Title: Book the Best ROMANTIC Hotels in Chianti Region from CA $145 - 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 $145 - ![](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 13 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=603148&startDate=2025-12-13&endDate=2025-12-14&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) Tomorrow [Dec 14 - Dec 15](https://www.expedia.ca/Hotel-Search?regionId=603148&startDate=2025-12-14&endDate=2025-12-15&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) Next weekend [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=603148&startDate=2025-12-19&endDate=2025-12-21&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) In two weeks [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=603148&startDate=2025-12-26&endDate=2025-12-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) ## Our top choices for Chianti Region romantic hotels ![Aerial view](https://images.trvl-media.com/lodging/10000000/9800000/9797700/9797642/8a9d9969.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, lunch, dinner served; Italian cuisine, alfresco dining ](https://images.trvl-media.com/lodging/10000000/9800000/9797700/9797642/a55956cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/10000000/9800000/9797700/9797642/74216348.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/10000000/9800000/9797700/9797642/46476210.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### La Certosa di Pontignano [](https://www.expedia.ca/Castelnuovo-Berardenga-Hotels-La-Certosa-Di-Pontignano.h9797642.Hotel-Information) 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 $139 CA $159 total includes taxes & fees Dec 21 - Dec 22 [](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) ![Exterior](https://images.trvl-media.com/lodging/3000000/2540000/2530300/2530284/8affb150.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/3000000/2540000/2530300/2530284/43c6b732.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Borgo di Pietrafitta Relais [](https://www.expedia.ca/Castellina-In-Chianti-Hotels-Borgo-Di-Pietrafitta-Relais.h2530284.Hotel-Information) Castellina in Chianti 9.4/10 Exceptional (169) "Wonderful setting." ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) Simon CA $125 CA $145 total includes taxes & fees Jan 5 - Jan 6, 2026 [](https://www.expedia.ca/Castellina-In-Chianti-Hotels-Borgo-Di-Pietrafitta-Relais.h2530284.Hotel-Information) ![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) ![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) ![Garden](https://images.trvl-media.com/lodging/2000000/1140000/1131000/1130942/0dc1dfcd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa Cassia di Baccano [](https://www.expedia.ca/Loro-Ciuffenna-Hotels-Villa-Cassia-Di-Baccano.h1130942.Hotel-Information) 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 $197 CA $217 total includes taxes & fees Jan 8 - Jan 9, 2026 [](https://www.expedia.ca/Loro-Ciuffenna-Hotels-Villa-Cassia-Di-Baccano.h1130942.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) ![Lunch and dinner served, alfresco dining ](https://images.trvl-media.com/lodging/3000000/2540000/2537900/2537801/afca094e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/3000000/2540000/2537900/2537801/f5b61d12.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 [](https://www.expedia.ca/Gaiole-In-Chianti-Hotels-Castello-Di-Meleto.h2537801.Hotel-Information) Gaiole in Chianti 8.8/10 Excellent (90) "This Castle is AMAZING! Agatha and Victor so kind. I highly recommend this place. Wines are extremely wonderful. We really enjoy the staying." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Karem [](https://www.expedia.ca/Gaiole-In-Chianti-Hotels-Castello-Di-Meleto.h2537801.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/6000000/5180000/5172400/5172395/f80bb145.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, lunch, dinner served; Italian cuisine, garden views ](https://images.trvl-media.com/lodging/6000000/5180000/5172400/5172395/27a5f04f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/6000000/5180000/5172400/5172395/9932f5d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/6000000/5180000/5172400/5172395/70f4f37a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Castello di Fonterutoli Wine Resort [](https://www.expedia.ca/Castellina-In-Chianti-Hotels-Castello-Di-Fonterutoli.h5172395.Hotel-Information) Castellina in Chianti 9.4/10 Exceptional (200) "Clean room, courteous staff, and good winery" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sangchun CA $257 CA $289 total includes taxes & fees Dec 18 - Dec 19 [](https://www.expedia.ca/Castellina-In-Chianti-Hotels-Castello-Di-Fonterutoli.h5172395.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) ![Property grounds](https://images.trvl-media.com/lodging/1000000/900000/891700/891661/af2e1f78.