Title: Book the Best Chianti Region WINERY Hotels in 2025 | Expedia.ca [Chianti Region Travel Guide](https://expedia.ca/Chianti-Region.dx603148)[Hotels in Chianti Region](https://expedia.ca/Chianti-Region-Hotels.d603148.Travel-Guide-Hotels)[Vacation Rentals in Chianti Region](https://expedia.ca/Chianti-Region-Vacation-Rentals.d603148.Travel-Guide-VacationRentals)[Flights to Chianti Region](https://expedia.ca/Cheap-Flights-To-Chianti-Region.d603148.Travel-Guide-Flights)[Things to do in Chianti Region](https://expedia.ca/Things-To-Do-In-Chianti-Region.d603148.Travel-Guide-Activities)[Chianti Region Car Rentals](https://expedia.ca/Car-Rentals-In-Chianti-Region.d603148.Car-Rental-Guide)[Chianti Region Vacation Packages](https://expedia.ca/Chianti-Region.d603148.Destination-Travel-Guides) ![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/410000/410487-Torre-Del-Mangia.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Winery Hotels in Chianti Region ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Chianti Region Winery Hotels Tonight [Oct 17 - Oct 18](https://www.expedia.ca/Hotel-Search?regionId=603148&startDate=2025-10-17&endDate=2025-10-18&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 18 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=603148&startDate=2025-10-18&endDate=2025-10-19&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=603148&startDate=2025-10-17&endDate=2025-10-19&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=603148&startDate=2025-10-24&endDate=2025-10-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Chianti Region Winery Hotels ![Exterior detail](https://images.trvl-media.com/lodging/10000000/9800000/9797700/9797642/11eaf7f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/10000000/9800000/9797700/9797642/d6216ebc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Double Room](https://images.trvl-media.com/lodging/10000000/9800000/9797700/9797642/84f971b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Banquet hall](https://images.trvl-media.com/lodging/10000000/9800000/9797700/9797642/f4558f63.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### La Certosa di Pontignano Castelnuovo Berardenga 9.6/10 Exceptional (485) "Excellent place to stay even for the next time. " CA $110 CA $128 total includes taxes & fees Oct 23 - Oct 24 [](https://www.expedia.ca/Castelnuovo-Berardenga-Hotels-La-Certosa-Di-Pontignano.h9797642.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/8000000/7570000/7564900/7564854/3167b59e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Junior Suite](https://images.trvl-media.com/lodging/8000000/7570000/7564900/7564854/da2e11e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Villa, 2 Bedrooms | Living area](https://images.trvl-media.com/lodging/8000000/7570000/7564900/7564854/7c35f9bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/8000000/7570000/7564900/7564854/d55388f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Castello Vicchiomaggio Greve in Chianti 9.4/10 Exceptional (368) "Beautiful grounds. Room was spacious and the breakfast was delicious. Very friendly staff." CA $249 CA $274 total includes taxes & fees Oct 18 - Oct 19 [](https://www.expedia.ca/Greve-In-Chianti-Hotels-Castello-Vicchiomaggio.h7564854.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/21000000/20490000/20484000/20483959/56ce48bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/21000000/20490000/20484000/20483959/4eac4992.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/21000000/20490000/20484000/20483959/8e8d0a1b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, premium bedding, minibar, in-room safe](https://images.trvl-media.com/lodging/21000000/20490000/20484000/20483959/7531f1d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Salvadonica - Borgo del Chianti San Casciano in Val di Pesa 9.6/10 Exceptional (250) "Beautiful setting with delicious food and attentive staff " CA $152 CA $174 total includes taxes & fees Nov 12 - Nov 13 [](https://www.expedia.ca/San-Casciano-In-Val-Di-Pesa-Hotels-Salvadonica.h20483959.Hotel-Information) ![2 outdoor pools, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/2000000/1280000/1277600/1277546/1d958423.