Title: Chianti Region Castles With Overnight Rooms from $80| Expedia.com [Chianti Region Travel Guide](https://expedia.com/Chianti-Region.dx603148)[Hotels in Chianti Region](https://expedia.com/Chianti-Region-Hotels.d603148.Travel-Guide-Hotels)[Vacation Rentals in Chianti Region](https://expedia.com/Chianti-Region-Vacation-Rentals.d603148.Travel-Guide-VacationRentals)[Flights to Chianti Region](https://expedia.com/Cheap-Flights-To-Chianti-Region.d603148.Travel-Guide-Flights)[Things to do in Chianti Region](https://expedia.com/Things-To-Do-In-Chianti-Region.d603148.Travel-Guide-Activities)[Car Rentals in Chianti Region](https://expedia.com/Car-Rentals-In-Chianti-Region.d603148.Car-Rental-Guide)[Chianti Region Vacation Packages](https://expedia.com/Chianti-Region.d603148.Destination-Travel-Guides) ![Chianti Region which includes farmland](https://images.trvl-media.com/place/603148/a6b4be95-df3f-44a2-bf6d-bb1e6f500def.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/603148/a6b4be95-df3f-44a2-bf6d-bb1e6f500def.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light_bundle_and_save.svg) ### Bundle & Save Get more, spend less whenever you see Bundle & Save deals - ![](https://a.travel-assets.com/travel-assets-manager/pictograms-expedia/light__onekey.svg) ### OneKeyCash Earn OneKeyCash on all your eligible bookings - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light_ftc.svg) ### Upfront pricing We are not like the others - we include taxes and fees ## Check prices for these dates Next weekend [Feb 13 - Feb 15](https://www.expedia.com/Hotel-Search?regionId=603148&startDate=2026-02-13&endDate=2026-02-15&adults=2&lodging=CASTLE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Feb 20 - Feb 22](https://www.expedia.com/Hotel-Search?regionId=603148&startDate=2026-02-20&endDate=2026-02-22&adults=2&lodging=CASTLE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Mar 6 - Mar 8](https://www.expedia.com/Hotel-Search?regionId=603148&startDate=2026-03-06&endDate=2026-03-08&adults=2&lodging=CASTLE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Apr 3 - Apr 5](https://www.expedia.com/Hotel-Search?regionId=603148&startDate=2026-04-03&endDate=2026-04-05&adults=2&lodging=CASTLE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Chianti Region castles ![Aerial view](https://images.trvl-media.com/lodging/115000000/114730000/114728600/114728523/50689ae3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/115000000/114730000/114728600/114728523/fb9ce640.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/115000000/114730000/114728600/114728523/cc1d13c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/115000000/114730000/114728600/114728523/c4d4cf02.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Castello Di Montemasso [](https://www.expedia.com/Greve-In-Chianti-Hotels-Castello-Di-Montemasso.h114728523.Hotel-Information) Greve in Chianti 10/10 Exceptional (12 reviews) "Sanja and her husband were amazing hosts. They made sure we had everything we needed. The place was so beautiful and comfortable. We loved it!!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kathleen $125 nightly $139 total Mar 1 - Mar 2 Total with taxes and fees [](https://www.expedia.com/Greve-In-Chianti-Hotels-Castello-Di-Montemasso.h114728523.Hotel-Information) ![Standard Triple Room | Hypo-allergenic bedding, down comforters, desk, soundproofing](https://images.trvl-media.com/lodging/108000000/107200000/107195900/107195877/8df84232.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/108000000/107200000/107195900/107195877/108d1b99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/108000000/107200000/107195900/107195877/0390d01b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/108000000/107200000/107195900/107195877/51882a03.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cattaleya Rooms [](https://www.expedia.com/Florence-Hotels-HOSTEL-SANTA-MARIA-NOVELLA.h107195877.Hotel-Information) Santa Maria Novella 8.4/10 Very Good (37 reviews) "Had a 2 night stayover in Firenze, and thanks to the good location, we only had a small walk to the city centre. Great value for parking at the Apcoa underground park, 10€ for 24h!! " ![Germany](https://a.travel-assets.com/egds/marks/flags/de.svg) Metin $59 nightly $80 total Feb 6 - Feb 7 Total with taxes and fees [](https://www.expedia.com/Florence-Hotels-HOSTEL-SANTA-MARIA-NOVELLA.h107195877.