Title: Book the Best Chianti Region Hotels with smoking rooms 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 Smoking Hotels 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 with smoking rooms Tonight [Oct 19 - Oct 20](https://www.expedia.ca/Hotel-Search?regionId=603148&startDate=2025-10-19&endDate=2025-10-20&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 20 - Oct 21](https://www.expedia.ca/Hotel-Search?regionId=603148&startDate=2025-10-20&endDate=2025-10-21&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) In two weeks [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=603148&startDate=2025-10-31&endDate=2025-11-02&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Chianti Region Hotels with smoking rooms ![Exterior](https://images.trvl-media.com/lodging/6000000/5590000/5585700/5585638/4a6bd899.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Villa, Multiple Bedrooms (Il Borro)](https://images.trvl-media.com/lodging/6000000/5590000/5585700/5585638/54b2f9e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/6000000/5590000/5585700/5585638/27ef3f75.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 restaurants, lunch served](https://images.trvl-media.com/lodging/6000000/5590000/5585700/5585638/8d6d7398.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Il Borro - Relais & Châteaux Loro Ciuffenna 9.2/10 Wonderful (95) "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. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lisa CA $629 CA $692 total includes taxes & fees Nov 17 - Nov 18 [](https://www.expedia.ca/Loro-Ciuffenna-Hotels-Il-Borro-Relais-Chateaux.h5585638.Hotel-Information) ![Poolside bar](https://images.trvl-media.com/lodging/2000000/1130000/1122100/1122097/72f1acd5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1130000/1122100/1122097/bd9729ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Land view from property](https://images.trvl-media.com/lodging/2000000/1130000/1122100/1122097/31773bd1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Manor House Balcony Suite | View from room](https://images.trvl-media.com/lodging/2000000/1130000/1122100/1122097/dd8f4786.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Relais Vignale & Spa Radda in Chianti 9.2/10 Wonderful (281) "Beautiful clean quiet. Would visit again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) jaycie CA $232 CA $305 total includes taxes & fees Oct 21 - Oct 22 [](https://www.expedia.ca/Radda-In-Chianti-Hotels-Relais-Vignale-Spa.h1122097.Hotel-Information) ![Lobby lounge](https://images.trvl-media.com/lodging/4000000/3770000/3763200/3763111/72cf22f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/4000000/3770000/3763200/3763111/35b80314.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/4000000/3770000/3763200/3763111/f0b9ee56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/4000000/3770000/3763200/3763111/0cec1f91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa Sabolini Colle di Val d'Elsa 9.2/10 Wonderful (185) "Beautiful location and hotel Staff were excellent - thank you" ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) Amit CA $120 CA $137 total includes taxes & fees Nov 5 - Nov 6 [](https://www.expedia.ca/Colle-Di-Val-DElsa-Hotels-Villa-Sabolini.h3763111.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/78000000/77990000/77981700/77981610/0fa36bf6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior detail](https://images.trvl-media.com/lodging/78000000/77990000/77981700/77981610/f4da56c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Panoramic Studio Suite, 1 King Bed](https://images.trvl-media.com/lodging/78000000/77990000/77981700/77981610/6893387d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/78000000/77990000/77981700/77981610/cbcac354.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Tenuta di Sticciano Certaldo 9.6/10 Exceptional (16) "Excellent all around. Thank you!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) David CA $160 CA $184 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Certaldo-Hotels-Tenuta-Di-Sticciano.h77981610.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 (369) "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 $154 CA $172 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Figline-E-Incisa-Valdarno-Hotels-Villa-Casagrande-Resort-SPA.h891661.Hotel-Information) ![Garden](https://images.trvl-media.com/lodging/2000000/1350000/1348200/1348125/dbdc1d6b.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/2000000/1350000/1348200/1348125/44b2ce32.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Double Room, Garden View | Room amenity](https://images.trvl-media.com/lodging/2000000/1350000/1348200/1348125/d4e76210.