Title: Chianti Region Guest Houses | 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) ![Chianti Region showing farmland](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/157000/157505-Chianti-Region.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Search Guest Houses 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 prices for these dates Next weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=603148&startDate=2025-10-17&endDate=2025-10-19&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=603148&startDate=2025-10-24&endDate=2025-10-26&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=603148&startDate=2025-11-07&endDate=2025-11-09&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=603148&startDate=2025-12-05&endDate=2025-12-07&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Chianti Region Guest Houses ![Exterior](https://images.trvl-media.com/lodging/97000000/96090000/96089000/96088992/e4040fa1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exclusive Studio Suite, 1 Bedroom, Hot Tub, Garden View](https://images.trvl-media.com/lodging/97000000/96090000/96089000/96088992/b9a4ef80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property entrance](https://images.trvl-media.com/lodging/97000000/96090000/96089000/96088992/aa5161f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Rooftop terrace](https://images.trvl-media.com/lodging/97000000/96090000/96089000/96088992/1b3e0ef4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Casa di Palaia Greve in Chianti 10/10 Exceptional (22) "Very well located in the heart if the Tuscany region." CA $153 CA $175 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Greve-In-Chianti-Hotels-Casa-Di-Palaia.h96088992.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/2000000/1120000/1115500/1115409/3ab5a8f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Suite, 1 Bedroom | Living area](https://images.trvl-media.com/lodging/2000000/1120000/1115500/1115409/c22c91c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 outdoor pools, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/2000000/1120000/1115500/1115409/f93869a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/2000000/1120000/1115500/1115409/966757e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Dievole Wine Resort Castelnuovo Berardenga 9.6/10 Exceptional (173) "This is our third time staying at this property. We absolutely love starting our trip here. Thank you again for your warm hospitality." [](https://www.expedia.ca/Castelnuovo-Berardenga-Hotels-Dievole-Wine-Resort.h1115409.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/2000000/1480000/1470400/1470364/f9a1ff5c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Double or Twin Room](https://images.trvl-media.com/lodging/2000000/1480000/1470400/1470364/e4505d27.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe](https://images.trvl-media.com/lodging/2000000/1480000/1470400/1470364/717186ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/2000000/1480000/1470400/1470364/22ab09d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Dimora Casa Eugenia Loro Ciuffenna 9.4/10 Exceptional (31) "Nice hotel, beautiful large room. Nice view over the river. " CA $196 CA $216 total includes taxes & fees Nov 12 - Nov 13 [](https://www.expedia.ca/Loro-Ciuffenna-Hotels-Dimora-Casa-Eugenia.h1470364.Hotel-Information) ![Outdoor pool, open 8:00 AM to 7:30 PM, sun loungers](https://images.trvl-media.com/lodging/17000000/16900000/16896000/16895969/5da77186.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/17000000/16900000/16896000/16895969/90a4ffb1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Balcony](https://images.trvl-media.com/lodging/17000000/16900000/16896000/16895969/3184e85d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/17000000/16900000/16896000/16895969/5f44afec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Borgo Nuovo San Martino Bucine 6.4/10 (8) "Definitely going back in the summer" [](https://www.expedia.ca/Bucine-Hotels-Borgo-Nuovo-San-Martino.h16895969.Hotel-Information) ![Interior entrance](https://images.trvl-media.com/lodging/94000000/93500000/93494300/93494210/3060142c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exclusive Room](https://images.trvl-media.com/lodging/94000000/93500000/93494300/93494210/07a726a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property entrance](https://images.trvl-media.com/lodging/94000000/93500000/93494300/93494210/d8b306e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/94000000/93500000/93494300/93494210/ccb6570b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Homelink Poggibonsi Barberino Tavarnelle 6.0/10 (11) "We didn't get the e-mail with the codes to the doors. The wifi doesn't connect to the internet. Our room wasn't cleaned during our stay. The place lokks abandoned from the inside. The room wasclean when we arrived. The inside of the place looks nice. " [](https://www.expedia.ca/Barberino-Tavarnelle-Hotels-Homelink-Poggibonsi.h93494210.Hotel-Information) ![Garden](https://images.trvl-media.com/lodging/3000000/2310000/2306400/2306380/4058a4ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/3000000/2310000/2306400/2306380/c8ea4e26.