Title: TOP Hotels with Connecting Rooms in Chianti Region for 2025 | 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) ![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/410000/410487-Torre-Del-Mangia.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Search Hotels with Connecting Rooms in Chianti Region ![price find illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__price_find.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 Save instantly and earn perks with One Key [Learn about One Key](https://www.expedia.co.uk/welcome-one-key) ![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 Hotels with Connecting Rooms Tonight [4 Oct - 5 Oct](https://www.expedia.co.uk/Hotel-Search?regionId=603148&startDate=2025-10-04&endDate=2025-10-05&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [5 Oct - 6 Oct](https://www.expedia.co.uk/Hotel-Search?regionId=603148&startDate=2025-10-05&endDate=2025-10-06&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [10 Oct - 12 Oct](https://www.expedia.co.uk/Hotel-Search?regionId=603148&startDate=2025-10-10&endDate=2025-10-12&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [17 Oct - 19 Oct](https://www.expedia.co.uk/Hotel-Search?regionId=603148&startDate=2025-10-17&endDate=2025-10-19&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Chianti Region Hotels with Connecting Rooms ![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) ![Terrace/patio](https://images.trvl-media.com/lodging/11000000/10510000/10507800/10507728/a6497c02.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Double Room | Frette Italian sheets, premium bedding, down duvets, Select Comfort beds](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. " £154 includes taxes & fees 4 Nov - 5 Nov [](https://www.expedia.co.uk/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) ![Lobby sitting area](https://images.trvl-media.com/lodging/6000000/5950000/5948900/5948813/fb0e068f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Double Room | 2 bedrooms, minibar, in-room safe, individually furnished](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 " [](https://www.expedia.co.uk/Florence-Hotels-Villa-Tolomei-Hotel-Resort.h5948813.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/1000000/30000/22600/22579/bc8037ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/30000/22600/22579/8de77b8b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior entrance](https://images.trvl-media.com/lodging/1000000/30000/22600/22579/1b8b315e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool](https://images.trvl-media.com/lodging/1000000/30000/22600/22579/3979fa4f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa Cora Oltrarno 9.8/10 Exceptional (463) "The hotel is very beautiful, and the surrounding environment is also excellent." £459 includes taxes & fees 3 Nov - 4 Nov [](https://www.expedia.co.uk/Florence-Hotels-Villa-Cora.h22579.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) ![Banquet hall](https://images.trvl-media.com/lodging/10000000/9800000/9797700/9797642/f4558f63.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/10000000/9800000/9797700/9797642/d6216ebc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Double Room | Premium bedding, desk, blackout curtains, iron/ironing board](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. " £84 includes taxes & fees 9 Oct - 10 Oct [](https://www.expedia.co.uk/Castelnuovo-Berardenga-Hotels-La-Certosa-Di-Pontignano.h9797642.Hotel-Information) ![2 outdoor pools, pool umbrellas, pool 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 | 55-inch LCD TV with satellite channels, TV](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 " £256 includes taxes & fees 2 Nov - 3 Nov [](https://www.expedia.co.uk/Castelnuovo-Berardenga-Hotels-Borgo-Scopeto-Relais.h1277546.Hotel-Information) ![Seasonal outdoor pool, open 9:00 AM to 7:30 PM, pool umbrellas](https://images.trvl-media.com/lodging/2000000/1500000/1492000/1491964/f2375def.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1500000/1492000/1491964/6322c664.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1500000/1492000/1491964/9acf3969.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1500000/1492000/1491964/f562aa0f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Agriturismo San Sano Gaiole in Chianti 10/10 Exceptional (70) "Great place to stay in Chianti region, quiet and charming property." [](https://www.expedia.co.uk/Gaiole-In-Chianti-Hotels-Hotel-Residence-San-Sano.h1491964.