Title: TOP Hotels with Entertainment in Chianti Region for 2026 | Expedia.co.uk [Chianti Region Travel Guide](https://expedia.co.uk/Chianti-Region.dx603148)[Hotels in Chianti Region](https://expedia.co.uk/Chianti-Region-Hotels.d603148.Travel-Guide-Hotels)[Holiday Rentals in Chianti Region](https://expedia.co.uk/Chianti-Region-Holiday-Rentals.d603148.Travel-Guide-HolidayRentals)[Flights to Chianti Region](https://expedia.co.uk/Cheap-Flights-To-Chianti-Region.d603148.Travel-Guide-Flights)[Things to do in Chianti Region](https://expedia.co.uk/Things-To-Do-In-Chianti-Region.d603148.Travel-Guide-Activities)[Chianti Region Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Chianti-Region.d603148.Car-Hire-Guide)[Chianti Region Holidays](https://expedia.co.uk/Chianti-Region.d603148.Holidays-City-Breaks) ![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__price_find.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Save instantly and earn perks with One Key [Learn about One Key](https://www.expedia.co.uk/welcome-one-key) - ![](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 Entertainment Tonight [8 Feb - 9 Feb](https://www.expedia.co.uk/Hotel-Search?regionId=603148&startDate=2026-02-08&endDate=2026-02-09&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [9 Feb - 10 Feb](https://www.expedia.co.uk/Hotel-Search?regionId=603148&startDate=2026-02-09&endDate=2026-02-10&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [13 Feb - 15 Feb](https://www.expedia.co.uk/Hotel-Search?regionId=603148&startDate=2026-02-13&endDate=2026-02-15&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [20 Feb - 22 Feb](https://www.expedia.co.uk/Hotel-Search?regionId=603148&startDate=2026-02-20&endDate=2026-02-22&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Chianti Region hotels with entertainment ![Regional cuisine](https://images.trvl-media.com/lodging/2000000/1350000/1348200/1348125/dcb50280.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/2000000/1350000/1348200/1348125/dbdc1d6b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, open 10:00 AM to 6:00 PM, pool umbrellas, pool loungers](https://images.trvl-media.com/lodging/2000000/1350000/1348200/1348125/65b0d93f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Aerial view](https://images.trvl-media.com/lodging/2000000/1350000/1348200/1348125/77e106dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa Castiglione [](https://www.expedia.co.uk/Impruneta-Hotels-Villa-Castiglione.h1348125.Hotel-Information) Impruneta 8.6/10 Excellent (259 reviews) "Nice and cute place. Great price. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jozsef £58 includes taxes & fees 10 Feb - 11 Feb [](https://www.expedia.co.uk/Impruneta-Hotels-Villa-Castiglione.h1348125.Hotel-Information) ![Reception](https://images.trvl-media.com/lodging/1000000/70000/66400/66318/6c8143c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Billiards](https://images.trvl-media.com/lodging/1000000/70000/66400/66318/fb06db24.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/1000000/70000/66400/66318/bcd8344b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property entrance](https://images.trvl-media.com/lodging/1000000/70000/66400/66318/f696dcf3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel Valdarno [](https://www.expedia.co.uk/Montevarchi-Hotels-Hotel-Valdarno.h66318.Hotel-Information) Montevarchi 8.8/10 Excellent (217 reviews) "The property was well kept by staff. It was clean and the breakfast every morning was fantastic " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Robert [](https://www.expedia.co.uk/Montevarchi-Hotels-Hotel-Valdarno.h66318.Hotel-Information) ![Outdoor wedding area](https://images.trvl-media.com/lodging/13000000/12070000/12063100/12063027/b01f515e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/13000000/12070000/12063100/12063027/663cd1a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/13000000/12070000/12063100/12063027/37b3c724.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Business centre](https://images.trvl-media.com/lodging/13000000/12070000/12063100/12063027/7ca7ce0c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Castello di Bossi [](https://www.expedia.co.uk/Castelnuovo-Berardenga-Hotels-Casa-Tolomei-Bossi-Di-Sopra.h12063027.Hotel-Information) Castelnuovo Berardenga 7.8/10 Good (8 reviews) "The location is great if you get to the hotel in a car. " ![Mexico](https://a.travel-assets.com/egds/marks/flags/mx.svg) CESAR JAVIER £114 includes taxes & fees 12 Feb - 13 Feb [](https://www.expedia.co.uk/Castelnuovo-Berardenga-Hotels-Casa-Tolomei-Bossi-Di-Sopra.h12063027.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/79000000/78170000/78165700/78165677/9fd29a0d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/79000000/78170000/78165700/78165677/1e6c21a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, ping pong](https://images.trvl-media.com/lodging/79000000/78170000/78165700/78165677/fb904e73.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, ping pong](https://images.trvl-media.com/lodging/79000000/78170000/78165700/78165677/c326d5ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa Milani with Shared Pool, Private Terrace & Wi-Fi [](https://www.expedia.co.uk/Montespertoli-Hotels-Villa-Milani-With-Shared-Pool.h78165677.Hotel-Information) Montespertoli 10/10 Exceptional (1 review) "The Villa was charming and absolutely bursting with character. We loved exploring the house and the grounds! It was quiet and relaxing, but still only a short drive from Florence, Sienna, San Gimignano and other favorite towns of Tuscany. A memorable stay in an absolutely unique villa!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Scott M. £1,392 includes taxes & fees 10 Feb - 11 Feb [](https://www.expedia.co.uk/Montespertoli-Hotels-Villa-Milani-With-Shared-Pool.h78165677.Hotel-Information) ![Dinner served, al fresco dining ](https://images.trvl-media.com/lodging/2000000/1610000/1604300/1604285/d1c916cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Double Room, Garden View | View from room](https://images.trvl-media.com/lodging/2000000/1610000/1604300/1604285/f6136b74.