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 restaurants, breakfast, lunch, dinner served; local cuisine](https://images.trvl-media.com/lodging/2000000/1280000/1277600/1277546/c9ee8535.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Junior Suite | Living area](https://images.trvl-media.com/lodging/2000000/1280000/1277600/1277546/155c6de8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/2000000/1280000/1277600/1277546/133e09c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Borgo Scopeto Wine & Country Relais Castelnuovo Berardenga 9.2/10 Wonderful (188) "This hotel is absolutely gorgeous. The staff, food and grounds are fantastic. Can’t recommend more! Big thanks to Luka and Giuseppe for making our stay so special. Great wine tasting and delicious wine recommendations. Won’t disappoint " CA $424 CA $483 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Castelnuovo-Berardenga-Hotels-Borgo-Scopeto-Relais.h1277546.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/96000000/95120000/95114100/95114066/513e5451.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/96000000/95120000/95114100/95114066/394627d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo | Living area](https://images.trvl-media.com/lodging/96000000/95120000/95114100/95114066/97151d85.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Junior Double Room](https://images.trvl-media.com/lodging/96000000/95120000/95114100/95114066/3c8dbeb0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pieve Aldina - Fontenille Collection Radda in Chianti 10/10 Exceptional (30) "Everything was exquisite!! From the service , the food, wine, olive oil, pool, bedding, room decor, outdoor seating spaces etc etc etc - perfection !!!! We enjoyed celebrating our 25th anniversary here so much and hope we are fortunate enough to come back. " CA $505 CA $569 total includes taxes & fees Nov 1 - Nov 2 [](https://www.expedia.ca/Radda-In-Chianti-Hotels-Pieve-Aldina.h95114066.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/6000000/5590000/5585700/5585638/4a6bd899.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/6000000/5590000/5585700/5585638/27ef3f75.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Villa, Multiple Bedrooms (Il Borro)](https://images.trvl-media.com/lodging/6000000/5590000/5585700/5585638/54b2f9e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Villa, Multiple Bedrooms (Il Borro) | Private kitchen](https://images.trvl-media.com/lodging/6000000/5590000/5585700/5585638/b3606c7e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Il Borro - Relais & Châteaux Loro Ciuffenna 9.2/10 Wonderful (94) "Charming property. Excellent staff and food options. Would recommend booking activities early and try a little of everything. Would also recommend trying each of the three restaurants and a variety of their wines. " CA $626 CA $689 total includes taxes & fees Nov 17 - Nov 18 [](https://www.expedia.ca/Loro-Ciuffenna-Hotels-Il-Borro-Relais-Chateaux.h5585638.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/43000000/42060000/42059900/42059842/aaf98c1b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/43000000/42060000/42059900/42059842/079f0a96.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/43000000/42060000/42059900/42059842/70e53beb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Panoramic Suite, Private Cottage](https://images.trvl-media.com/lodging/43000000/42060000/42059900/42059842/f171cbe1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Torre a Cona Wine Estate Rignano sull'Arno 9.6/10 Exceptional (88) "Beautiful place" CA $417 CA $462 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Rignano-SullArno-Hotels-Torre-A-Cona-Wine-Estate.h42059842.Hotel-Information) ![Outdoor pool, open 9:00 AM to 8:00 PM, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/3000000/2530000/2523800/2523750/d7de1ccd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Courtyard](https://images.trvl-media.com/lodging/3000000/2530000/2523800/2523750/446df379.