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/3000000/2310000/2306400/2306380/300f35ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Double or Twin Room, Private Bathroom, Garden View](https://images.trvl-media.com/lodging/3000000/2310000/2306400/2306380/d69ccb08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa Montarioso Montarioso 8.6/10 Excellent (132) "Quiet location not far from Siena. Has free parking and free light breakfast. " CA $126 CA $145 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Monteriggioni-Hotels-Villa-Montarioso.h2306380.Hotel-Information) ![Comfort Double Room | Terrace/patio](https://images.trvl-media.com/lodging/43000000/42620000/42616700/42616632/54e10908.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/43000000/42620000/42616700/42616632/52d0a427.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/43000000/42620000/42616700/42616632/4d07cae8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Daily continental breakfast (EUR 8 per person)](https://images.trvl-media.com/lodging/43000000/42620000/42616700/42616632/d407af0d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa Gelsomino Garden Oltrarno 9.0/10 Wonderful (127) "Good hotel, a lot of space, nice roof top veranda. Breakfast included " [](https://www.expedia.ca/Florence-Hotels-Gelsomino-Garden.h42616632.Hotel-Information) ![Courtyard](https://images.trvl-media.com/lodging/6000000/5940000/5933000/5932999/71d708e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/6000000/5940000/5933000/5932999/116c81c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/6000000/5940000/5933000/5932999/e56c169c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![10 bedrooms, Egyptian cotton sheets, premium bedding, down comforters](https://images.trvl-media.com/lodging/6000000/5940000/5933000/5932999/e4ef781a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Residenza d'Epoca Palazzo Buonaccorsi San Gimignano City Centre 8.4/10 Very good (164) "Exceptional building and excellent staff " CA $117 CA $137 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/San-Gimignano-Hotels-Residenza-DEpoca-Palazzo-Buonaccorsi.h5932999.Hotel-Information) ![Classic Double Room | Living area](https://images.trvl-media.com/lodging/34000000/33450000/33449100/33449097/28670b2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Classic Double Room | Living area](https://images.trvl-media.com/lodging/34000000/33450000/33449100/33449097/1f7f6e3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Spa](https://images.trvl-media.com/lodging/34000000/33450000/33449100/33449097/3518c088.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Classic Double Room](https://images.trvl-media.com/lodging/34000000/33450000/33449100/33449097/95389140.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Tuscany View, Montalcino Montalcino 8.6/10 Excellent (8) "Very nice place right in town convenient to everything" CA $180 CA $211 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Montalcino-Hotels-Relais-Donna-Brunella.h33449097.Hotel-Information) ![Lobby sitting area](https://images.trvl-media.com/lodging/104000000/103040000/103032500/103032408/04de6415.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/104000000/103040000/103032500/103032408/e0101054.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/104000000/103040000/103032500/103032408/eb0fe476.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/104000000/103040000/103032500/103032408/158c10e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Poggio Paradiso Resort & Spa Torrita di Siena 10/10 Exceptional (12) "Beautiful resort in a quiet location. Car is essential as it's in a quiet location away from the main tourist towns. Excellent breakfast. Marco made our stay extra special with excellent service and great recommendations for areas to explore nearby. Highly recommended." CA $278 CA $315 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Torrita-Di-Siena-Hotels-Poggio-Paradiso-Resort-Spa.h103032408.Hotel-Information) ![Reception](https://images.trvl-media.com/lodging/16000000/15370000/15366400/15366313/afdd58ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Comfort Double or Twin Room](https://images.trvl-media.com/lodging/16000000/15370000/15366400/15366313/e8c659d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shared kitchen](https://images.trvl-media.com/lodging/16000000/15370000/15366400/15366313/43c3729b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, premium bedding, memory foam beds, minibar](https://images.trvl-media.com/lodging/16000000/15370000/15366400/15366313/36d2b531.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa Sant Andrea Siena 9.2/10 Wonderful (33) "Nice Tuscan Villa, only 10 minutes from city centre, easy parking and moving in and out of the city. The host are great, Cecilia and husband always available to help." [](https://www.expedia.ca/Siena-Hotels-Villa-Sant-Andrea.h15366313.