Title: Book the Best Castellina in Chianti WINERY Hotels in 2026 | Expedia.ca

[Castellina in Chianti Travel Guide](https://expedia.ca/Castellina-In-Chianti.dx55534)[Hotels in Castellina in Chianti](https://expedia.ca/Castellina-In-Chianti-Hotels.d55534.Travel-Guide-Hotels)[Vacation Rentals in Castellina in Chianti](https://expedia.ca/Castellina-In-Chianti-Vacation-Rentals.d55534.Travel-Guide-VacationRentals)[Flights to Castellina in Chianti](https://expedia.ca/Cheap-Flights-To-Castellina-In-Chianti.d55534.Travel-Guide-Flights)[Castellina in Chianti Car Rentals](https://expedia.ca/Car-Rentals-In-Castellina-In-Chianti.d55534.Car-Rental-Guide)[Castellina in Chianti Vacation Packages](https://expedia.ca/Castellina-In-Chianti.d55534.Destination-Travel-Guides)

![Castellina in Chianti showing heritage architecture, religious elements and a church or cathedral](https://images.trvl-media.com/place/55534/68deebc9-9310-492d-8f83-85d906ba54aa.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

# Find Winery Hotels in Castellina in Chianti from CA $145

- ![](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 availability on Castellina in Chianti Winery Hotels

Tonight

[Dec 14 - Dec 15](https://www.expedia.ca/Hotel-Search?regionId=55534&startDate=2025-12-14&endDate=2025-12-15&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Dec 15 - Dec 16](https://www.expedia.ca/Hotel-Search?regionId=55534&startDate=2025-12-15&endDate=2025-12-16&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=55534&startDate=2025-12-19&endDate=2025-12-21&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two weeks

[Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=55534&startDate=2025-12-26&endDate=2025-12-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Castellina in Chianti hotels with winery

![Restaurant](https://images.trvl-media.com/lodging/3000000/2540000/2530300/2530284/29ec8453.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/3000000/2540000/2530300/2530284/93f882ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment, 2 Bedrooms, Patio (6 Adults) | Living room](https://images.trvl-media.com/lodging/3000000/2540000/2530300/2530284/11fad22b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (Il Torrino) | Private kitchen](https://images.trvl-media.com/lodging/3000000/2540000/2530300/2530284/40bd4847.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Borgo di Pietrafitta Relais

[](https://www.expedia.ca/Castellina-In-Chianti-Hotels-Borgo-Di-Pietrafitta-Relais.h2530284.Hotel-Information)

Castellina in Chianti

9.4/10

Exceptional

(169)

"Wonderful setting."

![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg)

Simon

CA $125

CA $145 total

includes taxes & fees

Jan 5 - Jan 6, 2026

[](https://www.expedia.ca/Castellina-In-Chianti-Hotels-Borgo-Di-Pietrafitta-Relais.h2530284.Hotel-Information)

![Outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/3000000/2550000/2540800/2540748/5edc5b37.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/3000000/2550000/2540800/2540748/37ac4429.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/3000000/2550000/2540800/2540748/4cc4dd78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lounge](https://images.trvl-media.com/lodging/3000000/2550000/2540800/2540748/8fc9f594.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hotel Colle Etrusco Salivolpi

[](https://www.expedia.ca/Castellina-In-Chianti-Hotels-Hotel-Colle-Etrusco-Salivolpi.h2540748.Hotel-Information)

Castellina in Chianti

9.6/10

Exceptional

(114)

"Friendly staff and walking distance to town"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Scott

CA $196

CA $221 total

includes taxes & fees

Jan 2 - Jan 3, 2026

[](https://www.expedia.ca/Castellina-In-Chianti-Hotels-Hotel-Colle-Etrusco-Salivolpi.h2540748.Hotel-Information)

