Castellina in Chianti Vacations from $2,627

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Your Castellina in Chianti Vacation

An easy way to experience this city is with a tailor-made Castellina in Chianti vacation package. Base yourself in the neighborhood of Badia Coltibuono, which is good for families, nature and walking or go someplace else — our package deals are all about you. If sightseeing is on the cards during your trip to Castellina in Chianti, look around well-known attractions like Isole e Olena Winery, Il Molino di Grace Winery and Castello di Radda Winery. Check out Expedia's wide range of travel options and begin planning your ultimate vacation to Castellina in Chianti now.

The Latest Castellina in Chianti vacation packages

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

Villa Le Barone

$2,627
per person
Sep 29 - Oct 2
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Florence (FLR)
9.4/10 Exceptional! (145 reviews)
First let me list the things I loved about the property. The staff is wonderful. They were quick to accommodate requests, were friendly, and kind. The food on the property was delicious. The pool was outstanding, overlooking the Tuscan vineyards. All wonderful. There are drinks and snacks available in various locations on the property, using an honor system to record purchases. There's also a wine dispenser, and the staff provides each guest with a "credit card" for wine purchases. I was disappointed in our apartment. I was unaware that the property was so spread out, with various rooms in different buildings. Our apartment was a distance from the main lodge, and is also more of an air BNB than a hotel. I was expecting hotel service, and that is not what we had. I was expecting our rooms to be cleaned daily, and they weren't cleaned once in our five night stay. We had to go get toilet paper from the main lodge, and ask for towels. Although the rooms in our apartment were spacious, the beds were uncomfortable. The showers in both bathrooms had clogged drains and flooded the floors. The staff did remedy the problem right away. There was no coffee pot available in the apartment-my biggest disappointment. The property as a whole is in a lovely location, and has been family owned for generations. The owner goes out of his way to welcome guests. There are definitely more good things than bad at this property, I'm just not sure I would qualify this as a four star property.

Reviewed on Jun 16, 2026

Gallia Palace Hotel

Gallia Palace Hotel

$2,639
per person
Sep 29 - Oct 2
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Florence (FLR)
9.2/10 Wonderful! (63 reviews)
The hotel staff were super polite and helpful. The food was amazing and the beach was out of this world

Reviewed on Jul 21, 2026

Borgo Scopeto Wine & Country Relais

Borgo Scopeto Wine & Country Relais

$3,028
per person
Sep 29 - Oct 2
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Florence (FLR)
9.4/10 Exceptional! (217 reviews)
We spent a wonderful week at Borgo Scopeto and thoroughly enjoyed every minute. It has everything you'd hope for from a luxury Tuscan retreat: beautiful historic buildings, immaculately kept grounds, and a peaceful atmosphere full of character. The staff were warm, attentive and genuinely welcoming without ever feeling intrusive, and the food was consistently excellent. One of the biggest advantages is its location. Siena is only a short drive away - you can even see the city's campanile while having breakfast - so it was easy to combine days by the pool with exploring one of Tuscany's most beautiful cities (and, inevitably, a bit of shopping to keep our teenage daughter happy). A fantastic place to stay, and one we'd happily recommend.

Reviewed on Aug 5, 2026

Grotta Giusti Thermal Spa Resort Tuscany, Autograph Collection

Grotta Giusti Thermal Spa Resort Tuscany, Autograph Collection

$2,846
per person
Sep 29 - Oct 2
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Florence (FLR)
8.8/10 Excellent! (192 reviews)
Grand Hotel Continental Siena – Starhotels Collezione

Grand Hotel Continental Siena – Starhotels Collezione

Siena City Centre
$3,306
per person
Sep 29 - Oct 2
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Florence (FLR)
9.2/10 Wonderful! (621 reviews)
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Stay near popular Castellina in Chianti attractions

Buondonno Winery

9.6/10 (4 reviews)
You can enjoy a tasting or tour at Buondonno Winery during your travels to Castellina in Chianti. Discover the beautiful countryside and wineries in this relaxing area.
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Archaeological Museum of Chianti