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) ![Couples treatment rooms, sauna, hot tub, steam room, Turkish bath](https://images.trvl-media.com/lodging/1000000/900000/891700/891661/ff372f94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa Casagrande Resort & SPA [](https://www.expedia.ca/Figline-E-Incisa-Valdarno-Hotels-Villa-Casagrande-Resort-SPA.h891661.Hotel-Information) Figline e Incisa Valdarno 9.2/10 Wonderful (374) "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 $141 CA $159 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Figline-E-Incisa-Valdarno-Hotels-Villa-Casagrande-Resort-SPA.h891661.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/3000000/2530000/2524500/2524406/ac1688f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, lunch, dinner served; garden views](https://images.trvl-media.com/lodging/3000000/2530000/2524500/2524406/6f31e4d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Junior Suite](https://images.trvl-media.com/lodging/3000000/2530000/2524500/2524406/f115bff6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, lunch, dinner served; garden views](https://images.trvl-media.com/lodging/3000000/2530000/2524500/2524406/967e2930.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Relais Poggio Borgoni [](https://www.expedia.ca/San-Casciano-In-Val-Di-Pesa-Hotels-Relais-Poggio-Borgoni.h2524406.Hotel-Information) 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 $141 CA $162 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/San-Casciano-In-Val-Di-Pesa-Hotels-Relais-Poggio-Borgoni.h2524406.Hotel-Information) ![Indoor pool, seasonal outdoor pool, sun loungers](https://images.trvl-media.com/lodging/2000000/1290000/1289200/1289163/187ae210.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/2000000/1290000/1289200/1289163/4ad1f017.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) ![Exterior](https://images.trvl-media.com/lodging/2000000/1290000/1289200/1289163/637c56f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel Palazzo San niccolò & Spa [](https://www.expedia.ca/Radda-In-Chianti-Hotels-Hotel-Palazzo-San-Niccolo.h1289163.Hotel-Information) Radda in Chianti 9.2/10 Wonderful (176) "Ideal country setting" ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Dee CA $147 CA $171 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Radda-In-Chianti-Hotels-Hotel-Palazzo-San-Niccolo.h1289163.Hotel-Information) ![Seasonal outdoor pool, open 9:00 AM to 8:00 PM, pool umbrellas](https://images.trvl-media.com/lodging/12000000/11050000/11047100/11047087/58b438dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/12000000/11050000/11047100/11047087/0c523a2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/12000000/11050000/11047100/11047087/e3a4df1b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/12000000/11050000/11047100/11047087/d2ad0eb7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Agriturismo Nerbona [](https://www.expedia.ca/Colle-Di-Val-DElsa-Hotels-Agriturismo-Nerbona.h11047087.Hotel-Information) Colle di Val d'Elsa 9.6/10 Exceptional (18) "Very nice place" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) JULISSA CA $134 CA $150 total includes taxes & fees Dec 18 - Dec 19 [](https://www.expedia.ca/Colle-Di-Val-DElsa-Hotels-Agriturismo-Nerbona.h11047087.Hotel-Information) ![Dinner served, Regional cuisine](https://images.trvl-media.com/lodging/2000000/1350000/1348200/1348125/dcb50280.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/2000000/1350000/1348200/1348125/dbdc1d6b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, open 10:00 AM to 6:00 PM, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/2000000/1350000/1348200/1348125/65b0d93f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Aerial view](https://images.trvl-media.com/lodging/2000000/1350000/1348200/1348125/77e106dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa Castiglione [](https://www.expedia.ca/Impruneta-Hotels-Villa-Castiglione.h1348125.Hotel-Information) Impruneta 8.6/10 Excellent (256) "Nice and cute place. Great price. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jozsef [](https://www.expedia.ca/Impruneta-Hotels-Villa-Castiglione.h1348125.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=2025-12-27&endDate=2025-12-28®ionId=603148&adults=2&travelerType=romantic&sort=RECOMMENDED&openPlayBack=true) ## 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 "Very clean,staff was very kind and helpful. Looking forward to come back! 😊" [](https://expedia.ca/Castellina-In-Chianti-Hotels-Castello-Di-Fonterutoli.h5172395.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.ca/Barberino-Tavarnelle-Hotels-Hotel-Borgo-Di-Cortefreda-Relais.h1216478.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) ![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." [](https://expedia.ca/Impruneta-Hotels-Relais-Villa-Olmo.h797278.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) - [Luxury Hotels in Castellina in Chianti ](https://www.expedia.ca/Castellina-In-Chianti-Hotels-Luxury-Hotel.0-0-d55534-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Hotel Wedding Venues Hotels in Castellina in Chianti ](https://www.expedia.ca/Castellina-In-Chianti-Hotels-Wedding-Hotels.0-0-d55534-tWeddingHotels.Travel-Guide-Filter-Hotels) - 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