Title: Book the Best ROMANTIC Hotels in Chianti Region from CA $74 - 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) ![](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__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 [Mar 4 - Mar 5](https://www.expedia.ca/Hotel-Search?regionId=603148&startDate=2026-03-04&endDate=2026-03-05&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) Tomorrow [Mar 5 - Mar 6](https://www.expedia.ca/Hotel-Search?regionId=603148&startDate=2026-03-05&endDate=2026-03-06&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) This weekend [Mar 6 - Mar 8](https://www.expedia.ca/Hotel-Search?regionId=603148&startDate=2026-03-06&endDate=2026-03-08&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) Next weekend [Mar 13 - Mar 15](https://www.expedia.ca/Hotel-Search?regionId=603148&startDate=2026-03-13&endDate=2026-03-15&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) ![Exterior detail](https://images.trvl-media.com/lodging/10000000/9800000/9797700/9797642/46476210.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) ![Terrace/patio](https://images.trvl-media.com/lodging/10000000/9800000/9797700/9797642/d6652f62.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 9.4/10 Exceptional (513 reviews) "Excellent place to stay even for the next time. " ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Xuejie CA $135 CA $155 total includes taxes & fees Mar 19 - Mar 20 [](https://www.expedia.ca/Castelnuovo-Berardenga-Hotels-La-Certosa-Di-Pontignano.h9797642.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1210000/1206900/1206900/c4b7798d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/2000000/1210000/1206900/1206900/a2b58103.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Staircase](https://images.trvl-media.com/lodging/2000000/1210000/1206900/1206900/cd4b8baf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1210000/1206900/1206900/467add1c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Castello di Tornano Wine Resort [](https://www.expedia.ca/Gaiole-In-Chianti-Hotels-Castello-Di-Tornano.h1206900.Hotel-Information) Gaiole in Chianti 9.0/10 Wonderful (100 reviews) "Most beautiful stay with lovely staff" ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Matthew CA $217 CA $251 total includes taxes & fees Mar 23 - Mar 24 [](https://www.expedia.ca/Gaiole-In-Chianti-Hotels-Castello-Di-Tornano.h1206900.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/4000000/3770000/3763200/3763111/0cec1f91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Aerial view](https://images.trvl-media.com/lodging/4000000/3770000/3763200/3763111/141faf36.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/4000000/3770000/3763200/3763111/00571ed7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dinner served, Italian cuisine](https://images.trvl-media.com/lodging/4000000/3770000/3763200/3763111/1f290a11.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa Sabolini [](https://www.expedia.ca/Colle-Di-Val-DElsa-Hotels-Villa-Sabolini.h3763111.Hotel-Information) Colle di Val d'Elsa 9.2/10 Wonderful (189 reviews) "Beautiful location and hotel Staff were excellent - thank you" ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) Amit CA $128 CA $148 total includes taxes & fees Mar 18 - Mar 19 [](https://www.expedia.ca/Colle-Di-Val-DElsa-Hotels-Villa-Sabolini.h3763111.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/8000000/7570000/7564900/7564854/62d09fdf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/8000000/7570000/7564900/7564854/29f2f09e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/8000000/7570000/7564900/7564854/9c42f1e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/8000000/7570000/7564900/7564854/373632fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Castello Vicchiomaggio [](https://www.expedia.ca/Greve-In-Chianti-Hotels-Castello-Vicchiomaggio.h7564854.Hotel-Information) Greve in Chianti 9.4/10 Exceptional (372 reviews) "Very special treat to stay here. We hope to return " ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Cheyenne CA $226 CA $249 total includes taxes & fees Mar 13 - Mar 14 [](https://www.expedia.ca/Greve-In-Chianti-Hotels-Castello-Vicchiomaggio.h7564854.Hotel-Information) ![Daily buffet breakfast (EUR 13 per person)](https://images.trvl-media.com/lodging/1000000/930000/920300/920216/5a39b85d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Double Room](https://images.trvl-media.com/lodging/1000000/930000/920300/920216/a1ca36bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, free cabanas, pool umbrellas](https://images.trvl-media.com/lodging/1000000/930000/920300/920216/fd2ad4e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/930000/920300/920216/b6b29f76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ultimo Mulino Wellness Country Hotel [](https://www.expedia.ca/Gaiole-In-Chianti-Hotels-LUltimo-Mulino.h920216.Hotel-Information) Gaiole in Chianti 8.8/10 Excellent (146 reviews) "Beautiful place all around " ![Australia](https://a.travel-assets.com/egds/marks/flags/au.svg) Rama Toghiani [](https://www.expedia.ca/Gaiole-In-Chianti-Hotels-LUltimo-Mulino.h920216.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/1000000/920000/918700/918681/60fcd28c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/1000000/920000/918700/918681/488f6705.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/920000/918700/918681/23cb164c.