Title: Book the Best BOUTIQUE 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 Boutique 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 Boutique Hotels Tonight [Oct 31 - Nov 1](https://www.expedia.ca/Hotel-Search?regionId=603148&startDate=2025-10-31&endDate=2025-11-01&adults=2&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Nov 1 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=603148&startDate=2025-11-01&endDate=2025-11-02&adults=2&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=603148&startDate=2025-10-31&endDate=2025-11-02&adults=2&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=603148&startDate=2025-11-07&endDate=2025-11-09&adults=2&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Chianti Region Boutique Hotels ![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) ![Property grounds](https://images.trvl-media.com/lodging/1000000/530000/528500/528471/ca53ff62.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite Loggia | Garden](https://images.trvl-media.com/lodging/1000000/530000/528500/528471/d88fe9ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool, free cabanas, pool umbrellas](https://images.trvl-media.com/lodging/1000000/530000/528500/528471/739b27a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Borgo San Felice Resort Castelnuovo Berardenga 9.8/10 Exceptional (78) "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 $1,003 CA $1,120 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Castelnuovo-Berardenga-Hotels-Hotel-Borgo-San-Felice.h528471.Hotel-Information) ![Ballroom](https://images.trvl-media.com/lodging/1000000/800000/796700/796662/8b42326b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, Terrace | View from room](https://images.trvl-media.com/lodging/1000000/800000/796700/796662/239d33c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/1000000/800000/796700/796662/102e69cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bars/lounges](https://images.trvl-media.com/lodging/1000000/800000/796700/796662/4fe0a1f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Grand Hotel Continental Siena – Starhotels Collezione Siena City Centre 9.2/10 Wonderful (568) "Very nice hotel " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) mary lou CA $471 CA $528 total includes taxes & fees Nov 28 - Nov 29 [](https://www.expedia.ca/Siena-Hotels-Grand-Hotel-Continental-Siena-Starhotels-Collezione.h796662.Hotel-Information) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/60000/54200/54105/2a00cb08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room](https://images.trvl-media.com/lodging/1000000/60000/54200/54105/270a7649.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Elevator](https://images.trvl-media.com/lodging/1000000/60000/54200/54105/1cd6f0bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room](https://images.trvl-media.com/lodging/1000000/60000/54200/54105/b02f6b83.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel Pendini Historic Centre of Florence 9.6/10 Exceptional (1024) "Perfect location, great breakfasts, hospitable staff" ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Derreck CA $241 CA $285 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Florence-Hotels-Hotel-Pendini.h54105.Hotel-Information) ![Reception](https://images.trvl-media.com/lodging/1000000/20000/14000/13999/84743cc7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/14000/13999/3d12f7de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/1000000/20000/14000/13999/3eacd343.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/14000/13999/6e5f7642.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bernini Palace Historic Centre of Florence 9.6/10 Exceptional (1001) "Beautiful hotel, excellent staff, extremely convenient location" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Liz CA $320 CA $378 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Florence-Hotels-Bernini-Palace.h13999.Hotel-Information) ![Indoor pool, seasonal outdoor pool](https://images.trvl-media.com/lodging/2000000/1860000/1860000/1859917/dfc827da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Soundproofing](https://images.trvl-media.com/lodging/2000000/1860000/1860000/1859917/0d43f7ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1860000/1860000/1859917/81bf5c8c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, seasonal outdoor pool](https://images.trvl-media.com/lodging/2000000/1860000/1860000/1859917/e82d4f58.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Mercure Petriolo Siena Terme Spa Hotel Civitella Paganico 8.8/10 Excellent (232) "We had a great time. I would recommend this hotel when in Tuscany. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mike CA $178 CA $196 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Civitella-Paganico-Hotels-Mercure-Petriolo-Siena-Terme-Spa-Hotel.h1859917.Hotel-Information) ![2 outdoor pools, open 8:30 AM to 6:30 PM, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/3000000/2180000/2173600/2173539/9ace3d4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Villa (Stabbi) | View from room](https://images.trvl-media.com/lodging/3000000/2180000/2173600/2173539/c373f952.