Title: Castellina in Chianti Vacation Packages 2026 from $1,274 | Expedia.com [Castellina in Chianti Travel Guide](https://expedia.com/Castellina-In-Chianti.dx55534)[Hotels in Castellina in Chianti](https://expedia.com/Castellina-In-Chianti-Hotels.d55534.Travel-Guide-Hotels)[Vacation Rentals in Castellina in Chianti](https://expedia.com/Castellina-In-Chianti-Vacation-Rentals.d55534.Travel-Guide-VacationRentals)[Flights to Castellina in Chianti](https://expedia.com/Cheap-Flights-To-Castellina-In-Chianti.d55534.Travel-Guide-Flights)[Things to do in Castellina in Chianti](https://expedia.com/Things-To-Do-In-Castellina-In-Chianti.d55534.Travel-Guide-Activities)[Car Rentals in Castellina in Chianti](https://expedia.com/Car-Rentals-In-Castellina-In-Chianti.d55534.Car-Rental-Guide) ![](https://images.trvl-media.com/place/55534/68deebc9-9310-492d-8f83-85d906ba54aa.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Castellina in Chianti Vacations from $1,274 ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to $1,045 when you book a flight and hotel together\* - ### Find the right fit With over 300,000 hotels worldwide, it's easy to create a perfect package - ### Rest easy Plan, 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](https://www.expedia.com/Isole-E-Olena-Winery-Barberino-Tavarnelle.d6230534.Vacation-Attraction), [Il Molino di Grace Winery](https://www.expedia.com/Il-Molino-Di-Grace-Winery-Greve-in-Chianti.d6333570.Vacation-Attraction) and [Castello di Radda Winery](https://www.expedia.com/Castello-Di-Radda-Winery-Radda-in-Chianti.d553248621532501476.Vacation-Attraction). 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. ![Aurum Firenze](https://images.trvl-media.com/lodging/29000000/28970000/28962000/28961941/3c6602ae_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Aurum Firenze Historic Centre of Florence $1,274 per person May 31 - Jun 5 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to Florence (FLR) 7.6/10 Good! (1,008 reviews) Only Shampoo, no body wash. Oragen juice dispenser spits water. Way too many noise and fights on the street. Reviewed on Mar 21, 2026 ![Aurum Uffizi](https://images.trvl-media.com/lodging/3000000/2550000/2541700/2541615/4fb74083_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Aurum Uffizi Historic Centre of Florence Save 100% on your flight $1,582 per person May 9 - May 15 found 1 day ago Roundtrip non-stop flight included New York (NYC) to Florence (FLR) 7.6/10 Good! (1,002 reviews) Great location, but on a noisy alley. Reviewed on Mar 20, 2026 ![Eurostars Florence Boutique](https://images.trvl-media.com/lodging/2000000/1170000/1167000/1166901/88283612_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Eurostars Florence Boutique Historic Centre of Florence $1,663 per person May 17 - May 22 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to Florence (FLR) 8.6/10 Excellent! (483 reviews) The room was clean and the staff very accommodating. The breakfast was quite sufficient and had a good variety. The location is great. It's a short walk from the square, shopping and from restaurants. Reviewed on Dec 13, 2025 ![The Moon Boutique Hotel & Spa](https://images.trvl-media.com/lodging/23000000/22260000/22255000/22254976/a69619e4_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Moon Boutique Hotel & Spa Historic Centre of Florence Save 100% on your flight $2,128 per person Jun 15 - Jun 20 found 1 day ago Roundtrip flight included Boston (BOS) to Florence (FLR) 9.6/10 Exceptional! (512 reviews) Staff excellent, room very good, food good. Facilities and location all good. Would be happy return and to recommend to family and friends. Thank you for such a pleasant stay Reviewed on Mar 17, 2026 ![Hotel La Scaletta Al Ponte Vecchio](https://images.trvl-media.com/lodging/2000000/1610000/1604300/1604285/d1c916cb_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel La Scaletta Al Ponte Vecchio Historic Centre of Florence Save 100% on your flight $2,230 per person May 7 - May 13 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to Florence (FLR) 8.8/10 