![Breakfast, lunch, dinner served; Italian cuisine, garden views ](https://images.trvl-media.com/lodging/6000000/5180000/5172400/5172395/9f05cf5a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Panoramic Suite, Vineyard View](https://images.trvl-media.com/lodging/6000000/5180000/5172400/5172395/e04b84de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Panoramic Suite, Vineyard View | Vineyard view](https://images.trvl-media.com/lodging/6000000/5180000/5172400/5172395/91065266.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/6000000/5180000/5172400/5172395/70f4f37a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Castello di Fonterutoli Wine Resort

[](https://www.expedia.ca/Castellina-In-Chianti-Hotels-Castello-Di-Fonterutoli.h5172395.Hotel-Information)

Castellina in Chianti

9.4/10

Exceptional

(201)

"Clean room, courteous staff, and good winery"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Sangchun

CA $257

CA $289 total

includes taxes & fees

Dec 17 - Dec 18

[](https://www.expedia.ca/Castellina-In-Chianti-Hotels-Castello-Di-Fonterutoli.h5172395.Hotel-Information)

![Panoramic Apartment, Hill View (4) | Terrace/patio](https://images.trvl-media.com/lodging/43000000/42410000/42405300/42405254/6b1205b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/43000000/42410000/42405300/42405254/36cba6ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Panoramic Apartment (2) | Terrace/patio](https://images.trvl-media.com/lodging/43000000/42410000/42405300/42405254/975fa997.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Panoramic Apartment, Hill View (4)](https://images.trvl-media.com/lodging/43000000/42410000/42405300/42405254/d9f5b005.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Casa Vacanze Squarcialupi

[](https://www.expedia.ca/Castellina-In-Chianti-Hotels-Casa-Vacanze-Squarcialupi.h42405254.Hotel-Information)

Castellina in Chianti

8.0/10

Very good

(2)

"Staff was very helpful. Was a bit bummed the pool was closed as that was part of the reason for choosing the hotel. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jeffrey

CA $167

CA $193 total

includes taxes & fees

Dec 15 - Dec 16

[](https://www.expedia.ca/Castellina-In-Chianti-Hotels-Casa-Vacanze-Squarcialupi.h42405254.Hotel-Information)

![Aerial view](https://images.trvl-media.com/lodging/9000000/8160000/8157400/8157349/ce94a042.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Restaurant](https://images.trvl-media.com/lodging/9000000/8160000/8157400/8157349/79445c87.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Double Room | View from room](https://images.trvl-media.com/lodging/9000000/8160000/8157400/8157349/223c55fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/9000000/8160000/8157400/8157349/2a5b12cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Albergo Il Colombaio

[](https://www.expedia.ca/Castellina-In-Chianti-Hotels-Albergo-Il-Colombaio.h8157349.Hotel-Information)

Castellina in Chianti

8.4/10

Very good

(58)

"I was a little hesitant about staying outside a "major city," but I'm so glad we did. Very cute hotel and room. It was a short walk to the local town, which had lots of options for dinner and chianti tasting. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Christine

CA $187

CA $211 total

includes taxes & fees

Dec 21 - Dec 22

[](https://www.expedia.ca/Castellina-In-Chianti-Hotels-Albergo-Il-Colombaio.h8157349.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/66000000/65560000/65551600/65551595/24d91009.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/66000000/65560000/65551600/65551595/1601c656.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/cc13bd97.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/bf815143.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-La-Misura.h65551595.Hotel-Information)

Castellina in Chianti

10/10

Exceptional

(2)

"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-La-Misura.h65551595.Hotel-Information)

![9 bedrooms, free WiFi](https://images.trvl-media.com/lodging/77000000/76780000/76771500/76771413/0639021d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pool](https://images.trvl-media.com/lodging/77000000/76780000/76771500/76771413/413438c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/77000000/76780000/76771500/76771413/bc5dd1c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/77000000/76780000/76771500/76771413/1b75a533.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### VILLA IL PRINCIPE - Nine Bedroom Villa, Sleeps 18

[](https://www.expedia.ca/Castellina-In-Chianti-Hotels-VILLA-IL-PRINCIPE-Nine-Bedroom-Villa.h76771413.Hotel-Information)

