Title: Castellina in Chianti Vacation Packages 2026 from $833 | 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 $833 ## 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/29000000/28970000/28962000/28961941/26fd50f1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Aurum Firenze Historic Centre of Florence Save 100% on your flight $833 per person Apr 16 - Apr 21 found 1 day ago Roundtrip flight included Boston (BOS) to Florence (FLR) 7.6/10 Good! (1,002 reviews) 9 day stay. The property hit my must-haves! Central location, clean, affordable, and safe. 5/5 in all these areas! There is nothing they can do about dirty streets but the filth did not cross the threshold. T2 tram from the airport is 2 blocks away. The central market is 2 blocks in the other direction. Key card swipe after dark. 24 hour desk service. Breakfast on the 5th floor with views. Very courteous staff. The only complaint is breakfast tables are cleared very quickly while I went for a americano refill. Will definitely return here. Reviewed on Jan 3, 2026 ![Aurum Uffizi](https://images.trvl-media.com/lodging/3000000/2550000/2541700/2541615/862ad26c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Aurum Uffizi Historic Centre of Florence Save 100% on your flight $845 per person Apr 16 - Apr 21 found 1 day ago Roundtrip flight included Boston (BOS) to Florence (FLR) 7.8/10 Good! (1,000 reviews) This is not a typical hotel where there is a lobby or staff to greet you . Instead it is a set of apartments in a corner building . The person who let us in was awaiting for us at the door at check in. Breakfast was serve in a buffet style . Staff would ask if you would order something else if you like. Continental breakfast is available .Overall it was comfortable and easy to find . Shops and restaurants are all walking distance. Reviewed on Jan 15, 2026 ![Eurostars Florence Boutique](https://images.trvl-media.com/lodging/2000000/1170000/1167000/1166901/10f2f159_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Eurostars Florence Boutique Historic Centre of Florence Save 100% on your flight $978 per person Apr 16 - Apr 21 found 1 day ago Roundtrip flight included Boston (BOS) to Florence (FLR) 8.6/10 Excellent! (476 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 ![Hotel Duomo Firenze](https://images.trvl-media.com/lodging/3000000/2550000/2541700/2541603/fdd7cf48_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Duomo Firenze Historic Centre of Florence Save 100% on your flight $1,368 per person Apr 16 - Apr 21 found 1 day ago Roundtrip flight included Boston (BOS) to Florence (FLR) 9.2/10 Wonderful! (1,002 reviews) Friendly staff, clean room, good location. Reviewed on Jan 25, 2026 ![The Moon Boutique Hotel & Spa](https://images.trvl-media.com/lodging/23000000/22260000/22255000/22254976/205f9600_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Moon Boutique Hotel & Spa Historic Centre of Florence Save 100% on your flight $1,221 per person Apr 16 - Apr 21 found 1 day ago Roundtrip flight included Boston (BOS) to Florence (FLR) 9.6/10 Exceptional! (495 reviews) The spa was wonderful though the jacuzzi could be hotter I think! The only complaint was that the bed wasn’t very comfortable (it was pretty hard) and the pillows were rather flat. Reviewed on Jan 2, 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/2026-03-05/2026-03-12/?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 romantic area. [](https://expedia.com/Buondonno-Winery-Castellina-in-Chianti.d553248635823420151.Vacation-Attraction) #### City Hall Castellina In Chianti 5/5(1 review) 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 wineries in this quaint area. [](https://expedia.com/City-Hall-Castellina-In-Chianti-Castellina-in-Chianti.d553248635175258965.Vacation-Attraction) #### Archaeological Museum of Chianti 4/5(1 review) 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. [](https://expedia.com/Archaeological-Museum-Of-Chianti-Castellina-in-Chianti.d553248621533001050.Vacation-Attraction) ### What to do in Castellina in Chianti ![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 $61 per adult **88%** of travellers recommend [](https://expedia.com/things-to-do/siena.a553041.activity-details) ![Florence Day Trip: Medieval Villages & Cooking Class](https://mediaim.expedia.com/localexpert/321506/1e2813e3-17ae-4ee9-bf76-f82b70d58df9.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Florence Day Trip: Medieval Villages & Cooking Class $162 per adult **86%** of travellers recommend [](https://expedia.com/things-to-do/florence-day-trip-medieval-villages-cooking-class.a321506.activity-details) ![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 $48 per adult **88%** of travellers recommend [](https://expedia.com/things-to-do/chianti-half-day-wine-tour-from-florence.a510796.activity-details) [See all activities in Castellina in Chianti](https://expedia.com/things-to-do/search?rid=55534) ## Castellina in Chianti Hotel Deals ![c-hotels Ambasciatori](https://images.trvl-media.com/lodging/1000000/10000/1900/1829/bddb8fbc_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### c-hotels Ambasciatori Via Luigi Alamanni 3 Florence FI $89 nightly $114 total Feb 22 - Feb 23 Total with taxes and fees 8.2/10 Very Good! (1,002 reviews) Great location, short walk to the Duomo, museums and shopping. A clean quiet room awaited me. Reviewed on Jan 21, 2026 [](https://expedia.com/Hotel-Search?startDate=2%2F22%2F2026&endDate=2%2F23%2F2026&selected=1829&PinnedHotelID=1829&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 $95 nightly $122 total Feb 9 - Feb 10 Total with taxes and fees 9.6/10 Exceptional! (1,133 reviews) Fantastic service, exceptionallly clean room, free drink and minibar was a nice addition. Highly recommend. Lovely coming home after a day sightseeing. Reviewed on Feb 1, 2026 [](https://expedia.com/Hotel-Search?startDate=2%2F9%2F2026&endDate=2%2F10%2F2026&selected=89035039&PinnedHotelID=89035039&HadPinnedHotel=true®ionId=55534) ![Bernini Palace](https://images.trvl-media.com/lodging/1000000/20000/14000/13999/84743cc7_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Bernini Palace Piazza San Firenze 29 Florence FI Fully refundableReserve now, pay when you stay $235 nightly $277 total Feb 19 - Feb 20 Total with taxes and fees 9.6/10 Exceptional! (1,003 reviews) Staff very helpful Rooms very clean Good breakfast options Reviewed on Jan 30, 2026 [](https://expedia.com/Hotel-Search?startDate=2%2F19%2F2026&endDate=2%2F20%2F2026&selected=13999&PinnedHotelID=13999&HadPinnedHotel=true®ionId=55534) [See all 15,004 properties in Castellina in Chianti](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=2%2F6%2F2026&endDate=2%2F7%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). 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