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1620000/1614900/1614881/4e848a61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/2000000/1620000/1614900/1614881/2b5e075e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, Patio (double) | Terrace/patio](https://images.trvl-media.com/lodging/2000000/1620000/1614900/1614881/1d9fee46.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, seasonal outdoor pool, pool loungers](https://images.trvl-media.com/lodging/2000000/1620000/1614900/1614881/7bd8c16b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel Le Fontanelle Castelnuovo Berardenga 9.8/10 Exceptional (94) "We had a perfect stay at this hotel! 100% recommend. " £330 includes taxes & fees 21 Oct - 22 Oct [](https://www.expedia.co.uk/Castelnuovo-Berardenga-Hotels-Hotel-Le-Fontanelle.h1614881.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) ![Exterior](https://images.trvl-media.com/lodging/1000000/800000/797300/797278/36e10829.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 | 32-inch flat-screen TV with satellite channels, TV](https://images.trvl-media.com/lodging/1000000/800000/797300/797278/50c585d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Relais Villa Olmo Impruneta 9.4/10 Exceptional (223) "Wonderful stay- we really enjoyed our stay and did not want to leave!! Beautiful hotel and wonderful service!" £151 includes taxes & fees 3 Nov - 4 Nov [](https://www.expedia.co.uk/Impruneta-Hotels-Relais-Villa-Olmo.h797278.Hotel-Information) ![Family Cottage, 3 Bedrooms (Due Torri) | View from room](https://images.trvl-media.com/lodging/29000000/28630000/28620500/28620497/eca617c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Villa, 5 Bedrooms (Merlo) | Private kitchen | Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/29000000/28630000/28620500/28620497/599f6226.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Rooftop terrace](https://images.trvl-media.com/lodging/29000000/28630000/28620500/28620497/465ac064.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Villa, 6 Bedrooms (Gelso) | Terrace/patio](https://images.trvl-media.com/lodging/29000000/28630000/28620500/28620497/0f0dbf15.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### VIESCA Suites & Villas – Il Borro Toscana Reggello 9.2/10 Wonderful (7) "A dream. Peaceful is the only word that comes to mind. " £225 includes taxes & fees 2 Nov - 3 Nov [](https://www.expedia.co.uk/Reggello-Hotels-VIESCA-Suites-Villas-Il-Borro-Toscana.h28620497.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/3000000/2550000/2542300/2542211/bd706898.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/3000000/2550000/2542300/2542211/9a894adc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 outdoor pools, pool loungers](https://images.trvl-media.com/lodging/3000000/2550000/2542300/2542211/2748a205.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/3000000/2550000/2542300/2542211/6d3bc507.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa Le Barone Greve in Chianti 9.6/10 Exceptional (137) "This was a beautiful property. The staff were very helpful and friendly. I would definitely recommend." £202 includes taxes & fees 31 Oct - 1 Nov [](https://www.expedia.co.uk/Greve-In-Chianti-Hotels-Villa-Le-Barone.h2542211.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=2025-10-18&endDate=2025-10-19®ionId=603148&adults=2&room_amenities_group_explore=connecting_rooms_available&sort=RECOMMENDED&openPlayBack=true) ## Top Chianti Region Hotel Reviews ![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.co.uk/San-Casciano-In-Val-Di-Pesa-Hotels-Villa-I-Barronci-Resort-Spa.h2523750.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.co.uk/Barberino-Tavarnelle-Hotels-Hotel-Borgo-Di-Cortefreda-Relais.h1216478.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.co.uk/Barberino-Tavarnelle-Hotels-COMO-Castello-Del-Nero.h1279768.Hotel-Information) ![Hotel Ristorante Alcide](//images.trvl-media.com/lodging/2000000/1410000/1402100/1402058/d779a567_y.jpg) ### Hotel Ristorante Alcide 8/10 Good "The hotel was good value for the price. The room was clean. The hotel is in a good, safe area. The A/C was able to keep up with the 98F temps outside. Check in was easy. The breakfast was very good. Parking is a little tricky but not to bad. The only issues we had with our room was the safe wouldnt work in one room even after they tried to fix it and there was no safe in our second room and the hot water in the shower would increase and decrease on its own. The beds and pillows were good. We would stay here again!" 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