Title: Chianti Region Cottages from CA $172 | 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://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__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 In two weeks [Feb 27 - Mar 1](https://www.expedia.ca/Hotel-Search?regionId=603148&startDate=2026-02-27&endDate=2026-03-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Apr 10 - Apr 12](https://www.expedia.ca/Hotel-Search?regionId=603148&startDate=2026-04-10&endDate=2026-04-12&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [May 8 - May 10](https://www.expedia.ca/Hotel-Search?regionId=603148&startDate=2026-05-08&endDate=2026-05-10&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Jun 5 - Jun 7](https://www.expedia.ca/Hotel-Search?regionId=603148&startDate=2026-06-05&endDate=2026-06-07&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Chianti Region cottages ![Exterior](https://images.trvl-media.com/lodging/54000000/53940000/53936600/53936549/db2fa2de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/54000000/53940000/53936600/53936549/24f34cc6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/54000000/53940000/53936600/53936549/125fcc55.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/54000000/53940000/53936600/53936549/5d0123d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### OLIVE TREES HOUSE WITH POOL [](https://www.expedia.ca/Castellina-In-Chianti-Hotels-OLIVE-TREES-HOUSE-WITH-POOL.h53936549.Hotel-Information) Castellina in Chianti [](https://www.expedia.ca/Castellina-In-Chianti-Hotels-OLIVE-TREES-HOUSE-WITH-POOL.h53936549.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/66000000/65560000/65551600/65551595/2e93e61b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/66000000/65560000/65551600/65551595/21a270c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![A heated pool](https://images.trvl-media.com/lodging/66000000/65560000/65551600/65551595/91b08621.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, in-room safe, desk, iron/ironing board](https://images.trvl-media.com/lodging/66000000/65560000/65551600/65551595/a66a18f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Casa La Misura, garden and pool in the heart of Chianti [](https://www.expedia.ca/Castellina-In-Chianti-Hotels-Casa-La-Misura.h65551595.Hotel-Information) Castellina in Chianti 10/10 Exceptional (2 reviews) "What a beautiful stay in the enchanting Tuscan countryside! Every detail was attended to and we could not have felt more at home. We can only dream of returning sometime!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jami B. [](https://www.expedia.ca/Castellina-In-Chianti-Hotels-Casa-La-Misura.h65551595.Hotel-Information) ![Studio, Patio, Ground Floor | Terrace/patio](https://images.trvl-media.com/lodging/3000000/2530000/2524600/2524503/2d60a5ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Studio, Patio, Ground Floor | Private kitchen](https://images.trvl-media.com/lodging/3000000/2530000/2524600/2524503/04effc95.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment, 1 Bedroom, Patio (3 people)](https://images.trvl-media.com/lodging/3000000/2530000/2524600/2524503/dd9dbe0b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/3000000/2530000/2524600/2524503/2fe340cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fullino Nero [](https://www.expedia.ca/Siena-Hotels-Fullino-Nero.h2524503.Hotel-Information) Siena 9.6/10 Exceptional (50 reviews) "Great stay! Clean rooms with air conditioning. Beautiful grounds " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Christian CA $150 CA $172 total includes taxes & fees Feb 15 - Feb 16 [](https://www.expedia.ca/Siena-Hotels-Fullino-Nero.h2524503.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/117000000/116960000/116957400/116957378/1637396e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/117000000/116960000/116957400/116957378/35e78bb3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/117000000/116960000/116957400/116957378/7e336ded.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shower, hair dryer, bidet, towels](https://images.trvl-media.com/lodging/117000000/116960000/116957400/116957378/3c123570.