Title: Book the Best ROMANTIC Hotels in Chianti Region from CA $114 - 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 [Jan 31 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=603148&startDate=2026-01-31&endDate=2026-02-01&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) Tomorrow [Feb 1 - Feb 2](https://www.expedia.ca/Hotel-Search?regionId=603148&startDate=2026-02-01&endDate=2026-02-02&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) Next weekend [Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=603148&startDate=2026-02-06&endDate=2026-02-08&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) In two weeks [Feb 13 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=603148&startDate=2026-02-13&endDate=2026-02-15&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/2000000/1220000/1216500/1216478/54415207.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool, open 9:00 AM to 7:30 PM, pool umbrellas](https://images.trvl-media.com/lodging/2000000/1220000/1216500/1216478/331cb229.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1220000/1216500/1216478/56435536.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast area](https://images.trvl-media.com/lodging/2000000/1220000/1216500/1216478/9bff591b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel Borgo di Cortefreda Relais [](https://www.expedia.ca/Barberino-Tavarnelle-Hotels-Hotel-Borgo-Di-Cortefreda-Relais.h1216478.Hotel-Information) Barberino Tavarnelle 9.4/10 Exceptional (483 reviews) "The views were spectacular and the grounds were so peaceful" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michelle CA $132 CA $155 total includes taxes & fees Mar 3 - Mar 4 [](https://www.expedia.ca/Barberino-Tavarnelle-Hotels-Hotel-Borgo-Di-Cortefreda-Relais.h1216478.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) ![Meeting facility](https://images.trvl-media.com/lodging/6000000/5180000/5172400/5172395/9932f5d5.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) ![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 (201 reviews) "Amazing experience all around! Stayed for 2 nights!" ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Matthew CA $263 CA $295 total includes taxes & fees Feb 27 - Feb 28 [](https://www.expedia.ca/Castellina-In-Chianti-Hotels-Castello-Di-Fonterutoli.h5172395.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) ![Winery](https://images.trvl-media.com/lodging/3000000/2540000/2537900/2537801/cbeec78c.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) ### Castello di Meleto [](https://www.expedia.ca/Gaiole-In-Chianti-Hotels-Castello-Di-Meleto.h2537801.Hotel-Information) Gaiole in Chianti 8.8/10 Excellent (93 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) ![Exterior](https://images.trvl-media.com/lodging/5000000/4900000/4890100/4890092/f9f34d83.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/5000000/4900000/4890100/4890092/ff2e2ae0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Suite, 2 Bedrooms | View from room](https://images.trvl-media.com/lodging/5000000/4900000/4890100/4890092/74214674.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/5000000/4900000/4890100/4890092/67b6533a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Torraccia di Chiusi [](https://www.expedia.ca/San-Gimignano-Hotels-Torraccia-Di-Chiusi.h4890092.Hotel-Information) San Gimignano 10/10 Exceptional (97 reviews) "A beautiful base for exploring Tuscany away from the crowds." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anthony CA $256 CA $290 total includes taxes & fees Feb 17 - Feb 18 [](https://www.expedia.ca/San-Gimignano-Hotels-Torraccia-Di-Chiusi.h4890092.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/530000/527600/527532/b7790c0c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/530000/527600/527532/bbf583b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/1000000/530000/527600/527532/1214b9be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/530000/527600/527532/b0ef245d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel Borgo San Luigi [](https://www.expedia.ca/Monteriggioni-Hotels-Hotel-Borgo-San-Luigi.h527532.Hotel-Information) Monteriggioni 9.2/10 Wonderful (408 reviews) "Beautiful location with clean rooms and wonderful staff. Really enjoyed the breakfast too! Recommended! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Allyson [](https://www.expedia.ca/Monteriggioni-Hotels-Hotel-Borgo-San-Luigi.h527532.Hotel-Information) ![View from property](https://images.trvl-media.com/lodging/3000000/2530000/2523800/2523750/57a598f5.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) ![Terrace/patio](https://images.trvl-media.com/lodging/3000000/2530000/2523800/2523750/542b0aa1.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/3000000/2530000/2523800/2523750/c9252ea1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa I Barronci Resort & Spa [](https://www.expedia.ca/San-Casciano-In-Val-Di-Pesa-Hotels-Villa-I-Barronci-Resort-Spa.h2523750.Hotel-Information) San Casciano in Val di Pesa 9.2/10 Wonderful (411 reviews) "Staff wa really accommodating. Resort really has it all to almost never had to leave they even helped us book a nice wine tour! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Luis CA $95 CA $114 total includes taxes & fees Feb 1 - Feb 2 [](https://www.expedia.ca/San-Casciano-In-Val-Di-Pesa-Hotels-Villa-I-Barronci-Resort-Spa.h2523750.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) ![Garden](https://images.trvl-media.com/lodging/2000000/1140000/1131000/1130942/0dc1dfcd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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) ### 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 reviews) "The staff were great and the villa was amazing" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ralphvincent CA $219 CA $241 total includes taxes & fees Feb 2 - Feb 3 [](https://www.expedia.ca/Loro-Ciuffenna-Hotels-Villa-Cassia-Di-Baccano.h1130942.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) ![Front of property](https://images.trvl-media.com/lodging/3000000/2530000/2524500/2524406/c0076df5.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 (58 reviews) "Staff was really helpful and the place was charming" ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Samuel CA $142 CA $163 total includes taxes & fees Feb 26 - Feb 27 [](https://www.expedia.ca/San-Casciano-In-Val-Di-Pesa-Hotels-Relais-Poggio-Borgoni.h2524406.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) ![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 detail](https://images.trvl-media.com/lodging/12000000/11050000/11047100/11047087/0c523a2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/12000000/11050000/11047100/11047087/f80e256a.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 reviews) "Very nice place" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) JULISSA CA $131 CA $147 total includes taxes & fees Feb 21 - Feb 22 [](https://www.expedia.ca/Colle-Di-Val-DElsa-Hotels-Agriturismo-Nerbona.h11047087.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) ![Lobby sitting area](https://images.trvl-media.com/lodging/2000000/1290000/1289200/1289163/7c981965.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) ### 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 (180 reviews) "Ideal country setting" ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Dee CA $142 CA $166 total includes taxes & fees Feb 5 - Feb 6 [](https://www.expedia.ca/Radda-In-Chianti-Hotels-Hotel-Palazzo-San-Niccolo.h1289163.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=2026-02-14&endDate=2026-02-15®ionId=603148&adults=2&travelerType=romantic&sort=RECOMMENDED&openPlayBack=true) ## 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 "Livia was amazing and made me feel very welcomed. She has great customer service skills and showed me where places were on the map. The room and bathroom was spacious." [](https://expedia.ca/Colle-Di-Val-DElsa-Hotels-Hotel-Palazzo-San-Lorenzo-SPA.h3474921.Hotel-Information) ![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) ![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.ca/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.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) ![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) ![Borgo Vescine](https://images.trvl-media.com/lodging/2000000/1190000/1180600/1180553/8d2f3252_y.jpg) ### Borgo Vescine 10/10 Excellent "This was a beautiful location. The room was spacious and loved the patio for coffee in the mornings. It was very private. We enjoyed the pool and restaurants were great. Breakfast was amazing. We did the picnic and dinner in the Olive Garden and loved getting to know others at our table. The chefs food choices were so wonderful. We would definitely stay again. " [](https://expedia.ca/Radda-In-Chianti-Hotels-Il-Borgo-Di-Vescine.h1180553.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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