Title: TOP Hotels with Connecting Rooms 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 Connecting Rooms Tonight [19 Jan - 20 Jan](https://www.expedia.co.uk/Hotel-Search?regionId=603148&startDate=2026-01-19&endDate=2026-01-20&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [20 Jan - 21 Jan](https://www.expedia.co.uk/Hotel-Search?regionId=603148&startDate=2026-01-20&endDate=2026-01-21&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [23 Jan - 25 Jan](https://www.expedia.co.uk/Hotel-Search?regionId=603148&startDate=2026-01-23&endDate=2026-01-25&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [30 Jan - 1 Feb](https://www.expedia.co.uk/Hotel-Search?regionId=603148&startDate=2026-01-30&endDate=2026-02-01&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Chianti Region hotels with connecting rooms ![Exterior](https://images.trvl-media.com/lodging/5000000/4900000/4890100/4890092/f9f34d83.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/5000000/4900000/4890100/4890092/67b6533a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Suite, 2 Bedrooms | View from room](https://images.trvl-media.com/lodging/5000000/4900000/4890100/4890092/74214674.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool, open 9:00 AM to 7:00 PM, pool umbrellas](https://images.trvl-media.com/lodging/5000000/4900000/4890100/4890092/d8b69484.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Torraccia di Chiusi [](https://www.expedia.co.uk/San-Gimignano-Hotels-Torraccia-Di-Chiusi.h4890092.Hotel-Information) San Gimignano 10/10 Exceptional (97 reviews) "A beautiful base for exploring Tuscany away from the crowds." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anthony £159 includes taxes & fees 14 Feb - 15 Feb [](https://www.expedia.co.uk/San-Gimignano-Hotels-Torraccia-Di-Chiusi.h4890092.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/2000000/1220000/1216500/1216478/18221048.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1220000/1216500/1216478/56435536.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, lunch, dinner served; local cuisine, garden views ](https://images.trvl-media.com/lodging/2000000/1220000/1216500/1216478/cf05a6fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Couples treatment room(s), sauna, steam room, Turkish bath/hammam](https://images.trvl-media.com/lodging/2000000/1220000/1216500/1216478/3d30ae6f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel Borgo di Cortefreda Relais [](https://www.expedia.co.uk/Barberino-Tavarnelle-Hotels-Hotel-Borgo-Di-Cortefreda-Relais.h1216478.Hotel-Information) Barberino Tavarnelle 9.4/10 Exceptional (481 reviews) "The views were spectacular and the grounds were so peaceful" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michelle £83 includes taxes & fees 6 Feb - 7 Feb [](https://www.expedia.co.uk/Barberino-Tavarnelle-Hotels-Hotel-Borgo-Di-Cortefreda-Relais.h1216478.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/530000/527600/527532/b7790c0c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/530000/527600/527532/bbf583b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/530000/527600/527532/b0ef245d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool, pool loungers](https://images.trvl-media.com/lodging/1000000/530000/527600/527532/756242b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel Borgo San Luigi [](https://www.expedia.co.uk/Monteriggioni-Hotels-Hotel-Borgo-San-Luigi.h527532.Hotel-Information) Monteriggioni 9.2/10 Wonderful (408 reviews) "Beautiful location with clean rooms and wonderful staff. Really enjoyed the breakfast too! Recommended! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Allyson £104 includes taxes & fees 7 Feb - 8 Feb [](https://www.expedia.co.uk/Monteriggioni-Hotels-Hotel-Borgo-San-Luigi.h527532.Hotel-Information) ![Property entrance](https://images.trvl-media.com/lodging/3000000/2730000/2723600/2723529/4c3be6b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/3000000/2730000/2723600/2723529/c9ef69ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast served, Italian cuisine, al fresco dining ](https://images.trvl-media.com/lodging/3000000/2730000/2723600/2723529/bfbda0d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Memory-foam beds, minibar, individually decorated](https://images.trvl-media.com/lodging/3000000/2730000/2723600/2723529/e7f84930.