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/105000000/104780000/104774800/104774707/b1eba8b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/105000000/104780000/104774800/104774707/e1152786.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/105000000/104780000/104774800/104774707/18ff7255.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/105000000/104780000/104774800/104774707/312cdebd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Torre Sassa - Torre Medievale in Toscana [](https://www.expedia.com/Montecatini-Val-Di-Cecina-Hotels-Torre-Sassa-Torre-Medievale-In-Toscana.h104774707.Hotel-Information) Sassa 10/10 Exceptional (1 review) "This tower was absolutely beautiful, spacious and clean. The medieval decor was awesome. Stefania came in to cook and it was absolutely amazing and delicious. We left some items behind and Giacomo contacted us promptly and is shipping the items back home to us. An absolutely wonderful experience!!" ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Cindylou $739 nightly $742 total Feb 6 - Feb 7 Total with taxes and fees [](https://www.expedia.com/Montecatini-Val-Di-Cecina-Hotels-Torre-Sassa-Torre-Medievale-In-Toscana.h104774707.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/40000000/39140000/39138500/39138427/a75024ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/40000000/39140000/39138500/39138427/beec271a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/40000000/39140000/39138500/39138427/14ab515a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/40000000/39140000/39138500/39138427/d30c34da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### CASTELLO NELLE CRETE [](https://www.expedia.com/Asciano-Hotels-CASTELLO-NELLE-CRETE.h39138427.Hotel-Information) Siena 10/10 Exceptional (1 review) "Picture yourself in a century-old castle high on a hill in the heart of Tuscany. Your surroundings are those of a majestic Monet painting. Birds humming, and the smell of fresh croissants fills the air. A cup of hot cappucino is being brought to you by the most professional but always smiling and always friendly staff .No you're not dreaming, you and your family of 30 are guests at Villa Leonina, Every room has an ensuite bathroom with daily maintenance and fresh towels. The kitchen and... ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) joanne s. $18,258 nightly $18,258 total Feb 6 - Feb 7 Total with taxes and fees [](https://www.expedia.com/Asciano-Hotels-CASTELLO-NELLE-CRETE.h39138427.Hotel-Information) 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. [View all properties](https://expedia.com/Hotel-Search?startDate=2026-02-19&endDate=2026-02-20®ionId=603148&adults=2&lodging=CASTLE&sort=RECOMMENDED&openPlayBack=true) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in ](https://expedia.com/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FChianti-Region-Castles.d603148-aaCastles.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.com/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FChianti-Region-Castles.d603148-aaCastles.Travel-Guide-Accommodation) ## Top Chianti Region Hotel Reviews ![Hotel Palazzo San Lorenzo & SPA](https://images.trvl-media.com/lodging/4000000/3480000/3475000/3474921/1af45070_y.jpg) ### Hotel Palazzo San Lorenzo & SPA 10/10 Excellent "Very good place, clean, good service, great food, the rooms were amazing." [](https://expedia.com/Colle-Di-Val-DElsa-Hotels-Hotel-Palazzo-San-Lorenzo-SPA.h3474921.Hotel-Information) ![Villa Casagrande Resort & SPA](https://images.trvl-media.com/lodging/1000000/900000/891700/891661/f41faf16_y.jpg) ### Villa Casagrande Resort & SPA 10/10 Excellent "Always beautiful when I stay here, staff are helpful and every room clean and tidy " [](https://expedia.com/Figline-E-Incisa-Valdarno-Hotels-Villa-Casagrande-Resort-SPA.h891661.Hotel-Information) ![Hotel Borgo di Cortefreda Relais](https://images.trvl-media.com/lodging/2000000/1220000/1216500/1216478/288cff0c_y.jpg) ### Hotel Borgo di Cortefreda Relais 10/10 Excellent "The hotel and services exceeded my expectations." [](https://expedia.com/Barberino-Tavarnelle-Hotels-Hotel-Borgo-Di-Cortefreda-Relais.h1216478.Hotel-Information) ![Hotel