Title: Book the Best ADVENTURE Hotels in Chianti Region 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 Hotels & Resorts for Couples 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 Hotels & Resorts for Couples Tonight [Oct 16 - Oct 17](https://www.expedia.ca/Hotel-Search?regionId=603148&startDate=2025-10-16&endDate=2025-10-17&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [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) 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 Hotels & Resorts for Couples ![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) ![Garden](https://images.trvl-media.com/lodging/2000000/1140000/1131000/1130942/0dc1dfcd.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" CA $183 CA $202 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Loro-Ciuffenna-Hotels-Villa-Cassia-Di-Baccano.h1130942.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) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/3000000/2530000/2523800/2523750/0e954f88.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) ### Villa I Barronci Resort & Spa San Casciano in Val di Pesa 9.2/10 Wonderful (403) "Beautiful hotel!" 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) ![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) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/900000/891700/891661/59b16350.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 (369) "We had a great stay and loved the 2 bedrooms as a family of 4. Very friendly and accommodating staff" CA $146 CA $164 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Figline-E-Incisa-Valdarno-Hotels-Villa-Casagrande-Resort-SPA.h891661.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) ![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) ![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) ![Buffet](https://images.trvl-media.com/lodging/2000000/1290000/1289200/1289163/0273c2c6.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" CA $145 CA $169 total includes taxes & fees Nov 13 - Nov 14 [](https://www.expedia.ca/Radda-In-Chianti-Hotels-Hotel-Palazzo-San-Niccolo.h1289163.Hotel-Information) ![Deluxe Room | Vineyard view](https://images.trvl-media.com/lodging/1000000/920000/911700/911656/95292913.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, outdoor pool, sun loungers](https://images.trvl-media.com/lodging/1000000/920000/911700/911656/a118885b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Daily buffet breakfast (EUR 13 per person)](https://images.trvl-media.com/lodging/1000000/920000/911700/911656/68b8f035.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Junior Suite (with SPA access)](https://images.trvl-media.com/lodging/1000000/920000/911700/911656/d623efd0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Palazzo Leopoldo Dimora Storica & Spa Radda in Chianti 9.2/10 Wonderful (271) "We loved it was easy to get to wineries or small towns we wanted to visit" CA $213 CA $244 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Radda-In-Chianti-Hotels-Palazzo-Leopoldo-Dimora-Storica-Spa.h911656.Hotel-Information) ![Aerial view](https://images.trvl-media.com/lodging/1000000/800000/797300/797278/c9efa80f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/1000000/800000/797300/797278/b741acfe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Panoramic Suite, Garden View | Living area](https://images.trvl-media.com/lodging/1000000/800000/797300/797278/50c585d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/800000/797300/797278/36e10829.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Relais Villa Olmo Impruneta 9.4/10 Exceptional (226) "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." CA $227 CA $255 total includes taxes & fees Nov 6 - Nov 7 [](https://www.expedia.ca/Impruneta-Hotels-Relais-Villa-Olmo.h797278.Hotel-Information) ![2 outdoor pools](https://images.trvl-media.com/lodging/3000000/2670000/2666600/2666559/b747876b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/3000000/2670000/2666600/2666559/1d1be08a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/3000000/2670000/2666600/2666559/01051ee0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/3000000/2670000/2666600/2666559/0ef6ae05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel Il Pietreto Colle di Val d'Elsa 7.0/10 Good (33) "Beautiful and charming old hotel in the middle of the countryside with a poolside loggia covered in Wisteria and Mock Orange in bloom. We loved it!" CA $149 CA $169 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Colle-Di-Val-DElsa-Hotels-Hotel-Il-Pietreto.h2666559.Hotel-Information) ![Seasonal outdoor pool, open 7 AM to 8:30 PM, pool umbrellas](https://images.trvl-media.com/lodging/2000000/1690000/1685900/1685892/f05836b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Family Room](https://images.trvl-media.com/lodging/2000000/1690000/1685900/1685892/7af01e42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/2000000/1690000/1685900/1685892/7a69a6bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/2000000/1690000/1685900/1685892/ea777c0b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa San Lucchese Poggibonsi 9.4/10 Exceptional (333) "The staff was so kind and helpful. The food and setting of Villa San Lucchese are wonderful." CA $147 CA $172 total includes taxes & fees Oct 17 - Oct 18 [](https://www.expedia.ca/Poggibonsi-Hotels-Villa-San-Lucchese.h1685892.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/1000000/530000/520400/520321/b15846ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/1000000/530000/520400/520321/d19f4d12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dinner served, Italian cuisine, garden views ](https://images.trvl-media.com/lodging/1000000/530000/520400/520321/e96c3801.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior detail](https://images.trvl-media.com/lodging/1000000/530000/520400/520321/afdb83a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Relais Della Rovere Colle di Val d'Elsa 9.0/10 Wonderful (243) "Quietly located hotel with modern rooms and very good dinner option in the courtyard. Spacious pool to relax after long sightseeing days in the countryside." CA $193 CA $215 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Colle-Di-Val-DElsa-Hotels-Relais-Della-Rovere.h520321.Hotel-Information) ![Deluxe Apartment, 1 Bedroom](https://images.trvl-media.com/lodging/7000000/6290000/6285300/6285250/a8721cf6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Suite](https://images.trvl-media.com/lodging/7000000/6290000/6285300/6285250/220d3e8e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/7000000/6290000/6285300/6285250/0b169258.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, Frette Italian sheets, premium bedding, memory foam beds](https://images.trvl-media.com/lodging/7000000/6290000/6285300/6285250/b57d3f0a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Delta Hotel Montevarchi 8.4/10 Very good (158) "Very clean and staff were lovely" CA $160 CA $176 total includes taxes & fees Oct 25 - Oct 26 [](https://www.expedia.ca/Montevarchi-Hotels-Delta-Hotel.h6285250.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=2025-10-30&endDate=2025-10-31®ionId=603148&adults=2&nearby_group=recreation&sort=RECOMMENDED&openPlayBack=true) ## Top Chianti Region Hotel Reviews ![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) ![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 "This magnificent Hotel exceeded all our expectations. The rooms were very generous is size and the beds were so comfy. Breakfast was exceptional too.... The heated swimming pool with Jacuzzi and the view of the countryside was breathtaking." [](https://expedia.ca/San-Casciano-In-Val-Di-Pesa-Hotels-Villa-I-Barronci-Resort-Spa.h2523750.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) ![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 "Amazing experience all around! Stayed for 2 nights!" 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