. Grazie Vali&Kasia Laura, la proprietaria, è stata impeccabile: gentile, attenta e sempre presente con il sorriso. Ma una menzione davvero speciale va a Bogdan, Daniel e Christos: tre persone straordinarie che ci hanno fatto sentire accolti, coccolati e parte di una grande famiglia. Bogdan, con la sua energia e disponibilità, Daniel, con la sua gentilezza e premura, e Christos, con il suo spirito positivo e autentico... ognuno di loro ci ha lasciato qualcosa nel cuore. Grazie a loro, questa vacanza è stata molto più bella di qualsiasi altra vissuta in passato. Se cercate un luogo dove sentirvi davvero bene, questo è il posto giusto.

Reviewed on Apr 6, 2025

Relais & Spa Castello di Casiglio

Relais & Spa Castello di Casiglio

4 out of 5
Price was $1,570, price is now $1,186 per person
$1,186
per person
Mar 9 - Mar 14
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Milan (MXP)
8.4/10 Very Good! (392 reviews)
They had to many guests to have dinner in the restaurant on sight. We were driven to a pizzaria nearby :-(

Reviewed on Sep 27, 2025

Sporthotel Zoll

Sporthotel Zoll

4 out of 5
Price was $2,296, price is now $1,219 per person
$1,219
per person
Feb 23 - Feb 27
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Milan (MXP)
9/10 Wonderful! (93 reviews)
One of the best places I have stayed for attention to details and quality!

Reviewed on Apr 8, 2025

Casa Baglioni Milan - The Leading Hotels of the World

Casa Baglioni Milan - The Leading Hotels of the World

5 out of 5
Milan Centre
Save 100% on your flight
Price was $7,478, price is now $4,466 per person
$4,466
per person
Mar 15 - Mar 21
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Milan (LIN)
9.8/10 Exceptional! (91 reviews)
Very clean and discreetly attentive staff

Reviewed on Dec 27, 2025

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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
$155 nightly
The price is $170 total per night from Jan 6 to Jan 7
$170 total
Jan 6 - Jan 7
Total with taxes and fees
10/10 Exceptional! (5 reviews)
Adorável hospedagem
Adorável local

Reviewed on Feb 28, 2025

Agriturismo B&B Caffè e Vino
Bernina Suites -2min walk to Bernina Exp

Bernina Suites -2min walk to Bernina Exp

Via Cabasso 11 Tirano SO
$112 nightly
The price is $128 total per night from Jan 11 to Jan 12
$128 total
Jan 11 - Jan 12
Total with taxes and fees
9.4/10 Exceptional! (132 reviews)
Great location, close to train, easy check-in, big clean appartment, well equipped.

Reviewed on Dec 20, 2025

Bernina Suites -2min walk to Bernina Exp
Hotel Stelvio Tirano

Hotel Stelvio Tirano

Via Lungo Adda IV Novembre Tirano SO
Fully refundableReserve now, pay when you stay
$140 nightly
The price is $161 total per night from Jan 13 to Jan 14
$161 total
Jan 13 - Jan 14
Total with taxes and fees
9.6/10 Exceptional! (39 reviews)
Hotel was immaculate, room was small but cute, breakfast was delicious, convenient location to train, and the young lady at the front desk was a gem.

Reviewed on Dec 18, 2025

Hotel Stelvio Tirano
See all 716 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 $1,152 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.