Castellina in Chianti Vacations from $884
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $2,000 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
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.
The Moon Boutique Hotel & Spa
Historic Centre of Florence
$884
per person
Dec 1 - Dec 6
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9.6/10 Exceptional! (592 reviews)
Great location. We suggest taking the river down to the city center every day. The free breakfast and coffee is great way to start your day. Schedule a spa day at least once so you can relax before the walk to dinner! Reception was super nice and even helped us call a taxi.
Reviewed on Sep 21, 2026
Relais Uffizi, Tailor made Hotel
Historic Centre of Florence
$2,047
per person
Oct 24 - Oct 31
found 13 hours ago
Roundtrip flight included
New York (LGA) to Florence (FLR)
9.2/10 Wonderful! (161 reviews)
LOVE this hotel! Perfect location, amazing breakfast, fantastic staff, beautiful rooms, excellent bathrooms. Made our Florence trip amazing highlight of our time in Italy!
Reviewed on Sep 15, 2026
Hotel La Scaletta Al Ponte Vecchio
Historic Centre of Florence
$941
per person
Dec 1 - Dec 6
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9/10 Wonderful! (1,005 reviews)
The hotel is in a centrally located area with very close proximity (walking) to major museums and shopping with no need for a car.
Room was fairly clean but it seems long overdue for an update.
Breakfast fee is €10 per day which is very reasonable with many choices of hot and cold items.
The staff are very helpful and friendly and that is a great asset to the hotel.
Reviewed on Sep 22, 2026
Hotel Duomo Firenze
Historic Centre of Florence
$980
per person
Dec 1 - Dec 6
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9.2/10 Wonderful! (1,001 reviews)
The location of this hotel is excellent in central Florence in a pedestrian only street steps across from the Duomo. Walkable to everything for choice of restaurants and shops. The staff was outstanding and the breakfast choices were very good and better than going to a cafe nearby. The room had great storage and the bathroom was renovated very nicely. The hotel is on the 4th floor of a historial building and has an elevator.
Reviewed on Sep 23, 2026
Don't see what you're looking for?
See all available trips from Columbus to Castellina in Chianti
View all tripsStay 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.
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 walkable area, or enjoy its local tours.
Lilliano Estate Winery
You can enjoy a tasting or tour at Lilliano Estate Winery during your travels to Lilliano.
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 relaxing area.
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.
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.
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.
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.
What to do in Castellina in Chianti
Siena, San Gimignano, Monteriggioni & Chianti from Florence
$61
per adult
88% of travellers recommend
From Siena: Chianti and Castles Tour with Wine Tastings
$99
per adult
88% of travellers recommend
Florence Day Trip: Medieval Villages & Cooking Class
$185
per adult
86% of travellers recommend
Castellina in Chianti Hotel Deals
Plus Florence - Hostel
Via Santa Caterina D'Alessandria, 15 Florence FI
Fully refundableReserve now, pay when you stay
$119 nightly
$140 total
Oct 5 - Oct 6
Total with taxes and fees
8.6/10 Excellent! (1,005 reviews)
"Recommend you experience the two breakfast options available on site. No discount if you pay in advance. Make sure you ask the front desk how to use the washer and dryer."
Reviewed on Sep 20, 2026
The Social Hub Florence Belfiore
Viale Belfiore, 55 Florence FI
Fully refundableReserve now, pay when you stay
$164 nightly
$197 total
Oct 18 - Oct 19
Total with taxes and fees
9.4/10 Exceptional! (745 reviews)
"Clean room tran near by"
Reviewed on Sep 23, 2026
The Social Hub Florence Lavagnini
Viale Spartaco Lavagnini 70 72 Florence FI
Fully refundableReserve now, pay when you stay
$168 nightly
$201 total
Oct 18 - Oct 19
Total with taxes and fees
9/10 Wonderful! (1,588 reviews)
"The building reeks of second hand smoke. You can close your window but the smoke is still in the rooms and corridors. I brought this up to the front desk and they told me they would send someone to “look into it”. Nothing actually happened. The rooms and corridors were very dirty."
Reviewed on Sep 23, 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.
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 |
More vacations you might like
Frequently asked questions
How much does a Castellina in Chianti vacation package cost?
You can grab a vacation package to this top destination from $884 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?
- 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.
- 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.
- 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.
- 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.
- 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.
- 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.
Explore a world of travel with Expedia
- Winery in Castellina in Chianti
- Hotels in Castellina in Chianti
- Villas in Castellina in Chianti
- Hotels in Panzano in Chianti
- Pool in Castellina in Chianti
- Hotels in Poggibonsi
- Privatevacationhomes in Radda in Chianti
- Independent Hotels in Chianti Region
- 5 Star Hotels in Castellina in Chianti
- Hotels in Greve in Chianti
- Hotels in Radda in Chianti
- Bedandbreakfast in Castellina in Chianti
- Relais & Chateaux Hotels in Chianti Region
- 4 Star Hotels in Castellina in Chianti
- Chianti Region All Inclusive Vacation Packages
- Where to stay in Siena
- Visit Monteriggioni
- Chianti Region All Inclusive Vacation Packages
- Visit San Donato in Poggio
- Chianti Region All Inclusive Vacation Packages
- Monsanto Vacations
- Val d'Elsa All Inclusive Vacation Packages
- Where to stay in Chianti Region
- Visit Chianti Region
- Chianti Region All Inclusive Vacation Packages
- Visit Panzano in Chianti
- Chianti Region All Inclusive Vacation Packages
- Radda in Chianti Vacations
- Chianti Region All Inclusive Vacation Packages
- Siena Vacations
- Visit Gaiole in Chianti
- Visit Radda in Chianti
- Chianti Region All Inclusive Vacation Packages
- Visit Castellina in Chianti
- San Gimignano Vacations
- Greve in Chianti Vacations
- Visit Vagliagli
- Chianti Region All Inclusive Vacation Packages
- Panzano in Chianti Vacations
- Casa Sola - Chianti Winery
- Where to stay in Empolese Val d'Elsa
- Buondonno Winery
- Chianti Region All Inclusive Vacation Packages
- Visit Quercegrossa
- Monteriggioni Vacations
- Chianti Region All Inclusive Vacation Packages
- Where to stay in Florence
- Isole e Olena Winery
- Visit Colle di Val d'Elsa
- Visit Greve in Chianti
- Visit Poggibonsi
- Historic Centre of Florence Vacations
- Chianti Region All Inclusive Vacation Packages
- Casa Emma
- Visit Castellina Scalo
- Poggibonsi Vacations
- Where to stay in Val d'Elsa
- Chianti Region All Inclusive Vacation Packages
- Van Car Rentals in Siena
- Car rentals in Castellina in Chianti
- Compact Car Rentals in Castellina in Chianti
- Enterprise Rental Cars in Castellina in Chianti
- Car rentals in Panzano in Chianti
- Car rentals in Poggibonsi
- Car rentals in Radda in Chianti
- Hertz Rental Cars in Castellina in Chianti
- Convertible Car Rentals in Siena
- Car rentals in Lucarelli
- Things to do in Montefioralle
- Things to do in Barberino Tavarnelle
- Things to do in Greve in Chianti
- Things to do in Volpaia
- Things to do in Poggibonsi
- Things to do in Chianti Region
- Things to do in Panzano in Chianti
- Things to do in Gaiole in Chianti
- Things to do in Castellina in Chianti
- Things to do in Colle di Val d'Elsa
- Things to do in Radda in Chianti
- Things to do in Siena
- Things to do in Lecchi in Chianti
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
