Title: Book the Best ROMANTIC Hotels in Chianti Region from CA $119 - Chianti Region Romantic Getaways | 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) ![Chianti Region showing farmland](https://images.trvl-media.com/place/603148/a6b4be95-df3f-44a2-bf6d-bb1e6f500def.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Romantic Hotels in Chianti Region from CA $119 - ![](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 Romantic Hotels Tonight [Dec 1 - Dec 2](https://www.expedia.ca/Hotel-Search?regionId=603148&startDate=2025-12-01&endDate=2025-12-02&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) Tomorrow [Dec 2 - Dec 3](https://www.expedia.ca/Hotel-Search?regionId=603148&startDate=2025-12-02&endDate=2025-12-03&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) This weekend [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=603148&startDate=2025-12-05&endDate=2025-12-07&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) Next weekend [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=603148&startDate=2025-12-12&endDate=2025-12-14&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) ## Top Chianti Region Romantic 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) ![Banquet hall](https://images.trvl-media.com/lodging/10000000/9800000/9797700/9797642/f4558f63.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/10000000/9800000/9797700/9797642/c3101a79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### La Certosa di Pontignano Castelnuovo Berardenga 9.6/10 Exceptional (502) "Excellent place to stay even for the next time. " ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Xuejie CA $105 CA $122 total includes taxes & fees Dec 8 - Dec 9 [](https://www.expedia.ca/Castelnuovo-Berardenga-Hotels-La-Certosa-Di-Pontignano.h9797642.Hotel-Information) ![Restaurant](https://images.trvl-media.com/lodging/3000000/2540000/2530300/2530284/29ec8453.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (Il Torrino) | Private kitchen](https://images.trvl-media.com/lodging/3000000/2540000/2530300/2530284/40bd4847.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment, 2 Bedrooms, Patio (6 Adults) | Living room](https://images.trvl-media.com/lodging/3000000/2540000/2530300/2530284/11fad22b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/3000000/2540000/2530300/2530284/93f882ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Borgo di Pietrafitta Relais Castellina in Chianti 9.4/10 Exceptional (168) "Wonderful setting." ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) Simon CA $150 CA $172 total includes taxes & fees Dec 27 - Dec 28 [](https://www.expedia.ca/Castellina-In-Chianti-Hotels-Borgo-Di-Pietrafitta-Relais.h2530284.Hotel-Information) ![Lobby lounge](https://images.trvl-media.com/lodging/2000000/1140000/1131000/1130942/7a95d976.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Steam room, Turkish bath, body scrubs, massages](https://images.trvl-media.com/lodging/2000000/1140000/1131000/1130942/e763d814.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1140000/1131000/1130942/b50d05a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool, open 9:00 AM to 7:00 PM, sun loungers](https://images.trvl-media.com/lodging/2000000/1140000/1131000/1130942/6055a736.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa Cassia di Baccano Loro Ciuffenna 9.4/10 Exceptional (23) "The staff were great and the villa was amazing" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ralphvincent CA $180 CA $199 total includes taxes & fees Dec 3 - Dec 4 [](https://www.expedia.ca/Loro-Ciuffenna-Hotels-Villa-Cassia-Di-Baccano.h1130942.Hotel-Information) ![2 restaurants, breakfast, lunch, dinner served; Italian cuisine](https://images.trvl-media.com/lodging/1000000/900000/891700/891661/f41faf16.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, seasonal outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/900000/891700/891661/bf339f2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room](https://images.trvl-media.com/lodging/1000000/900000/891700/891661/944ced52.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Couples treatment rooms, sauna, hot tub, steam room, Turkish bath](https://images.trvl-media.com/lodging/1000000/900000/891700/891661/1360d9d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa Casagrande Resort & SPA Figline e Incisa Valdarno 9.2/10 Wonderful (373) "We had a great stay and loved the 2 bedrooms as a family of 4. Very friendly and accommodating staff" ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Stefanie CA $142 CA $159 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Figline-E-Incisa-Valdarno-Hotels-Villa-Casagrande-Resort-SPA.h891661.Hotel-Information) ![Seasonal outdoor pool, sun loungers](https://images.trvl-media.com/lodging/3000000/2540000/2537900/2537801/089cca52.