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 ![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 prices for these dates Next weekend [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=603148&startDate=2025-10-10&endDate=2025-10-12&adults=2&lodging=GUEST_HOUSE&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&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=603148&startDate=2025-10-31&endDate=2025-11-02&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=603148&startDate=2025-11-28&endDate=2025-11-30&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Chianti Region Guest Houses ![Garden](https://images.trvl-media.com/lodging/22000000/21500000/21498400/21498347/4700de03.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/22000000/21500000/21498400/21498347/90ece24c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Classic Double Room](https://images.trvl-media.com/lodging/22000000/21500000/21498400/21498347/dc539284.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/22000000/21500000/21498400/21498347/8d7dcacf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ottantotto Firenze Historic Centre of Florence 9.8/10 Exceptional (168) "Fabulous hotel , breakfast was amazing , great location " CA $326 CA $382 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Florence-Hotels-Ottantotto-Firenze.h21498347.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) ![Comfort Double Room](https://images.trvl-media.com/lodging/43000000/42620000/42616700/42616632/b81efe1a.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) ![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) ### Villa Gelsomino Garden Oltrarno 8.8/10 Excellent (126) "Good hotel, a lot of space, nice roof top veranda. Breakfast included " CA $65 CA $95 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Florence-Hotels-Gelsomino-Garden.h42616632.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) ![Superior Suite, 1 King Bed | Living room](https://images.trvl-media.com/lodging/2000000/1120000/1115500/1115409/f6dc2628.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." CA $400 CA $454 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Castelnuovo-Berardenga-Hotels-Dievole-Wine-Resort.h1115409.Hotel-Information) ![Property entrance](https://images.trvl-media.com/lodging/118000000/117410000/117402200/117402183/7a2bcf0b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Triple Room](https://images.trvl-media.com/lodging/118000000/117410000/117402200/117402183/967e8035.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/118000000/117410000/117402200/117402183/ad0d5cd8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Triple Room](https://images.trvl-media.com/lodging/118000000/117410000/117402200/117402183/bc0a9d79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pitti Suite 13 residenza d'epoca Historic Centre of Florence CA $410 CA $470 total includes taxes & fees Nov 1 - Nov 2 [](https://www.expedia.ca/Florence-Hotels-Pitti-Suite-13-Residenza-Depoca.h117402183.Hotel-Information) ![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 $151 CA $173 total includes taxes & fees Oct 5 - Oct 6 [](https://www.expedia.ca/Greve-In-Chianti-Hotels-Casa-Di-Palaia.h96088992.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) ![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) ![Junior Suite | Living area](https://images.trvl-media.com/lodging/2000000/1480000/1470400/1470364/4f7bd788.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) ### Dimora Casa Eugenia Loro Ciuffenna 9.4/10 Exceptional (31) "Nice hotel, beautiful large room. Nice view over the river. " CA $195 CA $215 total includes taxes & fees Oct 7 - Oct 8 [](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) ![Fridge, coffee/tea maker, electric kettle](https://images.trvl-media.com/lodging/17000000/16900000/16896000/16895969/ee78aa57.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" CA $134 CA $152 total includes taxes & fees Oct 12 - Oct 13 [](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) ![Property entrance](https://images.trvl-media.com/lodging/94000000/93500000/93494300/93494210/d8b306e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Room | Bathroom](https://images.trvl-media.com/lodging/94000000/93500000/93494300/93494210/f3a91ac9.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) ### 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. " CA $66 CA $79 total includes taxes & fees Nov 1 - Nov 2 [](https://www.expedia.ca/Barberino-Tavarnelle-Hotels-Homelink-Poggibonsi.h93494210.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) ![Exterior](https://images.trvl-media.com/lodging/34000000/33450000/33449100/33449097/fcc97880.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) ![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) ### Tuscany View, Montalcino Montalcino 8.6/10 Excellent (7) "Very nice place right in town convenient to everything" CA $181 CA $212 total includes taxes & fees Oct 19 - Oct 20 [](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) ![Exterior](https://images.trvl-media.com/lodging/104000000/103040000/103032500/103032408/eb0fe476.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) ![Reception](https://images.trvl-media.com/lodging/104000000/103040000/103032500/103032408/9e8d274c.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 $280 CA $317 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Torrita-Di-Siena-Hotels-Poggio-Paradiso-Resort-Spa.h103032408.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) ![Interior entrance](https://images.trvl-media.com/lodging/3000000/2310000/2306400/2306380/6351228b.