Title: Castellina in Chianti Vacation Packages & Trips 2026 from CA $1,603 | 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)

![](https://images.trvl-media.com/place/55534/68deebc9-9310-492d-8f83-85d906ba54aa.jpg?impolicy=fcrop&w=1200&h=300&q=medium)

# Castellina in Chianti Vacation Packages

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#### Your Castellina in Chianti Vacation

An easy way to experience this city is with a tailor-made Castellina in Chianti vacation package. Base yourself in the neighborhood of Badia Coltibuono, which is good for families, nature and walking or go someplace else — our package deals are all about you. If sightseeing is on the cards during your trip to Castellina in Chianti, look around well-known attractions like [Isole e Olena Winery](https://www.expedia.ca/Isole-E-Olena-Winery-Barberino-Tavarnelle.d6230534.Vacation-Attraction), [Il Molino di Grace Winery](https://www.expedia.ca/Il-Molino-Di-Grace-Winery-Greve-in-Chianti.d6333570.Vacation-Attraction) and [Castello di Radda Winery](https://www.expedia.ca/Castello-Di-Radda-Winery-Radda-in-Chianti.d553248621532501476.Vacation-Attraction). Check out Expedia's wide range of travel options and begin planning your ultimate vacation to Castellina in Chianti now.

## Top Castellina in Chianti Vacation Deals

Price found within the past 48 hours. Click for updated prices.

![Hotel Duomo Firenze](https://images.trvl-media.com/lodging/3000000/2550000/2541700/2541603/89ed1f8e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hotel Duomo Firenze

Historic Centre of Florence

CA $1,603

per person

Jun 2 - Jun 6

found 1 day ago

Roundtrip flight included

Montreal (YMQ) to Florence (FLR)

9.2/10 Wonderful! (1,002 reviews)

Everything about this hotel is stellar. The room was excellent. The view was spectacular. The location is perfect. The breakfast was out of this world. And every single staff member was ready and willing to go the extra mile to make the stay a top tier experience! Even my 12yr old son told me to give this hotel “the max stars possible”. Oh, and I can’t forget to mention the sweetest and cutest Leone! We will absolutely be back to stay at the Hotel Duomo in the future!

Reviewed on Mar 23, 2026

![Residenza Florentia](https://images.trvl-media.com/lodging/2000000/1140000/1133600/1133528/da5e2175_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Residenza Florentia

Historic Centre of Florence

CA $1,844

per person

Jun 14 - Jun 20

found 19 hours ago

Roundtrip flight included

Halifax (YHZ) to Florence (FLR)

8.6/10 Excellent! (47 reviews)

Location, accommodations, and communication. Simple but comfortable. A basic facilities, and nice AC, elevator, and luggage storage.

Reviewed on Jun 12, 2025

![Hotel Berchielli](https://images.trvl-media.com/lodging/1000000/530000/521300/521260/3061994d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hotel Berchielli

Historic Centre of Florence

CA $2,419

per person

May 6 - May 11

found 13 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Florence (FLR)

9.4/10 Exceptional! (1,001 reviews)

Very good Breakfast with many food options. Great service !

Reviewed on Jan 21, 2026

![The Moon Boutique Hotel & Spa](https://images.trvl-media.com/lodging/23000000/22260000/22255000/22254976/a69619e4_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Moon Boutique Hotel & Spa

Historic Centre of Florence

CA $3,428

per person

Jun 12 - Jun 18

found 1 day ago

Roundtrip non-stop flight included

Halifax (YHZ) to Florence (FLR)

9.6/10 Exceptional! (512 reviews)

Staff excellent, room very good, food good. Facilities and location all good. Would be happy return and to recommend to family and friends. Thank you for such a pleasant stay

Reviewed on Mar 17, 2026

![Eurostars Florence Boutique](https://images.trvl-media.com/lodging/2000000/1170000/1167000/1166901/88283612_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Eurostars Florence Boutique

Historic Centre of Florence

CA $2,081

per person

May 9 - May 15

found 24 hours ago

Roundtrip flight included

Hamilton (YHM) to Florence (FLR)

8.6/10 Excellent! (483 reviews)

The room was clean and the staff very accommodating. The breakfast was quite sufficient and had a good variety. The location is great. It's a short walk from the square, shopping and from restaurants.

Reviewed on Dec 13, 2025

## Ready to book your vacation to Castellina in Chianti?

Choose your dates

## Castellina in Chianti Hotel Deals

![Hotel Machiavelli Palace](https://images.trvl-media.com/lodging/1000000/530000/521300/521248/ab2b96dc_y.jpg?impolicy=resizecrop&rw=340&ch=150)

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Hotel Machiavelli Palace

Via Nazionale 10 Florence FI

Fully refundableReserve now, pay when you stay

CA $114

CA $145 total

Mar 29 - Mar 30

includes taxes & fees

8.4/10 Very Good! (170 reviews)

was so perfect!