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/30000000/29110000/29107500/29107445/e65b7b8e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Triple Room, Ensuite](https://images.trvl-media.com/lodging/30000000/29110000/29107500/29107445/4f1b1f42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/30000000/29110000/29107500/29107445/ac29b0ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/30000000/29110000/29107500/29107445/3cb8d59c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### B&B Le Aquile Siena City Centre 9.8/10 Exceptional (107) "Wonderful location, great hosts and easy walk to the Campo. Would definitely stay again. " [](https://www.expedia.ca/Siena-Hotels-BB-Le-Aquile.h29107445.Hotel-Information) ![Deluxe Room](https://images.trvl-media.com/lodging/70000000/69560000/69557500/69557466/613f67f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/70000000/69560000/69557500/69557466/2d6ed7e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, in-room safe, individually decorated, desk](https://images.trvl-media.com/lodging/70000000/69560000/69557500/69557466/3a2149fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/70000000/69560000/69557500/69557466/8196efec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Residenza d'Epoca San Martino 29 Siena City Centre 9.8/10 Exceptional (28) "The host was very friendly and helpful. We had a great stay." CA $182 CA $207 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Siena-Hotels-Residenza-DEpoca-San-Martino-29.h69557466.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/106000000/105530000/105521900/105521815/3eca4b57.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/106000000/105530000/105521900/105521815/3209b671.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/106000000/105530000/105521900/105521815/aaf97b3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Elite Studio Suite, 1 Queen Bed, City View, Annex Building | Living area](https://images.trvl-media.com/lodging/106000000/105530000/105521900/105521815/8697acf5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### podere la strega Siena 10/10 Exceptional (4) "Vår vistelse på Podere La Strega var fantastisk! Paret som hade hand om oss var alldeles underbara. Frukosten var trevlig vid ett stort gemensamt bord och god mat, mannen på hotellet ordnade en riktigt bra kaffe! Poolområdet var rent och fräsch och det märktes att de tar väl hand om stället. Vi vill åka tillbaka redan nu!" CA $209 CA $237 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Siena-Hotels-Podere-La-Strega.h105521815.Hotel-Information) ![Double Room (Il Nido)](https://images.trvl-media.com/lodging/45000000/44370000/44362900/44362863/faf06618.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment, 1 Bedroom (In Famiglia) | Living area](https://images.trvl-media.com/lodging/45000000/44370000/44362900/44362863/576e6e12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment, 1 Bedroom (In Famiglia) | Bathroom](https://images.trvl-media.com/lodging/45000000/44370000/44362900/44362863/0d98bb0e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment, 1 Bedroom (In Famiglia) | Living area](https://images.trvl-media.com/lodging/45000000/44370000/44362900/44362863/9a443ea3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Il Sogno di Annalisa Volterra 8.0/10 Very good (15) "Lovely property inside the city walls but away from the high traffic tourist areas. Well equipped with everything you need. Easy check in. We had a lovely visit in Volterra." [](https://www.expedia.ca/Volterra-Hotels-Il-Sogno-Di-Annalisa.h44362863.Hotel-Information) ![Hallway](https://images.trvl-media.com/lodging/104000000/103050000/103044300/103044227/9c0e752b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Romantic Room](https://images.trvl-media.com/lodging/104000000/103050000/103044300/103044227/7fa5faaf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/104000000/103050000/103044300/103044227/58e76e72.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/104000000/103050000/103044300/103044227/b899e74d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Blossoms of Siena Siena City Centre 9.4/10 Exceptional (26) "We really enjoyed our stay!! Everyone was accomodating and we loved Siena." CA $214 CA $242 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Siena-Hotels-Blossoms-Of-Siena.h103044227.Hotel-Information) ![Courtyard](https://images.trvl-media.com/lodging/30000000/30000000/29996800/29996795/db38e523.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Full-size fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/30000000/30000000/29996800/29996795/82b48747.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Double Room (Private external bathroom)](https://images.trvl-media.com/lodging/30000000/30000000/29996800/29996795/bc1bd579.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/30000000/30000000/29996800/29996795/448d5df5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### L'Antico Borgo di Torri Sovicille 8.0/10 Very good (1) "Appartamento confortevole, Lorenzo oste disponibile e molto simpatico. Faceva molto caldo e l'aria condizionata sarebbe gradita. Borgo piccolo ma interessante, ottimo ristorante vicinissimo. Ci torneremo!" [](https://www.expedia.ca/Sovicille-Hotels-LAntico-Borgo-Di-Torri.h29996795.Hotel-Information) ![Minibar, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/16000000/15640000/15636900/15636837/c9a65eed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/16000000/15640000/15636900/15636837/7eb33b55.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/16000000/15640000/15636900/15636837/53a36e08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/16000000/15640000/15636900/15636837/75173796.