Title: Book the Best ROMANTIC Hotels in Chianti Region - 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) ![](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 Romantic Hotels in Chianti Region ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](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) ![bed illustration](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 [Oct 5 - Oct 6](https://www.expedia.ca/Hotel-Search?regionId=603148&startDate=2025-10-05&endDate=2025-10-06&adults=2&travelerType=ROMANTIC&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 6 - Oct 7](https://www.expedia.ca/Hotel-Search?regionId=603148&startDate=2025-10-06&endDate=2025-10-07&adults=2&travelerType=ROMANTIC&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=603148&startDate=2025-10-10&endDate=2025-10-12&adults=2&travelerType=ROMANTIC&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=603148&startDate=2025-10-17&endDate=2025-10-19&adults=2&travelerType=ROMANTIC&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Chianti Region Romantic Hotels ![Exterior detail](https://images.trvl-media.com/lodging/11000000/10510000/10507800/10507728/34e550c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/11000000/10510000/10507800/10507728/23f04f21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Daily buffet breakfast (EUR 20 per person)](https://images.trvl-media.com/lodging/11000000/10510000/10507800/10507728/4bb934b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Double Room](https://images.trvl-media.com/lodging/11000000/10510000/10507800/10507728/6fcc8f08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Art Hotel Villa Agape Oltrarno 9.8/10 Exceptional (1004) "Beautiful hotel, excellent location, extremely nice staff. " CA $242 CA $289 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Florence-Hotels-Art-Hotel-Villa-Agape.h10507728.Hotel-Information) ![Seasonal outdoor pool, open 11:00 AM to 7:00 PM, pool umbrellas](https://images.trvl-media.com/lodging/6000000/5950000/5948900/5948813/10e274a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/6000000/5950000/5948900/5948813/aa3c7fe8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Porch](https://images.trvl-media.com/lodging/6000000/5950000/5948900/5948813/10b5b79e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Double Room](https://images.trvl-media.com/lodging/6000000/5950000/5948900/5948813/2b89c881.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa Tolomei Hotel & Resort Oltrarno 8.8/10 Excellent (394) "Very nice quite resort with a very nice poot and great breakfast " CA $256 CA $308 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Florence-Hotels-Villa-Tolomei-Hotel-Resort.h5948813.Hotel-Information) ![Superior Room, Balcony | Balcony](https://images.trvl-media.com/lodging/1000000/850000/849900/849839/c7d418e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/850000/849900/849839/59e14086.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/1000000/850000/849900/849839/24f89230.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/1000000/850000/849900/849839/056604fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Orto De Medici Hotel Historic Centre of Florence 9.8/10 Exceptional (1000) "Excellent hotel and staff, very good location " CA $231 CA $277 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Florence-Hotels-Orto-De-Medici-Hotel.h849839.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/96000000/95120000/95114100/95114066/513e5451.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Junior Double Room](https://images.trvl-media.com/lodging/96000000/95120000/95114100/95114066/3c8dbeb0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/96000000/95120000/95114100/95114066/394627d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo | Living area](https://images.trvl-media.com/lodging/96000000/95120000/95114100/95114066/97151d85.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pieve Aldina - Fontenille Collection Radda in Chianti 10/10 Exceptional (29) "Everything was exquisite!! From the service , the food, wine, olive oil, pool, bedding, room decor, outdoor seating spaces etc etc etc - perfection !!!! We enjoyed celebrating our 25th anniversary here so much and hope we are fortunate enough to come back. " CA $504 CA $568 total includes taxes & fees Nov 1 - Nov 2 [](https://www.expedia.ca/Radda-In-Chianti-Hotels-Pieve-Aldina.h95114066.Hotel-Information) ![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) ![Body treatments, body scrubs, facials, manicures and pedicures, massages](https://images.trvl-media.com/lodging/1000000/530000/528500/528471/f78cd5e9.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) ![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 (77) "One of our favorite places we’ve ever stayed at. 100% recommend. Hopefully we can visit again. " CA $1,016 CA $1,134 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Castelnuovo-Berardenga-Hotels-Hotel-Borgo-San-Felice.h528471.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/10000000/9800000/9797700/9797642/11eaf7f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/10000000/9800000/9797700/9797642/c3101a79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Banquet hall](https://images.trvl-media.com/lodging/10000000/9800000/9797700/9797642/f4558f63.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Double Room](https://images.trvl-media.com/lodging/10000000/9800000/9797700/9797642/84f971b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### La Certosa di Pontignano Castelnuovo Berardenga 9.6/10 Exceptional (478) "Excellent staff, great food. " CA $138 CA $158 total includes taxes & fees Oct 9 - Oct 10 [](https://www.expedia.ca/Castelnuovo-Berardenga-Hotels-La-Certosa-Di-Pontignano.h9797642.Hotel-Information) ![Indoor pool, outdoor pool, open 8:30 AM to 7 PM, sun loungers](https://images.trvl-media.com/lodging/1000000/870000/862800/862712/64683028.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Aerial view](https://images.trvl-media.com/lodging/1000000/870000/862800/862712/5400ca9b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/870000/862800/862712/8a343c92.