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cosy double room in pretty cottage with WiFi and AC in enchanting Monteaperti [](https://www.expedia.ca/Castelnuovo-Berardenga-Hotels-Cosy-Double-Room-In-Pretty-Cottage-With-WiFi-And-AC-In-Enchanting-Monteaperti.h116957378.Hotel-Information) Monteaperti 10/10 Exceptional (2 reviews) "We loved this place. Modern cabin set in a rustic Tuscan setting. Beautiful property, very comfortable stay, and very attentive staff. Family owned and operated. Amazing restaurant just steps away. A perfect place for respite" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ian F. CA $233 CA $271 total includes taxes & fees Feb 14 - Feb 15 [](https://www.expedia.ca/Castelnuovo-Berardenga-Hotels-Cosy-Double-Room-In-Pretty-Cottage-With-WiFi-And-AC-In-Enchanting-Monteaperti.h116957378.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/117000000/116950000/116946400/116946334/b3dbf14a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/117000000/116950000/116946400/116946334/e1069bf2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/117000000/116950000/116946400/116946334/7737f71a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/117000000/116950000/116946400/116946334/3eab2fb9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming double bedroom in cottage in enchanting Monteaperti with WiFi, AC [](https://www.expedia.ca/Castelnuovo-Berardenga-Hotels-Charming-Double-Bedroom-In-Cottage-In-Enchanting-Monteaperti-With-WiFi.h116946334.Hotel-Information) Monteaperti 10/10 Exceptional (1 review) "This place was fantastic! What a gem. The bed was comfy, the AC was cold, the bathroom was perfect. We shared the cottage with another couple we were traveling with. The bedroom doors open up to a shared living area, the front entrance is through the main indoor dining area.We had breakfast outside each morning. It was perfect. The staff here is just so nice and considerate, a true family affair. A flight of stairs leads down to a lovely restaurant with plentiful outside dining that shouldn't be... ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cary W. CA $233 CA $271 total includes taxes & fees Feb 14 - Feb 15 [](https://www.expedia.ca/Castelnuovo-Berardenga-Hotels-Charming-Double-Bedroom-In-Cottage-In-Enchanting-Monteaperti-With-WiFi.h116946334.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/92000000/91010000/91003000/91002989/a58ca260.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, foosball, table tennis, books](https://images.trvl-media.com/lodging/92000000/91010000/91003000/91002989/f6b00aae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/92000000/91010000/91003000/91002989/0c10f4a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/92000000/91010000/91003000/91002989/dafeb5b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Casa Palmira - Country House [](https://www.expedia.ca/Borgo-San-Lorenzo-Hotels-Casa-Palmira-Country-House.h91002989.Hotel-Information) Firenze CA $1,131 CA $1,297 total includes taxes & fees Feb 18 - Feb 19 [](https://www.expedia.ca/Borgo-San-Lorenzo-Hotels-Casa-Palmira-Country-House.h91002989.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=2026-02-27&endDate=2026-02-28®ionId=603148&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.ca/deals?rfrr=AA_SPRING_PROMO_603148) ## Find vacation rentals that suit your style Villas [](https://www.expedia.ca/Hotel-Search?destination=Chianti+Region%2C+Tuscany%2C+Italy®ionId=603148&latLong=43.534735%2C11.364917&adults=2&startDate=2026-05-14&d1=2026-05-14&endDate=2026-05-17&d2=2026-05-17&lodging=VILLA) Private vacation homes [](https://www.expedia.ca/Hotel-Search?destination=Chianti+Region%2C+Tuscany%2C+Italy®ionId=603148&latLong=43.534735%2C11.364917&adults=2&startDate=2026-05-14&d1=2026-05-14&endDate=2026-05-17&d2=2026-05-17&lodging=VACATION_HOME) Aparthotels [](https://www.expedia.ca/Hotel-Search?destination=Chianti+Region%2C+Tuscany%2C+Italy®ionId=603148&latLong=43.534735%2C11.364917&adults=2&startDate=2026-05-14&d1=2026-05-14&endDate=2026-05-17&d2=2026-05-17&lodging=APART_HOTEL) Residences [](https://www.expedia.ca/Hotel-Search?destination=Chianti+Region%2C+Tuscany%2C+Italy®ionId=603148&latLong=43.534735%2C11.364917&adults=2&startDate=2026-05-14&d1=2026-05-14&endDate=2026-05-17&d2=2026-05-17&lodging=RESIDENCE) Apartments [](https://www.expedia.ca/Hotel-Search?destination=Chianti+Region%2C+Tuscany%2C+Italy®ionId=603148&latLong=43.534735%2C11.364917&adults=2&startDate=2026-05-14&d1=2026-05-14&endDate=2026-05-17&d2=2026-05-17&lodging=APARTMENT) Cabins [](https://www.expedia.ca/Hotel-Search?destination=Chianti+Region%2C+Tuscany%2C+Italy®ionId=603148&latLong=43.534735%2C11.364917&adults=2&startDate=2026-05-14&d1=2026-05-14&endDate=2026-05-17&d2=2026-05-17&lodging=CABIN) Cottages [](https://www.expedia.ca/Hotel-Search?destination=Chianti+Region%2C+Tuscany%2C+Italy®ionId=603148&latLong=43.534735%2C11.364917&adults=2&startDate=2026-05-14&d1=2026-05-14&endDate=2026-05-17&d2=2026-05-17&lodging=COTTAGE) Condos [](https://www.expedia.ca/Hotel-Search?destination=Chianti+Region%2C+Tuscany%2C+Italy®ionId=603148&latLong=43.534735%2C11.364917&adults=2&startDate=2026-05-14&d1=2026-05-14&endDate=2026-05-17&d2=2026-05-17&lodging=CONDO) Chalets [](https://www.expedia.ca/Hotel-Search?destination=Chianti+Region%2C+Tuscany%2C+Italy®ionId=603148&latLong=43.534735%2C11.364917&adults=2&startDate=2026-05-14&d1=2026-05-14&endDate=2026-05-17&d2=2026-05-17&lodging=CHALET) ![](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-Cottages.d603148-aaCottages.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FChianti-Region-Cottages.d603148-aaCottages.Travel-Guide-Accommodation) ## Top Chianti Region Hotel Reviews ![Hotel Palazzo San Lorenzo & SPA](https://images.trvl-media.com/lodging/4000000/3480000/3475000/3474921/1af45070_y.jpg) ### Hotel Palazzo San Lorenzo & SPA 10/10 Excellent "Very good place, clean, good service, great food, the rooms were amazing." [](https://expedia.ca/Colle-Di-Val-DElsa-Hotels-Hotel-Palazzo-San-Lorenzo-SPA.h3474921.Hotel-Information) ![Villa Le Barone](https://images.trvl-media.com/lodging/3000000/2550000/2542300/2542211/bd706898_y.jpg) ### Villa Le Barone 10/10 Excellent "Great experience!!!" [](https://expedia.ca/Greve-In-Chianti-Hotels-Villa-Le-Barone.h2542211.Hotel-Information) ![Villa Casagrande Resort & SPA](https://images.trvl-media.com/lodging/1000000/900000/891700/891661/f41faf16_y.jpg) ### Villa Casagrande Resort & SPA 10/10 Excellent "Always beautiful when I stay here, staff are helpful and every room clean and tidy " [](https://expedia.ca/Figline-E-Incisa-Valdarno-Hotels-Villa-Casagrande-Resort-SPA.h891661.Hotel-Information) ![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.ca/Barberino-Tavarnelle-Hotels-Hotel-Borgo-Di-Cortefreda-Relais.h1216478.Hotel-Information) ![Hotel Toscana Ambassador](https://images.trvl-media.com/lodging/2000000/1430000/1429500/1429488/7717f75b_y.jpg) ### Hotel Toscana Ambassador 10/10 Excellent "We recommend the Toscana Ambassador to everyone, as we had a great experience with its cleanliness, hospitality, friendliness, and an extraordinary breakfast, with excellent service from Ada & Julia and the rest of the crew, from the front desk to room service. If you ever visit Poggibonsi, Tuscany, stay here with no hesitation. " [](https://expedia.ca/Poggibonsi-Hotels-Hotel-Toscana-Ambassador.h1429488.Hotel-Information) ![Salvadonica - Borgo del Chianti](https://images.trvl-media.com/lodging/21000000/20490000/20484000/20483959/56ce48bb_y.jpg) ### Salvadonica - Borgo del Chianti 10/10 Excellent "Great staff, great room and amenities. Outstanding romantic Tuscany location. Going back again." [](https://expedia.ca/San-Casciano-In-Val-Di-Pesa-Hotels-Salvadonica.h20483959.Hotel-Information) ![Agriturismo San Sano](https://images.trvl-media.com/lodging/2000000/1500000/1492000/1491964/f2375def_y.jpg) ### Agriturismo San Sano 10/10 Excellent "You can never go wrong in Toscana , even in off season . San Sano even more so, hidden from mass tourism. " [](https://expedia.ca/Gaiole-In-Chianti-Hotels-Hotel-Residence-San-Sano.h1491964.Hotel-Information) ![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." [](https://expedia.ca/Greve-In-Chianti-Hotels-Castello-Vicchiomaggio.h7564854.Hotel-Information) ![Il Borro - Relais & Châteaux](https://images.trvl-media.com/lodging/6000000/5590000/5585700/5585638/4a6bd899_y.jpg) ### Il Borro - Relais & Châteaux 10/10 Excellent "A one of a kind, unique property amazing cuisine, and the tour we took of the wine cellar was the best I have ever experienced thanks to the helpfulness and knowledge of our guide Sophia" [](https://expedia.ca/Loro-Ciuffenna-Hotels-Il-Borro-Relais-Chateaux.h5585638.Hotel-Information) ## Find out more about Chianti Region ## Chianti Region Cottages information | Number of reviews | 52 | | ----------------- | ----------- | | Accommodation | 29 Cottages | | Lowest Price | CA $172 | | Highest Price | CA $1,297 | ## 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) - 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