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa Castiglione Impruneta 8.6/10 Excellent (250) "Lovely friendly hotel with a gorgeous courtyard for dinner and aperitivo! Great view of Florence? " ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) Jade CA $89 CA $103 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Impruneta-Hotels-Villa-Castiglione.h1348125.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/29000000/28070000/28064500/28064452/3e200148.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/29000000/28070000/28064500/28064452/6a9fa35d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/29000000/28070000/28064500/28064452/2077addd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Villa, 2 Bedrooms, Kitchen, Poolside | Living area](https://images.trvl-media.com/lodging/29000000/28070000/28064500/28064452/a38be1d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Torrebianca Tuscany Rignano sull'Arno 9.6/10 Exceptional (39) "Lovely pool Breakfast good" ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) christine CA $128 CA $145 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Rignano-SullArno-Hotels-Torrebianca-Tuscany.h28064452.Hotel-Information) ![2 restaurants, breakfast served](https://images.trvl-media.com/lodging/90000000/89240000/89237400/89237342/1b4933fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lapina Suite | Terrace/patio](https://images.trvl-media.com/lodging/90000000/89240000/89237400/89237342/06ea4b83.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas](https://images.trvl-media.com/lodging/90000000/89240000/89237400/89237342/7a8f7828.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/90000000/89240000/89237400/89237342/cbac26e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Club House Castelnuovo Berardenga 10/10 Exceptional (5) "Excellent overall. Amenities. Service. Food. Vibe. All top notch" ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Daniel CA $521 CA $589 total includes taxes & fees Nov 1 - Nov 2 [](https://www.expedia.ca/Castelnuovo-Berardenga-Hotels-The-Club-House.h89237342.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/112000000/111990000/111986000/111985970/bdee2f69.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Double or Twin Room](https://images.trvl-media.com/lodging/112000000/111990000/111986000/111985970/899ad316.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/112000000/111990000/111986000/111985970/18ae4543.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Daily buffet breakfast (EUR 13 per person)](https://images.trvl-media.com/lodging/112000000/111990000/111986000/111985970/860e7cbb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Borgo Le Noci Chianti Retreat & Pool Gaiole in Chianti 8.0/10 Very good (2) "We loved our stay here. The views are beautiful and staff is very accommodating. They even opened the restaurant early to accommodate for our young daughter. The restaurant was also amazing! Thank you very much for having us" ![Sweden](https://a.travel-assets.com/egds/marks/flags/se.svg) Sofia CA $151 CA $179 total includes taxes & fees Oct 22 - Oct 23 [](https://www.expedia.ca/Gaiole-In-Chianti-Hotels-Borgo-Le-Noci-Chianti-Retreat-Pool.h111985970.Hotel-Information) ![Seasonal outdoor pool, open 8 AM to 8 PM, sun loungers](https://images.trvl-media.com/lodging/25000000/24070000/24066900/24066836/e6818a0e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Villa, 4 Bedrooms (Villetta) | Living area](https://images.trvl-media.com/lodging/25000000/24070000/24066900/24066836/4feddf40.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Suite, 1 Bedroom, Ground Floor (Legnaia)](https://images.trvl-media.com/lodging/25000000/24070000/24066900/24066836/4a7abec1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Daily buffet breakfast (EUR 25 per person)](https://images.trvl-media.com/lodging/25000000/24070000/24066900/24066836/6fac72e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Borgo Iesolana Bucine 9.0/10 Wonderful (6) "Die Lage und die Weinfarm sind sehr schön gelegen und bilden ein wunderschönes Ensemble. Die Unterkunft war in Ordnung. Bäder könnten sauberer sein. Handtuchwechsel war auch nach drei Tagen nicht. Das Handtuch wurde vom Boden aufgenommen und neu aufgefangen. Frühstück eher spärlich und jeden Tag gleich. Abendessen ganz wunderbar. " ![Germany](https://a.travel-assets.com/egds/marks/flags/de.svg) Picht CA $238 CA $267 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Bucine-Hotels-Borgo-Iesolana.h24066836.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=2025-11-02&endDate=2025-11-03®ionId=603148&adults=2&property_amenities_group_explore=designated_smoking_areas&sort=RECOMMENDED&openPlayBack=true) ## Top Chianti Region Hotel Reviews ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Other - [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) - 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