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Executive Suite (Jacuzzi) | Down duvets, memory-foam beds, minibar, in-room safe](https://images.trvl-media.com/lodging/2000000/1610000/1604300/1604285/9b3b942d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hallway](https://images.trvl-media.com/lodging/2000000/1610000/1604300/1604285/66e21d21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel La Scaletta Al Ponte Vecchio [](https://www.expedia.co.uk/Florence-Hotels-Hotel-La-Scaletta-Florence.h1604285.Hotel-Information) Historic Centre of Florence 8.8/10 Excellent (959 reviews) "Very quiet, huge room. Very comfortable bed. In a perfect location, staff is very friendly. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Amanda £86 includes taxes & fees 9 Feb - 10 Feb [](https://www.expedia.co.uk/Florence-Hotels-Hotel-La-Scaletta-Florence.h1604285.Hotel-Information) ![Daily English breakfast (EUR 15 per person)](https://images.trvl-media.com/lodging/2000000/1690000/1682800/1682730/23cbe536.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Minibar, in-room safe, desk, blackout curtains](https://images.trvl-media.com/lodging/2000000/1690000/1682800/1682730/241b25ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Courtyard](https://images.trvl-media.com/lodging/2000000/1690000/1682800/1682730/39dc475e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium Double Room | Minibar, in-room safe, desk, blackout curtains](https://images.trvl-media.com/lodging/2000000/1690000/1682800/1682730/dc0bd8f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel Silla [](https://www.expedia.co.uk/Florence-Hotels-Hotel-Silla.h1682730.Hotel-Information) Historic Centre of Florence 9.0/10 Wonderful (786 reviews) "The room was very spacious and clean. The breakfast was really good and was always getting refilled. Overall, I had a great experience in the hotel. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Vivian £79 includes taxes & fees 26 Feb - 27 Feb [](https://www.expedia.co.uk/Florence-Hotels-Hotel-Silla.h1682730.Hotel-Information) ![Breakfast buffet](https://images.trvl-media.com/lodging/1000000/920000/913600/913526/w5461h3637x5y0-ad6a6137.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/920000/913600/913526/6fd8ef9f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/920000/913600/913526/d9d2a48e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/920000/913600/913526/5aee1d22.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Globus Urban Hotel [](https://www.expedia.co.uk/Florence-Hotels-Globus-Urban-Hotel.h913526.Hotel-Information) Historic Centre of Florence 9.4/10 Exceptional (1,072 reviews) "Great location" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Yeni £107 includes taxes & fees 26 Feb - 27 Feb [](https://www.expedia.co.uk/Florence-Hotels-Globus-Urban-Hotel.h913526.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/1000000/530000/528500/528470/edea64a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/1000000/530000/528500/528470/4c3dd1ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/530000/528500/528470/0990c118.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast ](https://images.trvl-media.com/lodging/1000000/530000/528500/528470/6ea94788.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel Certosa Di Maggiano [](https://www.expedia.co.uk/Siena-Hotels-Hotel-Certosa-Di-Maggiano.h528470.Hotel-Information) Siena 9.8/10 Exceptional (186 reviews) "The best in Siena." ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) David £176 includes taxes & fees 3 Mar - 4 Mar [](https://www.expedia.co.uk/Siena-Hotels-Hotel-Certosa-Di-Maggiano.h528470.Hotel-Information) ![Bar (on property)](https://images.trvl-media.com/lodging/2000000/1320000/1315000/1314959/6c69e565.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Comfort Double Room | Minibar, in-room safe, desk, laptop workspace](https://images.trvl-media.com/lodging/2000000/1320000/1315000/1314959/304a196c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/2000000/1320000/1315000/1314959/68f1fcbc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Double Room, City View | View from room](https://images.trvl-media.com/lodging/2000000/1320000/1315000/1314959/fd249de8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel Leon Bianco [](https://www.expedia.co.uk/San-Gimignano-Hotels-Hotel-Leon-Bianco.h1314959.Hotel-Information) San Gimignano City Centre 9.4/10 Exceptional (574 reviews) "Great breakfast, clean room, great staff, and great value overall" ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Brandon £90 includes taxes & fees 4 Mar - 5 Mar [](https://www.expedia.co.uk/San-Gimignano-Hotels-Hotel-Leon-Bianco.h1314959.Hotel-Information) ![Daily buffet breakfast (EUR 16 per person)](https://images.trvl-media.com/lodging/3000000/2530000/2529900/2529872/f424471e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property entrance](https://images.trvl-media.com/lodging/3000000/2530000/2529900/2529872/4f86f506.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Double Room | Down duvets, in-room safe, desk, laptop workspace](https://images.trvl-media.com/lodging/3000000/2530000/2529900/2529872/703b73bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Double Room, 1 Queen Bed | Down duvets, in-room safe, desk, laptop workspace](https://images.trvl-media.com/lodging/3000000/2530000/2529900/2529872/2379ff14.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Florence Old Bridge [](https://www.expedia.co.uk/Florence-Hotels-Florence-Old-Bridge.h2529872.Hotel-Information) Historic Centre of Florence 8.2/10 Very good (365 reviews) "Loved our stay.. wonderful location " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jeff £68 includes taxes & fees 9 Feb - 10 Feb [](https://www.expedia.co.uk/Florence-Hotels-Florence-Old-Bridge.h2529872.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.co.uk/Hotel-Search?startDate=2026-02-22&endDate=2026-02-23®ionId=603148&adults=2&nearby_group=entertainment&sort=RECOMMENDED&openPlayBack=true) ## Top Chianti Region Hotel Reviews ![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." 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