Excellent! (971 reviews) There were no Vineyard views but it is in a decent location in Florence. The "Garden Suite" is a joke. It overlooks a courtyard that was covered in green moss and had a hose strewed about. It was not usable. So there was no view of anything. We opened the window overlooking it at night to get some air and I assume this is why we woke up with lots of bites! We never saw a mosquito though. They told us the AC didn't work. The hotel's elevator is a 1 person elevator that was too scary to use really. Our room was on the seventh floor. The staff did help with bringing the luggage up but if you don't like to climb MANY stairs, this is not the place for you. We tried to upgrade to a third person and this caused quite the comotion and really I feel they charged us in excess by making us upgrade to a suite and then charged more per person. They blamed a communication error but that was really not it! One desk person tried to make it right and was very nice but really in the end fell short. The suite was spacious and nice but the glass shelf in it had not been dusted in quite some time. It had a soaking tub, steam room and sauna, although the sauna and steam room did not work. The rooftop bar has a nice view but it is a workout to get up there! It's also where they serve breakfast and where the workout room is. I would not recommend this hotel. Reviewed on Mar 17, 2026 Don't see what you're looking for? See all available trips from Columbus to Castellina in Chianti [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-04-23/2026-04-30/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=FLR&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ### Discover the most popular places to visit in Castellina in Chianti ![Castellina in Chianti which includes farmland](https://images.trvl-media.com/place/553248635823420151/ee82ec03-289c-48c5-8d68-58e0a551a93c.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Buondonno Winery 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 quaint area. [](https://expedia.com/Buondonno-Winery-Castellina-in-Chianti.d553248635823420151.Vacation-Attraction) #### City Hall Castellina In Chianti City Hall Castellina In Chianti is just one of the places to see in Castellina in Chianti, so why not enjoy the other things to explore during your travels? Discover the beautiful countryside and charming coffeehouses in this walkable area. [](https://expedia.com/City-Hall-Castellina-In-Chianti-Castellina-in-Chianti.d553248635175258965.Vacation-Attraction) #### Casa Vinicola Luigi Cecchi 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. [](https://expedia.com/Casa-Vinicola-Luigi-Cecchi-Castellina-in-Chianti.d6103262.Vacation-Attraction) ### What to do in Castellina in Chianti ![Chianti Half Day Wine Tour from Florence](https://mediaim.expedia.com/localexpert/510796/711ec9bb-4d40-40e5-a110-59519c36ce6d.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Chianti Half Day Wine Tour from Florence $58 per adult **88%** of travellers recommend [](https://expedia.com/things-to-do/chianti-half-day-wine-tour-from-florence.a510796.activity-details) ![Siena, San Gimignano, Monteriggioni & Chianti from Florence](https://mediaim.expedia.com/localexpert/553041/def47daa-d183-43ae-81a6-3355ec60f5c9.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Siena, San Gimignano, Monteriggioni & Chianti from Florence $77 per adult **86%** of travellers recommend [](https://expedia.com/things-to-do/siena.a553041.activity-details) ![Monteriggioni fortress](https://mediaim.expedia.com/localexpert/1139505/e7076e74-fe99-4b02-a9fc-f527a478919b.