8.0/10 (6 reviews)
You can browse the exhibits at Archaeological Museum of Chianti, a museum with a story of its own, during your trip to Castellina in Chianti. Discover the beautiful countryside in this walkable area, or enjoy its local tours.
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Lilliano Estate Winery

You can enjoy a tasting or tour at Lilliano Estate Winery during your travels to Lilliano.
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Casa Vinicola Luigi Cecchi

9.0/10 (4 reviews)
You can enjoy a tasting or tour at Casa Vinicola Luigi Cecchi during your travels to Castellina in Chianti. Discover the beautiful countryside in this quaint area, or enjoy its local tours.
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Walls of Monteriggioni

9.2/10 (5 reviews)
You can study the exhibits at Walls of Monteriggioni, a museum with a storied past, during your travels to Castellina in Chianti. Discover the beautiful countryside and wineries in this walkable area.
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Castellina Fortress

9.4/10 (3 reviews)
Learn about the local history of Castellina in Chianti when you spend time at Castellina Fortress. Discover the countryside and wineries in this quaint area.
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Mazzei Winery

You can enjoy a tasting or tour at Mazzei Winery during your travels to Fonterutoli. You can enjoy the restaurants while in the area.
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Casina di Cornia Winery

You can enjoy a tasting or tour at Casina di Cornia Winery during your travels to Castellina in Chianti. Discover the countryside and wineries in this relaxing area.
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What to do in Castellina in Chianti

Siena: Cathedral Complex Pass with Audio Guide

Siena: Cathedral Complex Pass with Audio Guide (OPA SI PASS)

$21
per adult
Siena: Cathedral Complex Pass with Audio Guide (OPA SI PASS)
Siena, San Gimignano, Monteriggioni & Chianti from Florence

Siena, San Gimignano, Monteriggioni & Chianti from Florence

$59
per adult
88% of travellers recommend
Siena, San Gimignano, Monteriggioni & Chianti from Florence
Florence Day Trip: Medieval Villages & Cooking Class

Florence Day Trip: Medieval Villages & Cooking Class

$158
per adult
86% of travellers recommend
Florence Day Trip: Medieval Villages & Cooking Class
See all activities in Castellina in Chianti

Castellina in Chianti Hotel Deals

The Social Hub Florence Lavagnini

The Social Hub Florence Lavagnini

Viale Spartaco Lavagnini 70 72 Florence FI
Fully refundableReserve now, pay when you stay
$93 nightly
$118 total
Aug 30 - Aug 31
Total with taxes and fees
9/10 Wonderful! (1,515 reviews)
"I had a great stay. The staff was very friendly and helpful, the hotel is conveniently located in a quiet sector accessible by public transportation and 10 to 15 minutes walking distance to main attracttions. It has a terrace with an amazing panoramic view of the city, a bar and a swimming pool. ..."

Reviewed on Aug 9, 2026

The Social Hub Florence Lavagnini
Plus Florence - Hostel

Plus Florence - Hostel

Via Santa Caterina D'Alessandria, 15 Florence FI
Fully refundableReserve now, pay when you stay
$81 nightly
$98 total
Aug 17 - Aug 18
Total with taxes and fees
8.6/10 Excellent! (1,009 reviews)
"Wasnt sure what to expect from a hostel but this was great. Triple room with private bathroom was spotlessly clean. Location excellent - 15 mins walk from Firenze SMN train station and the Duomo area. Amenities were great - outdoor pool and bar area was excellent for socialising. Bar prices reasonable. ..."

Reviewed on Aug 6, 2026

Plus Florence - Hostel
Hotel Paris

Hotel Paris

Via Banchi 2 Florence FI
Fully refundableReserve now, pay when you stay
$124 nightly
$150 total
Aug 12 - Aug 13
Total with taxes and fees
9/10 Wonderful! (1,019 reviews)
"Loved this hotel! We had a quad room with a huge fireplace (not active) and a ceiling fresco. Very large room and comfortable. Great breakfast and staff. Assisted us with a reservation at L’Brindellone. Overall probably the best hotel I have stayed in. Easy walking distance to most of the Florence ..."