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Villa (Sant'Anna)](https://images.trvl-media.com/lodging/3000000/2180000/2173600/2173539/8e24bdea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 restaurants, breakfast, lunch, dinner served; Italian cuisine](https://images.trvl-media.com/lodging/3000000/2180000/2173600/2173539/8826686a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Rosewood Castiglion del Bosco Montalcino 10/10 Exceptional (67) "Definitely the best property in Tuscany.. People, food, amenities, the property itself - all perfect !" ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) IOSEFIN CA $1,679 CA $1,863 total includes taxes & fees Nov 11 - Nov 12 [](https://www.expedia.ca/Montalcino-Hotels-Rosewood-Castiglion-Del-Bosco.h2173539.Hotel-Information) ![Seasonal outdoor pool, open 10:00 AM to 7:00 PM, pool umbrellas](https://images.trvl-media.com/lodging/2000000/1930000/1923100/1923032/f0f5b944.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lounge](https://images.trvl-media.com/lodging/2000000/1930000/1923100/1923032/850497c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1930000/1923100/1923032/f5213917.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room service - dining](https://images.trvl-media.com/lodging/2000000/1930000/1923100/1923032/75da2343.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lupaia Torrita di Siena 10/10 Exceptional (69) "One of the most special stays - from the service to the property - it was perfection! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Madeline CA $917 CA $1,012 total includes taxes & fees Nov 29 - Nov 30 [](https://www.expedia.ca/Torrita-Di-Siena-Hotels-Lupaia.h1923032.Hotel-Information) ![Villa (Thesan) | Terrace/patio](https://images.trvl-media.com/lodging/6000000/5060000/5059000/5058985/4de54dac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite (Castello di Casole)](https://images.trvl-media.com/lodging/6000000/5060000/5059000/5058985/81b4a106.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite (Castello di Casole)](https://images.trvl-media.com/lodging/6000000/5060000/5059000/5058985/08b171fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/6000000/5060000/5059000/5058985/d115d568.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Castello di Casole, A Belmond Hotel, Tuscany Casole d'Elsa 9.6/10 Exceptional (78) "Top-notch hotel. Everything, from the grounds, to the breakfast, to the pool, to the spa + gym, is perfect." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michael CA $1,780 CA $1,961 total includes taxes & fees Nov 7 - Nov 8 [](https://www.expedia.ca/Casole-DElsa-Hotels-Castello-Di-Casole.h5058985.Hotel-Information) ![Lounge](https://images.trvl-media.com/lodging/1000000/10000/6400/6371/849fb031.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, lunch and dinner served](https://images.trvl-media.com/lodging/1000000/10000/6400/6371/67057582.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, lunch and dinner served](https://images.trvl-media.com/lodging/1000000/10000/6400/6371/84ad3fe0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Rooftop terrace](https://images.trvl-media.com/lodging/1000000/10000/6400/6371/aa91965a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Grand Hotel Baglioni Historic Centre of Florence 9.0/10 Wonderful (1047) "Fantastic stay!! A wonderful hotel" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jonathan CA $226 CA $272 total includes taxes & fees Nov 13 - Nov 14 [](https://www.expedia.ca/Florence-Hotels-Grand-Hotel-Baglioni.h6371.Hotel-Information) ![Indoor pool, seasonal outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/910000/904300/904294/00eb5246.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/910000/904300/904294/2574d784.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/1000000/910000/904300/904294/73161e37.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/1000000/910000/904300/904294/4b98a126.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Grotta Giusti Thermal Spa Resort Tuscany, Autograph Collection Monsummano Terme 8.8/10 Excellent (175) "Beautiful place!!!!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lilia CA $291 CA $333 total includes taxes & fees Nov 27 - Nov 28 [](https://www.expedia.ca/Monsummano-Terme-Hotels-Grotta-Giusti-Thermal-Spa-Resort-Tuscany.h904294.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=2025-11-13&endDate=2025-11-14®ionId=603148&adults=2&specialized_stays_group_explore=boutique_property&sort=RECOMMENDED&openPlayBack=true) ## Top Chianti Region Hotel Reviews ![Hotel Certaldo](//images.trvl-media.com/lodging/2000000/1680000/1675500/1675499/0f881b23_y.jpg) ### Hotel Certaldo 10/10 Excellent "Beautiful garden in the back" [](https://expedia.ca/Certaldo-Hotels-Hotel-Certaldo.h1675499.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) - 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