Toscana Ambassador](https://images.trvl-media.com/lodging/2000000/1430000/1429500/1429488/7717f75b_y.jpg) ### Hotel Toscana Ambassador 10/10 Excellent "We recommend the Toscana Ambassador to everyone, as we had a great experience with its cleanliness, hospitality, friendliness, and an extraordinary breakfast, with excellent service from Ada & Julia and the rest of the crew, from the front desk to room service. If you ever visit Poggibonsi, Tuscany, stay here with no hesitation. " [](https://expedia.com/Poggibonsi-Hotels-Hotel-Toscana-Ambassador.h1429488.Hotel-Information) ![Salvadonica - Borgo del Chianti](https://images.trvl-media.com/lodging/21000000/20490000/20484000/20483959/56ce48bb_y.jpg) ### Salvadonica - Borgo del Chianti 10/10 Excellent "Great staff, great room and amenities. Outstanding romantic Tuscany location. Going back again." [](https://expedia.com/San-Casciano-In-Val-Di-Pesa-Hotels-Salvadonica.h20483959.Hotel-Information) ![Agriturismo San Sano](https://images.trvl-media.com/lodging/2000000/1500000/1492000/1491964/f2375def_y.jpg) ### Agriturismo San Sano 10/10 Excellent "You can never go wrong in Toscana , even in off season . San Sano even more so, hidden from mass tourism. " [](https://expedia.com/Gaiole-In-Chianti-Hotels-Hotel-Residence-San-Sano.h1491964.Hotel-Information) ![Castello Vicchiomaggio](https://images.trvl-media.com/lodging/8000000/7570000/7564900/7564854/3167b59e_y.jpg) ### Castello Vicchiomaggio 10/10 Excellent "This beautiful property stole our hearts back in 2019, when my now-wife first visited this magical place. Six years later, we returned — this time to celebrate our wedding reception after tying the knot a few months earlier. From start to finish, everything was beyond wonderful. A special mention to Sandra, the amazing coordinator who made everything run so smoothly, and her fantastic team — Delfina and the lovely lady (whose name, unfortunately, I’ve forgotten) who graciously welcomed and ushered our guests upon arrival. Every detail was handled with care and professionalism. The food and Chianti wines during our celebration were absolutely exceptional — truly a highlight that everyone still talks about! The breakfast and dinner staff were attentive, kind, and ensured everything was perfect throughout our stay. Our rooms were clean, comfortable, and beautifully maintained, with housekeeping doing a fantastic job. We also had the privilege of meeting Mr. John Matta, the owner — such a gracious and inspiring man who leads an extraordinary team. All of our guests loved their stay, and we left with hearts full of joy and gratitude. We can’t wait to come back again — hopefully for our anniversary next time." [](https://expedia.com/Greve-In-Chianti-Hotels-Castello-Vicchiomaggio.h7564854.Hotel-Information) ![COMO Castello Del Nero](https://images.trvl-media.com/lodging/2000000/1280000/1279800/1279768/5908bcb2_y.jpg) ### COMO Castello Del Nero 10/10 Excellent "Wonderful stay. 5-stars across the board if you’re looking for disconnecting and relaxing in the rolling hills of the Tuscan countryside. Easy day/dinner trips to Florence or Siena (rental car). " [](https://expedia.com/Barberino-Tavarnelle-Hotels-COMO-Castello-Del-Nero.h1279768.Hotel-Information) ![Il Borro - Relais & Châteaux](https://images.trvl-media.com/lodging/6000000/5590000/5585700/5585638/4a6bd899_y.jpg) ### Il Borro - Relais & Châteaux 10/10 Excellent "A one of a kind, unique property amazing cuisine, and the tour we took of the wine cellar was the best I have ever experienced thanks to the helpfulness and knowledge of our guide Sophia" [](https://expedia.com/Loro-Ciuffenna-Hotels-Il-Borro-Relais-Chateaux.h5585638.Hotel-Information) ## Find out more about Chianti Region ## Chianti Region Castles information | Number of reviews | 50 | | ----------------- | ---------- | | Accommodation | 48 Castles | | Lowest Price | $80 | | Highest Price | $18,258 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - Other - More ways to book - [Hotels near Borgo di Vescine - Tenute di Castelvecchi ](https://www.expedia.com/Borgo-Di-Vescine-Tenute-Di-Castelvecchi-Hotels.0-l553248621532500717-0.Travel-Guide-Filter-Hotels) - 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