Title: Castellina in Chianti Vacation Packages 2026 from $1,121 | 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 $1,121 ## 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. ![Residenza Florentia](https://images.trvl-media.com/lodging/2000000/1140000/1133600/1133528/da5e2175_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Residenza Florentia Historic Centre of Florence $1,121 per person Apr 27 - May 1 found 1 day ago Roundtrip non-stop flight included New York (NYC) to Florence (FLR) 8.6/10 Excellent! (47 reviews) Location, accommodations, and communication. Simple but comfortable. A basic facilities, and nice AC, elevator, and luggage storage. Reviewed on Jun 12, 2025 ![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 $1,150 per person Apr 27 - May 1 found 1 day ago Roundtrip non-stop flight included New York (NYC) to Florence (FLR) 7.6/10 Good! (1,002 reviews) The location is great. Free breakfast was provided and in my opinion it was a good one. Staff is very nice and helpful. Reviewed on Mar 9, 2026 ![Maxim Axial](https://images.trvl-media.com/lodging/3000000/2540000/2532900/2532899/b9927c89_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Maxim Axial Historic Centre of Florence Save 100% on your flight $1,896 per person May 6 - May 12 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to Florence (FLR) 8.6/10 Excellent! (1,005 reviews) Great location and wonderful room! Will book again! Reviewed on Mar 6, 2026 ![Grand Hotel Cavour](https://images.trvl-media.com/lodging/1000000/20000/11000/10993/98a31a3a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Grand Hotel Cavour Historic Centre of Florence Save 100% on your flight $2,062 per person May 6 - May 12 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to Florence (FLR) 9.2/10 Wonderful! (1,000 reviews) Great hotel near the center. Walking distance to everything. I enjoyed the quality of the hotel and the roof top bar was amazing. Good service. Rooms were a little small but not sure if that was because of my budget or whether the hotel rooms were just smaller due to the type/age of the building. All in all I would recommend and most of your time is spent outdoors anyway. Reviewed on Mar 3, 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 $1,882 per person May 6 - May 12 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to Florence (FLR) 8.8/10 Excellent! (967 reviews) Fantastic location for everything whilst not being in the middle of it all. The staff were all lovely and everything super clean. Only issue was the aircon didn't work and we couldn’t open the windows due to mosquitoes (discovered this after the first night with it open - didn’t make that mistake again!). It’s quite an unusual interior with a tiny lift and lots of stairs so just be aware of that - it didn’t bother us though, we loved the charm. Reviewed on Mar 12, 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/2026-04-13/2026-04-20/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=FLR&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.com/deals?rfrr=PKG_SPRING_PROMO_55534) ### 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) ![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 $164 per adult **86%** of travellers recommend [](https://expedia.com/things-to-do/florence-day-trip-medieval-villages-cooking-class.a321506.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 $90 nightly $113 total Mar 16 - Mar 17 Total with taxes and fees 8.4/10 Very Good! (169 reviews) was so perfect! Reviewed on Mar 10, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F16%2F2026&endDate=3%2F17%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 $120 nightly $149 total Mar 16 - Mar 17 Total with taxes and fees 9.6/10 Exceptional! (1,192 reviews) The staff really made the difference. It was our son’s birthday during our stay. We didn’t tell them but I guess they saw it on his passport when we checked in. While we were having breakfast, they brought a special treat to our son to celebrate this special day. It was a really nice gesture and ... Reviewed on Mar 13, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F16%2F2026&endDate=3%2F17%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 $101 nightly $127 total Mar 15 - Mar 16 Total with taxes and fees 9/10 Wonderful! (1,317 reviews) The hotel was really nice and so many spots where you can work! The location was great - I’ll definitely come back. Reviewed on Mar 10, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F15%2F2026&endDate=3%2F16%2F2026&selected=23198289&PinnedHotelID=23198289&HadPinnedHotel=true®ionId=55534) [See all 15,273 properties in Castellina in Chianti](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=3%2F14%2F2026&endDate=3%2F15%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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