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa il Fedino [](https://www.expedia.co.uk/San-Casciano-In-Val-Di-Pesa-Hotels-Villa-Il-Fedino.h2723529.Hotel-Information) San Casciano in Val di Pesa 9.6/10 Exceptional (98 reviews) "Great people, great location great service" ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) James £125 includes taxes & fees 5 Feb - 6 Feb [](https://www.expedia.co.uk/San-Casciano-In-Val-Di-Pesa-Hotels-Villa-Il-Fedino.h2723529.Hotel-Information) ![In-room dining](https://images.trvl-media.com/lodging/97000000/96090000/96089000/96088992/4ef3aa51.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/97000000/96090000/96089000/96088992/35053b29.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, down duvets, in-room safe, desk](https://images.trvl-media.com/lodging/97000000/96090000/96089000/96088992/4ad8ff58.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exclusive Studio Suite, 1 Bedroom, Hot Tub, Garden View | Premium bedding, down duvets, in-room safe, desk](https://images.trvl-media.com/lodging/97000000/96090000/96089000/96088992/b9a4ef80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Casa di Palaia [](https://www.expedia.co.uk/Greve-In-Chianti-Hotels-Casa-Di-Palaia.h96088992.Hotel-Information) Greve in Chianti 10/10 Exceptional (22 reviews) "Very well located in the heart if the Tuscany region." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Eli £74 includes taxes & fees 20 Jan - 21 Jan [](https://www.expedia.co.uk/Greve-In-Chianti-Hotels-Casa-Di-Palaia.h96088992.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/3000000/2700000/2690400/2690342/fd869ab3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Aerial view](https://images.trvl-media.com/lodging/3000000/2700000/2690400/2690342/d7d83723.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/3000000/2700000/2690400/2690342/b9b003bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/3000000/2700000/2690400/2690342/01ed134f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### B&B La Fonte del Machiavelli [](https://www.expedia.co.uk/San-Casciano-In-Val-Di-Pesa-Hotels-Bed-And-Breakfast-La-Fonte-Del-Machiavelli.h2690342.Hotel-Information) San Casciano in Val di Pesa 9.2/10 Wonderful (82 reviews) "It was a wonderful stay the bed was comfortable and the view was beautiful. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ruben £97 includes taxes & fees 17 Feb - 18 Feb [](https://www.expedia.co.uk/San-Casciano-In-Val-Di-Pesa-Hotels-Bed-And-Breakfast-La-Fonte-Del-Machiavelli.h2690342.Hotel-Information) ![Outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas](https://images.trvl-media.com/lodging/6000000/5340000/5331800/5331739/59068004.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/6000000/5340000/5331800/5331739/727e0d46.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/6000000/5340000/5331800/5331739/03eeab0b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast meal](https://images.trvl-media.com/lodging/6000000/5340000/5331800/5331739/1d36a1bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Relais Villa Belvedere [](https://www.expedia.co.uk/Figline-E-Incisa-Valdarno-Hotels-Relais-Villa-Belvedere.h5331739.Hotel-Information) Figline e Incisa Valdarno 9.2/10 Wonderful (70 reviews) "Very nice place" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Maria £134 includes taxes & fees 26 Jan - 27 Jan [](https://www.expedia.co.uk/Figline-E-Incisa-Valdarno-Hotels-Relais-Villa-Belvedere.h5331739.Hotel-Information) ![Turkish bath/hammam, body treatments, body scrubs, facials](https://images.trvl-media.com/lodging/1000000/900000/892600/892517/de7e649e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Classic Triple Room, 1 Bedroom, Accessible | Premium bedding, Select Comfort beds, minibar, in-room safe](https://images.trvl-media.com/lodging/1000000/900000/892600/892517/fa624351.