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Tree House](https://images.trvl-media.com/lodging/3000000/2530000/2523800/2523750/f9e9d290.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Tree House | View from room](https://images.trvl-media.com/lodging/3000000/2530000/2523800/2523750/5794994c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa I Barronci Resort & Spa San Casciano in Val di Pesa 9.2/10 Wonderful (404) "Staff wa really accommodating. Resort really has it all to almost never had to leave they even helped us book a nice wine tour! " CA $133 CA $156 total includes taxes & fees Nov 11 - Nov 12 [](https://www.expedia.ca/San-Casciano-In-Val-Di-Pesa-Hotels-Villa-I-Barronci-Resort-Spa.h2523750.Hotel-Information) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/120000000/119330000/119324400/119324317/a505aa4b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, free WiFi, bed sheets](https://images.trvl-media.com/lodging/120000000/119330000/119324400/119324317/be734942.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/120000000/119330000/119324400/119324317/abc8c9c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Children's area](https://images.trvl-media.com/lodging/120000000/119330000/119324400/119324317/6cf9f8a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Agriturismo Montemagni di Sopra Greve in Chianti 10/10 Exceptional (5) "The hostess is very accommodating and sweet. The beds were incredibly comfy and shower was spacious. A very lovely and peaceful stay! " CA $134 CA $154 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Greve-In-Chianti-Hotels-Agriturismo-Montemagni-Di-Sopra.h119324317.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/27000000/26680000/26676500/26676404/14e5e44b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lunch and dinner served](https://images.trvl-media.com/lodging/27000000/26680000/26676500/26676404/dae3d322.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Suite, Garden View (Master Two Bedroom)](https://images.trvl-media.com/lodging/27000000/26680000/26676500/26676404/db358d9f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lounge](https://images.trvl-media.com/lodging/27000000/26680000/26676500/26676404/a0f4ae0a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Il Verreno Ambra 9.8/10 Exceptional (51) "Absolutely loved our stay! Beautiful property, comfortable beds, and the most kind and attentive staff. Recommend to anyone wanting to stay in the area! " CA $299 CA $329 total includes taxes & fees Oct 18 - Oct 19 [](https://www.expedia.ca/Bucine-Hotels-Il-Verreno.h26676404.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.ca/Hotel-Search?startDate=2025-10-31&endDate=2025-11-01®ionId=603148&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ## Top Chianti Region Hotel Reviews ![Villa I Barronci Resort & Spa](//images.trvl-media.com/lodging/3000000/2530000/2523800/2523750/d7de1ccd_y.jpg) ### Villa I Barronci Resort & Spa 10/10 Excellent "Staff wa really accommodating. Resort really has it all to almost never had to leave they even helped us book a nice wine tour! " [](https://expedia.ca/San-Casciano-In-Val-Di-Pesa-Hotels-Villa-I-Barronci-Resort-Spa.h2523750.Hotel-Information) ![Castello di Fonterutoli Wine Resort](//images.trvl-media.com/lodging/6000000/5180000/5172400/5172395/9f05cf5a_y.jpg) ### Castello di Fonterutoli Wine Resort 10/10 Excellent "It was a glorious place. So quaint, clean and rustic. Very relaxing and peaceful stay. Friendly team members and excellent wine. We met some friendly people on the wine tour. The breakfast was delicious! Many options for those who don’t eat pork and a beautiful location. This is a place to return for another vacation. I will be back! 