Chianti Region Mountain Vacations 2026/2027

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4 Night Mountain vacations in Chianti Region

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

Villa Castiglione

$886

per person

Dec 6 - Dec 10

found 1 day ago

Roundtrip non-stop flight included

New York (NYC) to Florence (FLR)

8.6/10 Excellent! (276 reviews)

Absolutely wonderful stay, newly refurbished pool, gorgeous airy room, staff were incredibly helpful and informative, great food- but the location!!! Wow wow wow!!! Fantastic value for money and feels like you’re in the heart of tuscany but in easy reach of Florence with a car.

Reviewed on Jul 15, 2026

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How to plan for a mountain vacation in Chianti Region?

The first step to planning your mountain vacation to Chianti Region is to decide what dates you want to go. In the winter months, fresh snowfall means you could hit the slopes at ski resorts near Chianti Region, while summer invites you to enjoy scenic hikes. It's a good idea to choose the type of accommodation you'd prefer, too. On Expedia, you'll encounter a vast array of options in Chianti Region, from famous chain hotels to charming cabins. The vacation planning page has more tips for organizing your Chianti Region mountain vacation.

What amenities should I look for when booking a mountain resort in Chianti Region?

When booking accommodation for your mountain vacation to Chianti Region, check to see if where you're staying has heating. Chianti Region's mountain air means it can feel fresh at night. If you're craving a special stay, look to see if the hotel offers mountain view rooms, or has a pool or hot tub to unwind in the evenings. Expedia's handy search filters include all these amenities and more, making it a breeze to book the right place to stay on your Chianti Region vacation package.

Why should I choose a package for my mountain vacation in Chianti Region?

Choosing a package for your Chianti Region vacation often works out cheaper thanks to the savings you get for bundling up your flights and hotel. You'll typically find it costs more when booking these separately. On Expedia, the green label even shows you how much you're saving. Packages also tend to be more flexible, meaning it's more likely you can cancel for free in case your 2026 plans change. You can usually secure your package by paying a small upfront deposit, whereas booking flights separately requires full payment.

What does a Chianti Region package typically include?

Return flight tickets, your accommodation, and applicable taxes are typically included when you book a mountain vacation package to Chianti Region from $886. Hotels may include breakfast and Wi-Fi, while the airfare may include checked luggage. Certain resorts may even include ski passes. As each Chianti Region vacation package is different, be sure to double-check what's included before you confirm. If you want a hassle-free trip, consider booking Chianti Region all-inclusive vacation packages as these include all meals.

How can I book my Chianti Region on Expedia?

Comparing some of the best deals using the search wizard is one of the first steps to booking your Chianti Region mountain vacation on Expedia. Take advantage of the search filters to narrow down hundreds of options at the click of a button. If you've got a strict budget, use the maximum price filter to set your limit. When you've pinned down your Chianti Region package vacation, book it in just a few clicks. You'll also have the option to spread the cost with Expedia's payment plans.

Why book your Chianti Region mountain vacation with Expedia?

With meaty exclusive deals you won't find anywhere else, you'll keep more cash in your pocket when booking your Chianti Region vacation package on Expedia. No matter your preferences or tastes, you'll find the right place to stay thanks to the wide selection of accommodation. There are even last-minute deals, too. And if that's not enough, join One Key for free. Expedia's reward program lets you earn points on eligible trips and also gives you access to juicy member-only discounts.

Can I cancel my mountain vacation package booking?

Yes, as most of Expedia's mountain vacation packages to Chianti Region are flexible, you can often cancel for free. Doing so is easy, too—log in to the “Trips” section and follow the steps. Don't forget to double-check the cancellation policy before booking, as not all Chianti Region vacation packages are flexible. The good news is Expedia will display this to you before payment. Take advantage of the free cancellation search filter so you'll be able to narrow down your search to view only flexible Chianti Region vacation packages.

What types of mountain accommodations are available in Chianti Region?

5-star hotels, cozy mountain lodges, and quaint bed and breakfasts are some of the most popular types of mountain accommodations for your vacation to Chianti Region. Don't forget to use the filters to home in the amenities you'd like to have, too. Maybe it's a spacious suite with a mountain view or a traditional lobby with a fireplace—you'll find it all with Expedia's easy-to-use search wizard and wide choice of accommodation.

Top Mountain Chianti Region Hotels

Castello di Selvole-Adults Only

Localita Selvole, Vagliagli Radda in Chianti SI

50 min drive from Tenuta Torciano Winery

Stay at this farm stay in Radda in Chianti. Enjoy free parking, an attached winery, and a rooftop terrace. Popular attractions Castello di Albola and Badia a ...

8.4/10 Very Good! (18 reviews)

a lovely warm place to stay

"a wonderful agriturismo with welcoming and warm staff. we felt comfortable from the moment we 1st got there and we didn't want to leave."

Reviewed on Dec 30, 2012

Chiusarella Arceno Rentals Club Chianti Villa exclusive Pool Concierge freeWiFi

CASTELNUOVO BERARDENGA Tuscany

1 hour drive from Tenuta Torciano Winery

Book a stay at this family-friendly villa in Castelnuovo Berardenga. Enjoy free WiFi, private pools, and a fitness center. Popular attractions San Felice Winery ...

10/10 Exceptional! (35 reviews)

"Such a beautiful home in a perfect setting, we immediately felt at home. The daily cleaning service was wonderful and friendly. We loved arriving to a fully stocked kitchen, with enough to make a great meal and several snacks throughout our time. I would highly recommend this home!"

Reviewed on Jul 8, 2026

Casa l'Oca, spacious and bright in the heart of Tuscany at the gateway to Chianti.

Ponte Agli Stolli Tuscany

53 min drive from Tenuta Torciano Winery

Stay at this vacation home in Figline e Incisa Valdarno. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Querciabella and Savignola Winery ...

9.2/10 Wonderful! (17 reviews)

"We enjoyed our spot which was relatively close to Florence and equally close to the region we wanted to explore. We had plenty of room for four adults to spread out, found all the things we needed and found Valentina to be extremely helpful!"

Reviewed on Sep 2, 2026

See all 4,909 properties in Chianti Region

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.