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Tasting room](https://images.trvl-media.com/lodging/3000000/2540000/2537900/2537801/fe1302e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior detail](https://images.trvl-media.com/lodging/3000000/2540000/2537900/2537801/095c274a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Winery](https://images.trvl-media.com/lodging/3000000/2540000/2537900/2537801/cbeec78c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Castello di Meleto Gaiole in Chianti 8.8/10 Excellent (88) "Super clean.. walked in can smell how clean it was. Beautiful location only down side restaurant was close and it was very difficult finding food around on a Monday afternoon. Wine tour is a must had a great time small group but wonderful people.. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michelle [](https://www.expedia.ca/Gaiole-In-Chianti-Hotels-Castello-Di-Meleto.h2537801.Hotel-Information) ![Lunch, dinner served; local cuisine, pool views ](https://images.trvl-media.com/lodging/1000000/920000/918700/918681/a52adc76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/920000/918700/918681/83d82b9d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/920000/918700/918681/977160f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/920000/918700/918681/5afa6482.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa il Poggiale - Dimora Storica San Casciano in Val di Pesa 9.6/10 Exceptional (145) "Wonderful stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nancy CA $106 CA $119 total includes taxes & fees Dec 1 - Dec 2 [](https://www.expedia.ca/San-Casciano-In-Val-Di-Pesa-Hotels-Villa-Il-Poggiale-Dimora-Storica.h918681.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/3000000/2530000/2524500/2524406/c72d4869.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, lunch, dinner served; garden views](https://images.trvl-media.com/lodging/3000000/2530000/2524500/2524406/02c2ebd7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, lunch, dinner served; garden views](https://images.trvl-media.com/lodging/3000000/2530000/2524500/2524406/d6061fdc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Junior Suite](https://images.trvl-media.com/lodging/3000000/2530000/2524500/2524406/079c3c2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Relais Poggio Borgoni San Casciano in Val di Pesa 9.8/10 Exceptional (57) "Very personal, kind & sympathatic Staff. The Place is gorgeous." ![Switzerland](https://a.travel-assets.com/egds/marks/flags/ch.svg) Nils CA $138 CA $159 total includes taxes & fees Dec 2 - Dec 3 [](https://www.expedia.ca/San-Casciano-In-Val-Di-Pesa-Hotels-Relais-Poggio-Borgoni.h2524406.Hotel-Information) ![Borgo Suite with private garden | Terrace/patio](https://images.trvl-media.com/lodging/2000000/1210000/1206900/1206900/ceb71ffc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Aerial view](https://images.trvl-media.com/lodging/2000000/1210000/1206900/1206900/6123c69c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/2000000/1210000/1206900/1206900/0a0d67ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Chapel](https://images.trvl-media.com/lodging/2000000/1210000/1206900/1206900/df15c8c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Castello di Tornano Wine Resort Gaiole in Chianti 9.0/10 Wonderful (100) "Loved our stay here! It was so pretty and the staff was amazing! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jacquelyn [](https://www.expedia.ca/Gaiole-In-Chianti-Hotels-Castello-Di-Tornano.h1206900.Hotel-Information) ![Interior detail](https://images.trvl-media.com/lodging/2000000/1290000/1289200/1289163/b8b0f4e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Buffet](https://images.trvl-media.com/lodging/2000000/1290000/1289200/1289163/0273c2c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Mansarda](https://images.trvl-media.com/lodging/2000000/1290000/1289200/1289163/bb8071f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 restaurants, breakfast served](https://images.trvl-media.com/lodging/2000000/1290000/1289200/1289163/37d88bc1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel Palazzo San niccolò & Spa Radda in Chianti 9.2/10 Wonderful (175) "Ideal country setting" ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Dee CA $286 CA $325 total includes taxes & fees Dec 28 - Dec 29 [](https://www.expedia.ca/Radda-In-Chianti-Hotels-Hotel-Palazzo-San-Niccolo.h1289163.Hotel-Information) ![Breakfast, lunch, dinner served; Italian cuisine, garden views ](https://images.trvl-media.com/lodging/6000000/5180000/5172400/5172395/9f05cf5a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/6000000/5180000/5172400/5172395/d71aded7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Panoramic Suite, Vineyard View | Vineyard view](https://images.trvl-media.com/lodging/6000000/5180000/5172400/5172395/91065266.