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/1000000/870000/862800/862712/f68e355f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa Lecchi Hotel Wellness Poggibonsi 9.4/10 Exceptional (80) "My wife and I spent three nights at this hotel. We enjoyed the facilities- both in the spa and the surrounding areas. The staff are outstanding and take a real pride in ensuring that all our needs are taken care of. Food was excellent and service could not be faulted. Highly recommended." CA $360 CA $406 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Poggibonsi-Hotels-Villa-Lecchi-Hotel-Wellness.h862712.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/8000000/7570000/7564900/7564854/3167b59e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Junior Suite](https://images.trvl-media.com/lodging/8000000/7570000/7564900/7564854/da2e11e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Regional cuisine](https://images.trvl-media.com/lodging/8000000/7570000/7564900/7564854/bf56b5da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/8000000/7570000/7564900/7564854/d55388f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Castello Vicchiomaggio Greve in Chianti 9.4/10 Exceptional (365) "Beautiful grounds. Room was spacious and the breakfast was delicious. Very friendly staff." CA $256 CA $281 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Greve-In-Chianti-Hotels-Castello-Vicchiomaggio.h7564854.Hotel-Information) ![2 outdoor pools, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/2000000/1280000/1277600/1277546/1d958423.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 restaurants, breakfast, lunch, dinner served; local cuisine](https://images.trvl-media.com/lodging/2000000/1280000/1277600/1277546/c9ee8535.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Junior Suite | Living area](https://images.trvl-media.com/lodging/2000000/1280000/1277600/1277546/155c6de8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 restaurants, breakfast, lunch, dinner served; local cuisine](https://images.trvl-media.com/lodging/2000000/1280000/1277600/1277546/e06aa6e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Borgo Scopeto Wine & Country Relais Castelnuovo Berardenga 9.2/10 Wonderful (188) "This hotel is absolutely gorgeous. The staff, food and grounds are fantastic. Can’t recommend more! Big thanks to Luka and Giuseppe for making our stay so special. Great wine tasting and delicious wine recommendations. Won’t disappoint " CA $423 CA $482 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Castelnuovo-Berardenga-Hotels-Borgo-Scopeto-Relais.h1277546.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) ![Interior](https://images.trvl-media.com/lodging/90000000/89240000/89237400/89237342/cbac26e7.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) ### The Club House Castelnuovo Berardenga 10/10 Exceptional (5) "Excellent overall. Amenities. Service. Food. Vibe. All top notch" CA $522 CA $591 total includes taxes & fees Nov 1 - Nov 2 [](https://www.expedia.ca/Castelnuovo-Berardenga-Hotels-The-Club-House.h89237342.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=2025-10-19&endDate=2025-10-20®ionId=603148&adults=2&travelerType=romantic&sort=RECOMMENDED&openPlayBack=true) ## Top Chianti Region Hotel Reviews ![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) ![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 "This hotel is wonderful with beautiful views from the terrace! The only complaint is the number of stairs you have to take if staying on upper floors (no elevator) - my husband has a bad back so that’s a consideration. Also, wish they would accommodate all the guests in the gourmet restaurant as we couldn’t get a reservation during our 2-day stay! Book ahead of time!" [](https://expedia.ca/Gaiole-In-Chianti-Hotels-Castello-Di-Spaltenna.h2540741.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!" [](https://expedia.ca/Castellina-In-Chianti-Hotels-Castello-Di-Fonterutoli.h5172395.Hotel-Information) ![Borgo Vescine](//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) ![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 "Beautiful property at an impressively reasonable price. E-Bike rentals on site were perfect to ride to vineyards nearby. The pool was amazing and the staff. The on site restaurant might have been my best meal in Italy! I would stay again in a heartbeat!" [](https://expedia.ca/Barberino-Tavarnelle-Hotels-Hotel-Borgo-Di-Cortefreda-Relais.h1216478.Hotel-Information) ![Hotel Villa Campomaggio](//images.trvl-media.com/lodging/4000000/3610000/3605900/3605816/f6f6c579_y.jpg) ### Hotel Villa Campomaggio 10/10 Excellent "Quick trip, wonderful stay! The check-in service was 10/10—they even helped us secure a same-night dinner reservation. Dinner was incredible and truly the highlight of our visit!" [](https://expedia.ca/Radda-In-Chianti-Hotels-Hotel-Villa-Campomaggio.h3605816.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 "I am a frequent international traveler and our II Borro experience was among the best. The Concierge staff was amazing! And a key to our great stay. Will recommend without reservation. " [](https://expedia.ca/Loro-Ciuffenna-Hotels-Il-Borro-Relais-Chateaux.h5585638.Hotel-Information) ![COMO Castello Del Nero](//images.trvl-media.com/lodging/2000000/1280000/1279800/1279768/3986de2c_y.jpg) ### COMO Castello Del Nero 10/10 Excellent "Beautiful!" [](https://expedia.ca/Barberino-Tavarnelle-Hotels-COMO-Castello-Del-Nero.h1279768.Hotel-Information) ![Relais Vignale & Spa](//images.trvl-media.com/lodging/2000000/1130000/1122100/1122097/72f1acd5_y.jpg) ### Relais Vignale & Spa 10/10 Excellent "My friend and I had such a relaxing time at Relais!! We both got amazing massages from Natalie, the staff helped me figure out how to get to Rome after, the rooms were GORGEOUS, the pool was spectacular and got great poolside drinks, and the food/wine was the best!!! Stay here for a romantic and relaxing getaway surrounded by Tuscany’s beautiful rolling hills and vineyards. Would definitely come back!" 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