Reviewed on Mar 10, 2026

[](https://expedia.ca/Hotel-Search?startDate=29%2F03%2F2026&endDate=30%2F03%2F2026&selected=521248&PinnedHotelID=521248&HadPinnedHotel=true&regionId=55534)

![IQ Hotel Firenze](https://images.trvl-media.com/lodging/90000000/89040000/89035100/89035039/72f32f77_y.jpg?impolicy=resizecrop&rw=340&ch=150)

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IQ Hotel Firenze

Via Camillo Cavour, 88 Florence FI

Fully refundableReserve now, pay when you stay

CA $274

CA $324 total

Mar 26 - Mar 27

includes taxes & fees

9.6/10 Exceptional! (1,199 reviews)

Great location! Staff very helpful and food at hotel well priced and delicious! Loved the balcony with our room!!!

Reviewed on Mar 24, 2026

[](https://expedia.ca/Hotel-Search?startDate=26%2F03%2F2026&endDate=27%2F03%2F2026&selected=89035039&PinnedHotelID=89035039&HadPinnedHotel=true&regionId=55534)

![The Social Hub Florence Lavagnini](https://images.trvl-media.com/lodging/24000000/23200000/23198300/23198289/fdc60d68_y.jpg?impolicy=resizecrop&rw=340&ch=150)

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The Social Hub Florence Lavagnini

Viale Spartaco Lavagnini 70 72 Florence FI

Fully refundableReserve now, pay when you stay

CA $178

CA $219 total

Mar 29 - Mar 30

includes taxes & fees

9/10 Wonderful! (1,317 reviews)

Property is very clean and new with a beautiful lounge area.

Reviewed on Mar 24, 2026

[](https://expedia.ca/Hotel-Search?startDate=29%2F03%2F2026&endDate=30%2F03%2F2026&selected=23198289&PinnedHotelID=23198289&HadPinnedHotel=true&regionId=55534)

[See all 15,251 properties in Castellina in Chianti](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=26%2F03%2F2026&endDate=27%2F03%2F2026&regionId=55534)

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.

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

All Inclusive Vacations

[](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Beach Vacations

[](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Family Vacations

[](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Golf Vacations

[](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Luxury Vacations

[](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Romantic Vacations

[](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Ski Vacations

[](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click)

### Discover the most popular places to visit in Castellina in Chianti

![Castellina in Chianti showing farmland](https://images.trvl-media.com/place/553248635823420151/ee82ec03-289c-48c5-8d68-58e0a551a93c.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Buondonno Winery

You can enjoy a tasting or tour at Buondonno Winery during your travels to Castellina in Chianti. Discover the beautiful countryside and wineries in this quaint area. 

[](https://expedia.ca/Buondonno-Winery-Castellina-in-Chianti.d553248635823420151.Vacation-Attraction)

#### Casa Vinicola Luigi Cecchi

You can enjoy a tasting or tour at Casa Vinicola Luigi Cecchi during your travels to Castellina in Chianti. Discover the beautiful countryside in this walkable area, or enjoy its local tours. 

[](https://expedia.ca/Casa-Vinicola-Luigi-Cecchi-Castellina-in-Chianti.d6103262.Vacation-Attraction)

### What to do in Castellina in Chianti

![Siena, San Gimignano, Monteriggioni & Chianti from Florence](https://mediaim.expedia.com/localexpert/553041/def47daa-d183-43ae-81a6-3355ec60f5c9.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Siena, San Gimignano, Monteriggioni & Chianti from Florence

CA $72

per adult

**86%** of travellers recommend

[](https://expedia.ca/things-to-do/siena.a553041.activity-details)

![Florence: San Gimignano, Siena, Monteriggioni, Chianti & Lunch with Wine](https://mediaim.expedia.com/localexpert/329818/151bf7bf-958a-43e4-8bc4-b332a2585668.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Florence: San Gimignano, Siena, Monteriggioni, Chianti & Lunch with Wine

CA $124

per adult

**88%** of travellers recommend

[](https://expedia.ca/things-to-do/florence-san-gimignano.a329818.activity-details)

![Tuscany in 1 day: Pisa, San Gimignano and Siena with Lunch](https://mediaim.expedia.com/localexpert/236697/0f88e6e6-ef95-4a56-8618-2b7fc4f041a9.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Tuscany in 1 day from Florence: Pisa, San Gimignano & Siena with Lunch

CA $77

per adult

**78%** of travellers recommend

[](https://expedia.ca/things-to-do/tuscany-in-1-day-from-florence-pisa.a236697.activity-details)

[See all activities in Castellina in Chianti](https://expedia.ca/things-to-do/search?rid=55534)

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