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Relais La Corte Dei Cavalieri Siena City Centre 8.0/10 Very good (73) "It was a lovely charming apartement with a cozy and comfortable bed. It's a bit cold this time of year but there was a thoughtful little heater and big wool blanket in the room in addition to the radiator which was very warm. Great sleep! Lovely space and everything feels quite walkable here in Siena." [](https://www.expedia.ca/Siena-Hotels-Relais-La-Corte-Dei-Cavalieri.h15636837.Hotel-Information) ![Single Room, 1 Single Bed, Private Bathroom, City View | View from room](https://images.trvl-media.com/lodging/24000000/23070000/23063500/23063422/6b57812f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/24000000/23070000/23063500/23063422/6bac2565.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden view](https://images.trvl-media.com/lodging/24000000/23070000/23063500/23063422/9395e2d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Double Room, Private Bathroom, City View | Bathroom](https://images.trvl-media.com/lodging/24000000/23070000/23063500/23063422/6a93c509.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### B&B San Francesco Cortona Old Town 8.8/10 Excellent (54) "The B&B is charming, the location is perfect, and Beatrice and the staff are so nice!" [](https://www.expedia.ca/Cortona-Hotels-BB-San-Francesco.h23063422.Hotel-Information) ![Breakfast area](https://images.trvl-media.com/lodging/106000000/105540000/105532500/105532486/41f78df1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Frette Italian sheets, premium bedding, down comforters, free minibar](https://images.trvl-media.com/lodging/106000000/105540000/105532500/105532486/d8011075.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/106000000/105540000/105532500/105532486/03854fdf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Frette Italian sheets, premium bedding, down comforters, free minibar](https://images.trvl-media.com/lodging/106000000/105540000/105532500/105532486/bbe7283b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fondaco del Moro Civitella in Val di Chiana 9.6/10 Exceptional (32) "Excellent breakfast, clean, quiet room. " CA $99 CA $108 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/Civitella-In-Val-Di-Chiana-Hotels-Fondaco-Del-Moro.h105532486.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=2025-10-26&endDate=2025-10-27®ionId=603148&adults=2&lodging=GUEST_HOUSE&sort=RECOMMENDED&openPlayBack=true) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FChianti-Region-Guest-Houses.d603148-aaGuestHouses.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FChianti-Region-Guest-Houses.d603148-aaGuestHouses.Travel-Guide-Accommodation) ## Top Chianti Region Hotel Reviews ![Hotel Villa Campomaggio](//images.trvl-media.com/lodging/4000000/3610000/3605900/3605816/f6f6c579_y.jpg) ### Hotel Villa Campomaggio 10/10 Excellent "Amazing property and amazing staff that made our trip the best part of Italy! Beautiful grounds and such lovely attentiveness, thank you and we hope to be back someday" [](https://expedia.ca/Radda-In-Chianti-Hotels-Hotel-Villa-Campomaggio.h3605816.Hotel-Information) ![Hotel Toscana Ambassador](//images.trvl-media.com/lodging/2000000/1430000/1429500/1429488/7717f75b_y.jpg) ### Hotel Toscana Ambassador 10/10 Excellent "The staff took great care of us. Found us a late night taxi to take us to and from wedding at wine villa. Served Beers after bar was closed (fyi— the bar was never open). Made up the room even with do not disturb on door. Easy, close parking! " [](https://expedia.ca/Poggibonsi-Hotels-Hotel-Toscana-Ambassador.h1429488.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 "Charming property. Excellent staff and food options. Would recommend booking activities early and try a little of everything. Would also recommend trying each of the three restaurants and a variety of their wines. " [](https://expedia.ca/Loro-Ciuffenna-Hotels-Il-Borro-Relais-Chateaux.h5585638.Hotel-Information) ![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.ca/San-Casciano-In-Val-Di-Pesa-Hotels-Villa-I-Barronci-Resort-Spa.h2523750.Hotel-Information) ![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) ![Salvadonica - Borgo del Chianti](//images.trvl-media.com/lodging/21000000/20490000/20484000/20483959/56ce48bb_y.jpg) ### Salvadonica - Borgo del Chianti 10/10 Excellent "Very friendly staff. Stunning views! Excellent restaurant on site with breakfast included. Great rooms with plenty of old-world charm. Can't wait to come back!" [](https://expedia.ca/San-Casciano-In-Val-Di-Pesa-Hotels-Salvadonica.h20483959.Hotel-Information) ![Villa Sabolini](//images.trvl-media.com/lodging/4000000/3770000/3763200/3763111/72cf22f3_y.jpg) ### Villa Sabolini 10/10 Excellent "Beautiful location and hotel Staff were excellent - thank you" [](https://expedia.ca/Colle-Di-Val-DElsa-Hotels-Villa-Sabolini.h3763111.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) ## Find out more about Chianti Region ## Chianti Region Guest Houses information | Number of reviews | | | --- | --- | | Accommodation | Guest Houses | | Lowest Price | | | Highest Price | | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Other - More ways to book - [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) - [Luxury Hotels in Castellina in Chianti](https://www.expedia.ca/Castellina-In-Chianti-Hotels-Luxury-Hotel.0-0-d55534-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Hotel Wedding Venues Hotels in Castellina in Chianti](https://www.expedia.ca/Castellina-In-Chianti-Hotels-Wedding-Hotels.0-0-d55534-tWeddingHotels.Travel-Guide-Filter-Hotels) - 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