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) ### Villa il Poggiale - Dimora Storica [](https://www.expedia.ca/San-Casciano-In-Val-Di-Pesa-Hotels-Villa-Il-Poggiale-Dimora-Storica.h918681.Hotel-Information) San Casciano in Val di Pesa 9.6/10 Exceptional (145 reviews) "Wonderful stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nancy [](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/1000000/530000/528500/528471/d55614eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 restaurants, lunch, dinner served; local cuisine](https://images.trvl-media.com/lodging/1000000/530000/528500/528471/61bcbebb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 restaurants, lunch, dinner served; local cuisine](https://images.trvl-media.com/lodging/1000000/530000/528500/528471/c20d3d3f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool, free cabanas, pool umbrellas](https://images.trvl-media.com/lodging/1000000/530000/528500/528471/b2ecbcf1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Borgo San Felice Resort [](https://www.expedia.ca/Castelnuovo-Berardenga-Hotels-Hotel-Borgo-San-Felice.h528471.Hotel-Information) Castelnuovo Berardenga 9.8/10 Exceptional (79 reviews) "One of our favorite places we’ve ever stayed at. 100% recommend. Hopefully we can visit again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Maria D CA $1,000 CA $1,116 total includes taxes & fees Apr 1 - Apr 2 [](https://www.expedia.ca/Castelnuovo-Berardenga-Hotels-Hotel-Borgo-San-Felice.h528471.Hotel-Information) ![Chapel](https://images.trvl-media.com/lodging/2000000/1120000/1115500/1115409/65906688.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Suite, 1 King Bed | Living area](https://images.trvl-media.com/lodging/2000000/1120000/1115500/1115409/4989b3e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/2000000/1120000/1115500/1115409/3ab5a8f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Suite, 1 King Bed | Terrace/patio](https://images.trvl-media.com/lodging/2000000/1120000/1115500/1115409/3596e44b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Dievole Wine Resort [](https://www.expedia.ca/Castelnuovo-Berardenga-Hotels-Dievole-Wine-Resort.h1115409.Hotel-Information) Castelnuovo Berardenga 9.6/10 Exceptional (180 reviews) "The property was breath taking. Staff was amazing and accommodating. Wonderful experience. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Gimbert CA $419 CA $474 total includes taxes & fees Apr 1 - Apr 2 [](https://www.expedia.ca/Castelnuovo-Berardenga-Hotels-Dievole-Wine-Resort.h1115409.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) ![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) ![Apartment, 1 Bedroom | Garden view](https://images.trvl-media.com/lodging/3000000/2540000/2537900/2537801/eb7fec56.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 (94 reviews) "We had a great time" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anna [](https://www.expedia.ca/Gaiole-In-Chianti-Hotels-Castello-Di-Meleto.h2537801.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) ![Dinner served, Regional cuisine](https://images.trvl-media.com/lodging/2000000/1350000/1348200/1348125/73720f70.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) ![Garden](https://images.trvl-media.com/lodging/2000000/1350000/1348200/1348125/dbdc1d6b.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 (261 reviews) "Nice and cute place. Great price. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jozsef CA $63 CA $74 total includes taxes & fees Mar 8 - Mar 9 [](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=2026-03-18&endDate=2026-03-19®ionId=603148&adults=2&travelerType=romantic&sort=RECOMMENDED&openPlayBack=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.ca/deals?rfrr=AFFINITY_SPRING_PROMO_603148) ## Top Chianti Region Hotel Reviews ![Villa Le Barone](https://images.trvl-media.com/lodging/3000000/2550000/2542300/2542211/2748a205_y.jpg) ### Villa Le Barone 10/10 Excellent "Great experience!!!" [](https://expedia.ca/Greve-In-Chianti-Hotels-Villa-Le-Barone.h2542211.Hotel-Information) ![Castello di Fonterutoli Wine Resort](https://images.trvl-media.com/lodging/6000000/5180000/5172400/5172395/f80bb145_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) ![Borgo Del Cabreo](https://images.trvl-media.com/lodging/18000000/17970000/17963800/17963776/6c72b535_y.jpg) ### Borgo Del Cabreo 10/10 Excellent "This was our second stay here. The service is excellent, staff are so friendly and the room was spotless with a stunning view at breakfast sitting outside. Nice little spread for breakfast. " [](https://expedia.ca/Greve-In-Chianti-Hotels-Borgo-Del-Cabreo.h17963776.Hotel-Information) ![Hotel Borgo di Cortefreda Relais](https://images.trvl-media.com/lodging/2000000/1220000/1216500/1216478/3746921d_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) ![Castello Vicchiomaggio](https://images.trvl-media.com/lodging/8000000/7570000/7564900/7564854/62d09fdf_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.ca/Greve-In-Chianti-Hotels-Castello-Vicchiomaggio.h7564854.Hotel-Information) ![Il Borro - Relais & Châteaux](https://images.trvl-media.com/lodging/6000000/5590000/5585700/5585638/fb1bfe8a_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/3000000/2550000/2540800/2540741/4ff99473_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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