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool, pool umbrellas, pool loungers](https://images.trvl-media.com/lodging/1000000/900000/892600/892517/6c9c19d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/1000000/900000/892600/892517/c73e279c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel Il Piccolo Castello [](https://www.expedia.co.uk/Monteriggioni-Hotels-Hotel-Il-Piccolo-Castello.h892517.Hotel-Information) Monteriggioni 8.6/10 Excellent (338 reviews) "We enjoyed our stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joshua £103 includes taxes & fees 20 Jan - 21 Jan [](https://www.expedia.co.uk/Monteriggioni-Hotels-Hotel-Il-Piccolo-Castello.h892517.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) ![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) ![Minibar, in-room safe, desk, blackout curtains](https://images.trvl-media.com/lodging/1000000/70000/66400/66318/d0d4f513.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 (216 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 £108 includes taxes & fees 24 Jan - 25 Jan [](https://www.expedia.co.uk/Montevarchi-Hotels-Hotel-Valdarno.h66318.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/540000/538700/538623/db112677.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Minibar, in-room safe, iron/ironing board, cots/infant beds](https://images.trvl-media.com/lodging/1000000/540000/538700/538623/8e93fcf3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/1000000/540000/538700/538623/4792591a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Check-in/check-out kiosk](https://images.trvl-media.com/lodging/1000000/540000/538700/538623/efc0c3a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel La Vecchia Cartiera [](https://www.expedia.co.uk/Colle-Di-Val-DElsa-Hotels-Hotel-La-Vecchia-Cartiera.h538623.Hotel-Information) Colle di Val d'Elsa 8.4/10 Very good (203 reviews) "The staff was very welcoming. Lovely quiet place. Close to a lot of good restaurants. " ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Sheila £71 includes taxes & fees 20 Jan - 21 Jan [](https://www.expedia.co.uk/Colle-Di-Val-DElsa-Hotels-Hotel-La-Vecchia-Cartiera.h538623.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=2026-02-02&endDate=2026-02-03®ionId=603148&adults=2&room_amenities_group_explore=connecting_rooms_available&sort=RECOMMENDED&openPlayBack=true) ## Top Chianti Region Hotel Reviews ![Hotel Borgo di Cortefreda Relais](https://images.trvl-media.com/lodging/2000000/1220000/1216500/1216478/288cff0c_y.jpg) ### Hotel Borgo di Cortefreda Relais 10/10 Excellent "The hotel and services exceeded my expectations." [](https://expedia.co.uk/Barberino-Tavarnelle-Hotels-Hotel-Borgo-Di-Cortefreda-Relais.h1216478.Hotel-Information) ![COMO Castello Del Nero](https://images.trvl-media.com/lodging/2000000/1280000/1279800/1279768/5908bcb2_y.jpg) ### COMO Castello Del Nero 10/10 Excellent "Wonderful stay. 5-stars across the board if you’re looking for disconnecting and relaxing in the rolling hills of the Tuscan countryside. Easy day/dinner trips to Florence or Siena (rental car). " [](https://expedia.co.uk/Barberino-Tavarnelle-Hotels-COMO-Castello-Del-Nero.h1279768.Hotel-Information) ![Hotel Ristorante Alcide](https://images.trvl-media.com/lodging/2000000/1410000/1402100/1402058/d779a567_y.jpg) ### Hotel Ristorante Alcide 10/10 Excellent "I highly recommended " [](https://expedia.co.uk/Poggibonsi-Hotels-Hotel-Ristorante-Alcide.h1402058.Hotel-Information) ## Explore a world of travel with Expedia - Accommodation - Flights - Packages - Cars - Holiday Homes - Other - [3 Star Hotels in Radda in Chianti ](https://www.expedia.co.uk/3Star-Radda-In-Chianti-Hotels.s30-0-d601693.Travel-Guide-Filter-Hotels) - [Adults Only Resorts & in Castellina in Chianti ](https://www.expedia.co.uk/Castellina-In-Chianti-Hotels-Adults-Only-Resorts.0-0-d55534-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels) - [Beach Resorts & in Castellina in Chianti ](https://www.expedia.co.uk/Castellina-In-Chianti-Hotels-Beach-Hotels.0-0-d55534-tBeachHotels.Travel-Guide-Filter-Hotels) - [Hotels with Restaurant in Castellina in Chianti ](https://www.expedia.co.uk/Castellina-In-Chianti-Hotels-Hotel-With-Restaurant.0-0-d55534-thotelwithrestaurant.Travel-Guide-Filter-Hotels) - 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