Castellina in Chianti

[](https://www.expedia.ca/Castellina-In-Chianti-Hotels-VILLA-IL-PRINCIPE-Nine-Bedroom-Villa.h76771413.Hotel-Information)

![A heated pool](https://images.trvl-media.com/lodging/54000000/53940000/53936600/53936549/0ee653e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/54000000/53940000/53936600/53936549/7c752cd7.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/54000000/53940000/53936600/53936549/9a983ed0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### OLIVE TREES HOUSE WITH POOL

[](https://www.expedia.ca/Castellina-In-Chianti-Hotels-CASA-DEGLI-ULIVI-COTTAGE-WITH-SWIMMING-POOL.h53936549.Hotel-Information)

Castellina in Chianti

[](https://www.expedia.ca/Castellina-In-Chianti-Hotels-CASA-DEGLI-ULIVI-COTTAGE-WITH-SWIMMING-POOL.h53936549.Hotel-Information)

![Exterior detail](https://images.trvl-media.com/lodging/11000000/10510000/10507800/10507728/34e550c1.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)

![Daily buffet breakfast (EUR 20 per person)](https://images.trvl-media.com/lodging/11000000/10510000/10507800/10507728/4bb934b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Superior Double Room](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

[](https://www.expedia.ca/Florence-Hotels-Art-Hotel-Villa-Agape.h10507728.Hotel-Information)

Oltrarno

9.8/10

Exceptional

(1004)

"A beautiful hotel, extremely clean and with stunning gardens."

![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg)

Elizabeth

CA $143

CA $180 total

includes taxes & fees

Dec 16 - Dec 17

[](https://www.expedia.ca/Florence-Hotels-Art-Hotel-Villa-Agape.h10507728.Hotel-Information)

![Garden views, open daily](https://images.trvl-media.com/lodging/1000000/920000/913600/913526/e7798301.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/1000000/920000/913600/913526/d9d2a48e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment, Annex Building (stair access only) | Private kitchen](https://images.trvl-media.com/lodging/1000000/920000/913600/913526/8e79fd5c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment, Annex Building (stair access only) | Living area](https://images.trvl-media.com/lodging/1000000/920000/913600/913526/7426d88e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Globus Urban Hotel

[](https://www.expedia.ca/Florence-Hotels-Globus-Urban-Hotel.h913526.Hotel-Information)

Historic Centre of Florence

9.4/10

Exceptional

(1056)

"Staff were very friendly and helpful. Short walk to train station and main attractions. Highly recommend to anyone visiting Florence."

![Singapore](https://a.travel-assets.com/egds/marks/flags/sg.svg)

Wai Kong

CA $176

CA $217 total

includes taxes & fees

Dec 16 - Dec 17

[](https://www.expedia.ca/Florence-Hotels-Globus-Urban-Hotel.h913526.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=2025-12-28&endDate=2025-12-29&regionId=55534&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true)

## Top Castellina in Chianti Hotel Reviews

![Villa Neroli](https://images.trvl-media.com/lodging/1000000/590000/580400/580315/c19a6493_y.jpg)

### Villa Neroli

10/10 Excellent

"Staff is very kind."

[](https://expedia.ca/Florence-Hotels-Villa-Neroli.h580315.Hotel-Information)

![Plaza Hotel Lucchesi](https://images.trvl-media.com/lodging/1000000/10000/8800/8741/fc719366_y.jpg)

### Plaza Hotel Lucchesi

10/10 Excellent

"Clean, comfortable room/beds. Great location. Staff was very, very attentive. Very good breakfast. A special shout out to Concierge Extraordinaire Walter, who helped us out way beyond what I expected! I "

[](https://expedia.ca/Florence-Hotels-Plaza-Hotel-Lucchesi.h8741.Hotel-Information)

## Explore a world of travel with Expedia

- More ways to book

- [Book Winery Hotels in Castellina in Chianti on Expedia.it ](https://www.expedia.it/Castellina-In-Chianti-Hotel-Hotel-Winery.0-0-d55534-tHotelWinery.Guida-Viaggi-Filtro-Hotel)