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Panoramic Suite, Vineyard View](https://images.trvl-media.com/lodging/6000000/5180000/5172400/5172395/e04b84de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Castello di Fonterutoli Wine Resort Castellina in Chianti 9.4/10 Exceptional (198) "Clean room, courteous staff, and good winery" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sangchun CA $257 CA $290 total includes taxes & fees Dec 3 - Dec 4 [](https://www.expedia.ca/Castellina-In-Chianti-Hotels-Castello-Di-Fonterutoli.h5172395.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=2025-12-14&endDate=2025-12-15®ionId=603148&adults=2&travelerType=romantic&sort=RECOMMENDED&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2025/11/05/BEX-BF-25_CA_1_Desktop.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## Black Friday Sale Limited-time deals: save up to 50% on select hotels [Book now](https://expedia.ca/deals?rfrr=AFFINITY_BF_PROMO_603148) ## Top Chianti Region Hotel Reviews ![Castello di Fonterutoli Wine Resort](https://images.trvl-media.com/lodging/6000000/5180000/5172400/5172395/9f05cf5a_y.jpg) ### Castello di Fonterutoli Wine Resort 10/10 Excellent "Amazing experience! The staff were very knowledgeable and helpful in setting up our dinner and wine tour. Room had a beautiful view. This was the best part of our journey through Italy. Keep up the great work! A+ " [](https://expedia.ca/Castellina-In-Chianti-Hotels-Castello-Di-Fonterutoli.h5172395.Hotel-Information) ![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 "Beautiful hotel and spa. Excellent amenities and modern luxuries. " [](https://expedia.ca/Colle-Di-Val-DElsa-Hotels-Hotel-Palazzo-San-Lorenzo-SPA.h3474921.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 staff at the front desk was amazing. When we arrived he greeted us with such a warm smile and welcomed us to the hotel. He absolutely made the hotel experience much better. " [](https://expedia.ca/Barberino-Tavarnelle-Hotels-Hotel-Borgo-Di-Cortefreda-Relais.h1216478.Hotel-Information) ![Villa Castiglione](https://images.trvl-media.com/lodging/2000000/1350000/1348200/1348125/dbdc1d6b_y.jpg) ### Villa Castiglione 10/10 Excellent "Nice and cute place. Great price. " [](https://expedia.ca/Impruneta-Hotels-Villa-Castiglione.h1348125.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.ca/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.ca/Loro-Ciuffenna-Hotels-Il-Borro-Relais-Chateaux.h5585638.Hotel-Information) ![Relais Vignale & Spa](https://images.trvl-media.com/lodging/2000000/1130000/1122100/1122097/72f1acd5_y.jpg) ### Relais Vignale & Spa 10/10 Excellent "great place and great views. breakfast was very good." [](https://expedia.ca/Radda-In-Chianti-Hotels-Relais-Vignale-Spa.h1122097.Hotel-Information) ![Castello di Spaltenna- Small Luxury Hotels of the World](https://images.trvl-media.com/lodging/3000000/2550000/2540800/2540741/75ac6194_y.jpg) ### Castello di Spaltenna- Small Luxury Hotels of the World 10/10 Excellent "The breakfast was fresh with lots of options and a outdoor setting on the property. The property is beautiful, pool area and spa so peaceful. Excellent service in all areas of hotel! " [](https://expedia.ca/Gaiole-In-Chianti-Hotels-Castello-Di-Spaltenna.h2540741.Hotel-Information) ![Relais Villa Olmo](https://images.trvl-media.com/lodging/1000000/800000/797300/797278/c9efa80f_y.jpg) ### Relais Villa Olmo 10/10 Excellent "This is a beautiful Villa with a stunning views. Rooms were large and very clean and the location was wonderful. It was close to Florence and ideal for exploring Tuscany. Restaurant offered delicious buffet breakfast and many other wonderful local dishes for lunch and dinner. I would highly recommend this Villa and would love to stay here again." 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