😊 " [](https://expedia.ca/Castellina-In-Chianti-Hotels-Castello-Di-Fonterutoli.h5172395.Hotel-Information) ![Castello di Spaltenna- Small Luxury Hotels of the World](//images.trvl-media.com/lodging/3000000/2550000/2540800/2540741/75ac6194_y.jpg) ### Castello di Spaltenna- Small Luxury Hotels of the World 10/10 Excellent "Castello di Spaltenna may rank as the best overall lodging experience of my life. Perched on a hill in Chianti, you pass a towering line of Italian Cypress on final approach to the one-time monastery. The Front desk snaps to attention. A warm welcome to introduce us to the gorgeous, quiet property and then we climbed stone steps to room nine. From room nine, we enjoyed a birds eye view of the perfectly manicured lawns, sparking pool, grapevines and olive trees. A feeing of gratitude and tranquility overcame us. We took three dinners and a lunch in the trattoria on site. The Breakfast included in our stay was sprawling, diverse, and healthy choices dotted the offerings. “Capoucino the asked each morning”? Yes! Moto Grazie. The spa has decent offerings and our massages exceeded expectations. We walked down the hill to Gaiole for a simple lunch and beer. In under an hour you can be in Sienna and not much further is San Giminano. Our departure this morning was bittersweet. If you stay here, I hope you feel as we did" [](https://expedia.ca/Gaiole-In-Chianti-Hotels-Castello-Di-Spaltenna.h2540741.Hotel-Information) ![Hotel Villa Campomaggio](//images.trvl-media.com/lodging/4000000/3610000/3605900/3605816/f6f6c579_y.jpg) ### Hotel Villa Campomaggio 10/10 Excellent "Amazing property and amazing staff that made our trip the best part of Italy! Beautiful grounds and such lovely attentiveness, thank you and we hope to be back someday" [](https://expedia.ca/Radda-In-Chianti-Hotels-Hotel-Villa-Campomaggio.h3605816.Hotel-Information) ![Hotel Borgo di Cortefreda Relais](//images.trvl-media.com/lodging/2000000/1220000/1216500/1216478/288cff0c_y.jpg) ### Hotel Borgo di Cortefreda Relais 10/10 Excellent "It’s beautiful, relaxing .. love the cat - please make sure you feed the cat! She’s so sweet! " [](https://expedia.ca/Barberino-Tavarnelle-Hotels-Hotel-Borgo-Di-Cortefreda-Relais.h1216478.Hotel-Information) ![Hotel Toscana Ambassador](//images.trvl-media.com/lodging/2000000/1430000/1429500/1429488/7717f75b_y.jpg) ### Hotel Toscana Ambassador 10/10 Excellent "The staff took great care of us. Found us a late night taxi to take us to and from wedding at wine villa. Served Beers after bar was closed (fyi— the bar was never open). Made up the room even with do not disturb on door. Easy, close parking! " [](https://expedia.ca/Poggibonsi-Hotels-Hotel-Toscana-Ambassador.h1429488.Hotel-Information) ![Il Borro - Relais & Châteaux](//images.trvl-media.com/lodging/6000000/5590000/5585700/5585638/4a6bd899_y.jpg) ### Il Borro - Relais & Châteaux 10/10 Excellent "Charming property. Excellent staff and food options. Would recommend booking activities early and try a little of everything. Would also recommend trying each of the three restaurants and a variety of their wines. " [](https://expedia.ca/Loro-Ciuffenna-Hotels-Il-Borro-Relais-Chateaux.h5585638.Hotel-Information) ![Palazzo Leopoldo Dimora Storica & Spa](//images.trvl-media.com/lodging/1000000/920000/911700/911656/95292913_y.jpg) ### Palazzo Leopoldo Dimora Storica & Spa 10/10 Excellent "Excellent breakfast. " [](https://expedia.ca/Radda-In-Chianti-Hotels-Palazzo-Leopoldo-Dimora-Storica-Spa.h911656.Hotel-Information) ![Villa Sabolini](//images.trvl-media.com/lodging/4000000/3770000/3763200/3763111/72cf22f3_y.jpg) ### Villa Sabolini 10/10 Excellent "Beautiful location and hotel Staff were excellent - thank you" [](https://expedia.ca/Colle-Di-Val-DElsa-Hotels-Villa-Sabolini.h3763111.Hotel-Information) ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Other - More ways to book - [Lgbt Friendly Hotels in Antella](https://www.expedia.ca/Antella-Hotels-LGBT-Friendly-Hotel.0-0-d6142059-tLGBTFriendlyHotel.Travel-Guide-Filter-Hotels) - [Badia Coltibuono Hotels](https://www.expedia.ca/Badia-Coltibuono-Hotels.d553248635975857717.Travel-Guide-Hotels) - [Casole Hotels](https://www.expedia.ca/Casole-Hotels.d3000429476.Travel-Guide-Hotels) - [B&B in Castellina in Chianti](https://www.expedia.ca/Castellina-In-Chianti-Bed-And-Breakfast.d55534-aaBedAndBreakfast.Travel-Guide-Accommodation) - 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