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) ![Garden](https://images.trvl-media.com/lodging/3000000/2310000/2306400/2306380/c8ea4e26.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 $124 CA $143 total includes taxes & fees Oct 6 - Oct 7 [](https://www.expedia.ca/Monteriggioni-Hotels-Villa-Montarioso.h2306380.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) ![Shared kitchen](https://images.trvl-media.com/lodging/16000000/15370000/15366400/15366313/43c3729b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/16000000/15370000/15366400/15366313/b1f3746e.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 9.0/10 Wonderful (32) "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." CA $171 CA $194 total includes taxes & fees Oct 12 - Oct 13 [](https://www.expedia.ca/Siena-Hotels-Villa-Sant-Andrea.h15366313.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) ![3-inch Smart TV with digital channels](https://images.trvl-media.com/lodging/106000000/105530000/105521900/105521815/29a9f120.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) ### 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 $255 CA $287 total includes taxes & fees Nov 1 - Nov 2 [](https://www.expedia.ca/Siena-Hotels-Podere-La-Strega.h105521815.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) ![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) ![Interior entrance](https://images.trvl-media.com/lodging/30000000/30000000/29996800/29996795/5bb0f32e.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!" CA $112 CA $149 total includes taxes & fees Oct 30 - Oct 31 [](https://www.expedia.ca/Sovicille-Hotels-LAntico-Borgo-Di-Torri.h29996795.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) ![Room amenity](https://images.trvl-media.com/lodging/30000000/29110000/29107500/29107445/c7730754.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) ![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) ### B&B Le Aquile Siena City Centre 9.8/10 Exceptional (104) "Wonderful location, great hosts and easy walk to the Campo. Would definitely stay again. " CA $147 CA $169 total includes taxes & fees Nov 2 - Nov 3 [](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/70000000/69560000/69557500/69557466/8196efec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room](https://images.trvl-media.com/lodging/70000000/69560000/69557500/69557466/08891111.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) ### 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 $195 CA $221 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Siena-Hotels-Residenza-DEpoca-San-Martino-29.h69557466.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) ![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/6000000/5940000/5933000/5932999/59483e26.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 $113 CA $133 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/San-Gimignano-Hotels-Residenza-DEpoca-Palazzo-Buonaccorsi.h5932999.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) ![Reception](https://images.trvl-media.com/lodging/16000000/15640000/15636900/15636837/b7d5484a.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) ![Exterior](https://images.trvl-media.com/lodging/16000000/15640000/15636900/15636837/7eb33b55.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Relais La Corte Dei Cavalieri Siena City Centre 8.0/10 Very good (72) "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." CA $90 CA $106 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Siena-Hotels-Relais-La-Corte-Dei-Cavalieri.h15636837.Hotel-Information) ![Superior Double or Twin Room](https://images.trvl-media.com/lodging/77000000/76830000/76825300/76825260/a85bd7ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/77000000/76830000/76825300/76825260/26f91a4b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Double or Twin Room | Bathroom](https://images.trvl-media.com/lodging/77000000/76830000/76825300/76825260/4db7b3cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/77000000/76830000/76825300/76825260/65ec60f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### alla scala 1746 Siena City Centre 7.6/10 Good (5) "With access to the beauty of the best of Siena, we absolutely luxuriated and felt the warm vibe of the people, the buildings, the sunshine and the food. It felt magical!" CA $203 CA $230 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Siena-Hotels-Alla-Scala-1746.h76825260.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) | Private kitchen](https://images.trvl-media.com/lodging/45000000/44370000/44362900/44362863/baac5182.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) ### 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." CA $98 CA $114 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/Volterra-Hotels-Il-Sogno-Di-Annalisa.h44362863.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=2025-10-18&endDate=2025-10-19®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 ![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) ![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) ![Hu Norcenni Girasole Village](//images.trvl-media.com/lodging/4000000/3540000/3530100/3530075/dcea3a98_y.jpg) ### Hu Norcenni Girasole Village 10/10 Excellent "Good value for money" [](https://expedia.ca/Figline-E-Incisa-Valdarno-Hotels-Norcenni-Girasole-Village.h3530075.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) ## 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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