Reviewed on Aug 9, 2026

Hotel Paris
See all 15,584 properties in Castellina in Chianti
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 Castellina in Chianti Vacation Packages

Castellina in Chianti Essential Information

Language
Italian
Currency
Euros
Local Welcome
Ciao
Local Goodbye
Ciao
Closest Airport
Peretola Airport (FLR)
Population
1,350
Max Temp Winter
50ºF
Max Temp Summer
85ºF
Top Sights
Siena Cathedral, Tenuta Torciano Winery and Monteriggioni Castle

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Frequently asked questions

How much does a Castellina in Chianti vacation package cost?
You can grab a vacation package to this top destination from $2,627 on Expedia. But how much your vacation to Castellina in Chianti costs will depend on your hotel choice, season and length of stay.
What are the cheapest months to go to Castellina in Chianti?
November, December and January are great times to look for cheap Castellina in Chianti vacation packages. Traveling in less busy months means you'll typically find better prices on accommodations and flights.
How many days is enough for Castellina in Chianti?
With about 3 days, you'll have plenty of time to enjoy popular neighborhoods like San Leonino and Villa during your Castellina in Chianti vacation. Be sure to also add Archaeological Museum of Chianti and City Hall Castellina In Chianti to your must-do list. Looking for more adventures? Consider venturing outside of Castellina in Chianti on day trips and tours.
Is it worth booking a vacation package to Castellina in Chianti?
Castellina in Chianti has all the ingredients you need for a memorable trip — dining, nature and walking trails are just the start. Whether you want to visit sights such as Walls of Monteriggioni and Archaeological Museum of Chianti, or venture off the beaten track, you'll have plenty to do on your Castellina in Chianti vacation.
How to find the best Castellina in Chianti package deals?
Start your search for a Castellina in Chianti package deal by entering your preferred trip dates and destination under our "Packages" tab. Then select a few filters, like "Popular locations" and "Property type," to tailor the results to your exact style. You can also sort by "Package discount" and browse offers that come with unbeatable savings. If you don't find the ideal Castellina in Chianti package deal straight away, simply change your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Castellina in Chianti escape underway.
Is it cheaper to book a Castellina in Chianti vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your car rental, flight and hotel into one great-value price and enjoy significant savings. You'll usually get a better deal than booking each component individually. And you'll still enjoy the freedom to create a personalized Castellina in Chianti vacation by choosing your favorite type of stay, airline and car class.
When to book a vacation package to Castellina in Chianti?
If you're planning a spontaneous Castellina in Chianti vacation, browse our last-minute deals that can be booked up to one week before you go. Don't want to leave things to the last minute? You can score amazing deals on your flights and hotels by booking ahead.
How to plan a trip to Castellina in Chianti?
  1. Choose your travel dates: The things you plan to do in Castellina in Chianti and your preferred season will help you decide when to get away.
  2. Set your budget: Factor in costs such as flights, food and transportation when working out how much to put aside for your trip to Castellina in Chianti. Then, choose a property that works with your budget, whether that's an economical stay or a lavish retreat.
  3. Use Expedia's trip planning tool to explore Castellina in Chianti: Research every part of your trip to Castellina in Chianti with this comprehensive planner. Invite your friends and family to collaborate on a group getaway, search for hotels or things to do and make bookings.
  4. Decide your trip length: Consider how much time you'd like to spend discovering Castellina in Chianti. Plan your days so you can get to all the attractions and activities you're interested in at a comfortable pace.
  5. Combine your airfare and accommodations: After you've settled on your trip dates and duration, book the perfect Castellina in Chianti vacation package for you.
  6. Add on experiences and excursions: Have a look at our travel guide to find some awesome things to do in Castellina in Chianti. Book tickets or make reservations as soon as you can to save time and skip the hassle of looking for activities when you arrive.
Does Expedia offer Book Now, Pay Later Castellina in Chianti vacation packages?
Your Castellina in Chianti break should be a relaxing escape from your busy life, not a reason for money worries. So to give you a little more flexibility, we've partnered with online lender Affirm to offer our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and split up the total cost over 3, 6 or 12 months. Plus, there are no late payment fees or hidden costs to worry about.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.