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Tuscany Hiking Tour from Siena Including Wine Tasting $71 per adult [](https://expedia.com/things-to-do/tuscany-hiking-tour-from-siena-including-wine-tasting.a1139505.activity-details) [See all activities in Castellina in Chianti](https://expedia.com/things-to-do/search?rid=55534) ## Castellina in Chianti Hotel Deals ![Hotel Machiavelli Palace](https://images.trvl-media.com/lodging/1000000/530000/521300/521248/ab2b96dc_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hotel Machiavelli Palace Via Nazionale 10 Florence FI Fully refundableReserve now, pay when you stay $89 nightly $112 total Mar 29 - Mar 30 Total with taxes and fees 8.4/10 Very Good! (170 reviews) was so perfect! Reviewed on Mar 10, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F29%2F2026&endDate=3%2F30%2F2026&selected=521248&PinnedHotelID=521248&HadPinnedHotel=true®ionId=55534) ![IQ Hotel Firenze](https://images.trvl-media.com/lodging/90000000/89040000/89035100/89035039/72f32f77_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### IQ Hotel Firenze Via Camillo Cavour, 88 Florence FI Fully refundableReserve now, pay when you stay $158 nightly $190 total Mar 29 - Mar 30 Total with taxes and fees 9.6/10 Exceptional! (1,194 reviews) Wonderful! Reviewed on Mar 20, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F29%2F2026&endDate=3%2F30%2F2026&selected=89035039&PinnedHotelID=89035039&HadPinnedHotel=true®ionId=55534) ![The Social Hub Florence Lavagnini](https://images.trvl-media.com/lodging/24000000/23200000/23198300/23198289/fdc60d68_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Social Hub Florence Lavagnini Viale Spartaco Lavagnini 70 72 Florence FI Fully refundableReserve now, pay when you stay $119 nightly $148 total Mar 29 - Mar 30 Total with taxes and fees 9/10 Wonderful! (1,318 reviews) Great Reviewed on Mar 20, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F29%2F2026&endDate=3%2F30%2F2026&selected=23198289&PinnedHotelID=23198289&HadPinnedHotel=true®ionId=55534) [See all 15,270 properties in Castellina in Chianti](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=3%2F24%2F2026&endDate=3%2F25%2F2026®ionId=55534) 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](https://www.expedia.com/Siena-Cathedral-Siena-Historical-Center.d6077922.Vacation-Attraction), [Tenuta Torciano Winery](https://www.expedia.com/Tenuta-Torciano-Winery-San-Gimignano.d6252546.Vacation-Attraction) and [Monteriggioni Castle](https://www.expedia.com/Monteriggioni-Castle-Monteriggioni.d6258231.Vacation-Attraction) | ## More vacations you might like ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations [](https://expedia.com/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations [](https://expedia.com/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Kid Friendly Vacations [](https://expedia.com/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Kid_Friendly%20Vacations.click) 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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](https://www.expedia.com/why/trip-planning) 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](https://www.expedia.com/Things-To-Do-In-Castellina-In-Chianti.d55534.Travel-Guide-Activities). 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? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - More ways to book - [Hotels near Montecalvario ](https://www.expedia.com/Montecalvario-Hotels.0-l553248621533001049-0.Travel-Guide-Filter-Hotels) - [Villas in Cavallari ](https://www.expedia.com/Cavallari-Villas.d553248622858908079-aaVillas.Travel-Guide-Accommodation) - [B&B in Cavallari ](https://www.expedia.com/Cavallari-Bed-And-Breakfast.d553248622858908079-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Cavallari Hotels ](https://www.expedia.com/Cavallari-Hotels.d553248622858908079.Travel-Guide-Hotels) - [Resorts in Cavallari ](https://www.expedia.com/Cavallari-Resorts.d553248622858908079-aaResorts.Travel-Guide-Accommodation) - [Gay friendly Hotels in Colle Petroso ](https://www.expedia.com/Colle-Petroso-Hotels-LGBT-Welcoming-Hotel.0-0-d553248622858970030-tLGBTWelcomingHotel.Travel-Guide-Filter-Hotels) - 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[Things to do in Radda in Chianti ](https://www.expedia.com/Things-To-Do-In-Radda-In-Chianti.d601693.Travel-Guide-Activities) - [Things to do in Panzano in Chianti ](https://www.expedia.com/Things-To-Do-In-Panzano-In-Chianti.d602564.Travel-Guide-Activities) \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.